CAS: 497-38-1; Bicyclo[2.2.1]Heptan-2-One

该化合物是双环切酮,具有僵硬,紧凑的结构,成为有机合成中有价值的中间体,其独特的诺伯伦框架有助于研究化学反应中的消毒和电子效应.该化合物在二类和阿尔代和其他循环反应中表现出高度的回活动性,作为制药,农用化学品和特殊聚合物的前体.在标准条件下和定义明确的立体化学学条件下,其稳定性适合不对称合成和催化研究.诺伯南-2-1也因其类似野味的香味而用于香味应用中.其多用途和可预测的再活动强调了其在精细化学和材料科学应用中的重要性.

结构式图片

相似化合物

497-37-0 1632-68-4 36779-79-0

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

1-methyl-4-nitrosobenzene endo-2-nitronorbornane acetic acid-[2]norbornylidenemethyl ester exo-2-norbornanolheptane-2,3-dionebicyclo2.2.1heptane-2,3-dione (1R,2S,4S)-2-Methyl-bicyclo[2.2.1]heptan-2-ol (2)2-p-Anisyl-norborneol-(2) 15H21NO2SC15H21NO2S

合成工艺路线路线简述

  • 合成目标产物 Norcamphor 主要起始原料 Bicyclo[2.2.1]Heptan-4-Ol
  • (文献来源)合成步骤主要原料 Bicyclo[2.2.1]Heptan-4-Ol
2-Nitronorbornane置于盐酸,Potassium Hydride体系中,化学反应生成 降樟脑
参考文献:Hwu,Jih Ru; Gilbert,Bryant A.,Journal Of The American Chemical Society,1991,Vol. 113,# 15,P. 5917-5918
标题:Hwu,Jih Ru; Gilbert,Bryant A.,Journal Of The American Chemical Society,1991,Vol. 113,# 15,P. 5917-5918

海关参考信息

专利信息


专利号:US-2003083352-A1
优先权日:2000-07-31
标 题 :Synthesis of imidazole intermediates
发明人:HELAL CHRISTOPHER J
权利人:PFIZER
摘要:The invention provides a method for synthesis of compounds of formula n n n wherein R 1 and R 19 are as defined. Compounds of formula 12 are useful as intermediates for synthesizing compounds having pharmacological activity inhibiting cdk5, cdk2, and GSK-3.

专利号:WO-0110798-A1
优先权日:1999-08-04
标题 :Solid phase synthesis of oxa- and thiazoles
发明人:BUNIN BARRY A; TUSHUP STEVEN P
权利人:CHEMRX ADVANCED TECHNOLOGIES I; BUNIN BARRY A; TUSHUP STEVEN P
摘要:Thia- and oxazole-4-carboxylic acid derivatives are prepared by solid phase synthesis, using intermediates of formula (α) where SS is a solid support and n is 0 or 1.

专利号:US-4331688-A
优先权日:1978-02-23
标题 :Therapeutic method for inhibiting gastric secretion by administration of 15-deoxy-16-hydroxy prostaglandins
发明人:KLUENDER HAROLD C; WOESSNER WARREN D; BIDDLECOM WILLIAM G
权利人:MILES LAB
摘要:Analogues of PGE 1 having the structural formula, ##STR1## in which J is R-hydroxymethylene or S-hydroxymethylene; R 1 is hydrogen; R 2 is hydrogen or together with R 4 is a methylene chain of 2 to 3 carbon atoms such that a cycloalkyl of 5 to 6 carbon atoms inclusive is formed; R 3 is hydrogen or methyl, or together with R 4 is a methylene or a lower alkylated methylene chain of 2 to 5 carbon atoms such that a cycloalkyl or a lower alkylated cycloalkyl of 4 to 7 carbon atoms inclusive is formed, or together with R 4 is bicycloalkyl or bicycloalkenyl moiety having the formula: ##STR2## such that a bicycloalkyl or bicycloalkenyl compound is formed, wherein m and n are integers having a value from 0 to 3, p is an integer having a value from 0 to 4 and q is an integer having a value of from 1 to 4 and wherein the double bond of such bicycloalkenyl is in the m, n, p, or q bridge; R 4 is hydrogen or methyl or together with R 2 or R 3 forms a cycloalkyl or bicycloalkyl or bicycloalkenyl as defined above, or together with R 5 is a methylene chain of 3 to 5 carbon atoms such that a cycloalkyl of 4 to 6 carbon atoms inclusive is formed; R 5 is selected from the group consisting of hydrogen, straight-chain alkyl having from 1 to 3 carbon atoms or together with R 4 forms a cycloalkyl as defined above; and R 6 is hydrogen or straight-chain alkyl having from 1 to 3 carbon atoms are disclosed. n PGE 1 ester analogues of the above formula, limited to the structures wherein two of R 2 , R 3 R 4 and R 5 form a cycloalkyl, lower alkylated cycloalkyl, bicycloalkyl or bicycloalkenyl are also disclosed. n The prostaglandin analogues selectively produce bronchodilation and decrease gastric secretion in vivo. n Methods of preparing the analogues and starting materials required in the synthesis of the analogues are also disclosed.

专利号:US-7399806-B2
优先权日:2003-06-26
标 题:Synthesis of photoresist polymers
发明人:BENOIT DIDIER; SAFIR ADAM; CHANG HAN-TING; CHARMOT DOMINIQUE; OKAMOTO KENJI; NISHIMURA ISAO; WANG YONG
权利人:SYMYX TECHNOLOGIES INC
摘要:The present invention is directed to the preparation of photoresist polymers via living free radical polymerization techniques. Sterically bulky ester monomers are utilized as the polymerization components. Use of chain transfer agents is included in polymerization processing conditions. Cleavage of polymer terminal end groups that include a heteroatom are described.

专利号:US-4132738-A
优先权日:1978-02-23
标 题:Preparation of 15-deoxy-16-hydroxyprostaglandins
发明人:KLUENDER HAROLD C; WOESSNER WARREN D; BIDDLECOM WILLIAM G
权利人:MILES LAB
摘要:Analogues of PGE 1 having the structural formula, ##STR1## in which J is R-hydroxymethylene or S-hydroxymethylene; R 1 is hydrogen; R 2 is hydrogen or together with R 4 is a methylene chain of 2 to 3 carbon atoms such that a cycloalkyl of 5 to 6 carbon atoms inclusive is formed; R 3 is hydrogen or methyl, or together with R 4 is a methylene or a lower alkylated methylene chain of 2 to 5 carbon atoms such that a cycloalkyl or a lower alkylated cycloalkyl of 4 to 7 carbon atoms inclusive is formed, or together with R 4 is bicycloalkyl or bicycloalkenyl moiety having the formula: ##STR2## SUCH THAT A BICYCLOALKYL OR BICYCLOALKENYL COMPOUND IS FORMED, WHEREIN M AND N ARE INTEGERS HAVING A VALUE FROM 0 TO 3, P IS AN INTEGER HAVING A VALUE FROM 0 TO 4 AND Q IS AN INTEGER HAVING A VALUE OF FROM 1 TO 4 AND WHEREIN THE DOUBLE BOND OF SUCH BICYCLOALKENYL IS IN THE M, N, P, OR Q BRIDGE; R 4 is hydrogen or methyl or together with R 2 or R 3 forms a cycloalkyl or bicycloalkyl or bicycloalkenyl as defined above, or together with R 5 is a methylene chain of 3 to 5 carbon atoms such that a cycloalkyl of 4 to 6 carbon atoms inclusive is formed; R 5 is selected from the group consisting of hydrogen, straight-chain alkyl having from 1 to 3 carbon atoms or together with R 4 forms a cycloalkyl as defined above; and R 6 is hydrogen or straight-chain alkyl having from 1 to 3 carbon atoms are disclosed. n Pge 1 ester analogues of the above formula, limited to the structures wherein two of R 2 , R 3 R 4 and R 5 form a cycloalkyl, lower alkylated cycloalkyl, bicycloalkyl or bicycloalkenyl are also disclosed. n The prostaglandin analogues selectively produce bronchodilation and decrease gastric secretion in vivo. n Methods of preparing the analogues and starting materials required in the synthesis of the analogues are also disclosed.

专利号:US-5726344-A
优先权日:1994-07-13
标题 :Enantiomeric enrichment of bicyclic alcohols
发明人:WEST J BLAIR; DEVRIES Keith
权利人:BEND RES INC
摘要:There is disclosed a two-stage enzymatically catalyzed reaction for the selective preparation of the (R)-endo-isomer of norbornenol from a mixture containing all four stereo- and regioisomers of norbornenol, as well as the synthesis of the intermediate product comprising the enantiomerically enriched mono-ester of (R)-endo-norbornenol and a diacid, and of the enantiomerically enriched saturated alcohol (R)-endo-norborneol. There is also disclosed a method for the production of (R)-endo-norborne-2-ol, by chemical reduction of either the enantiomerically enriched monoester and subsequent hydrolysis, or by hydrolysis of the enantiomerically enriched monoester and then chemical reduction.
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主要参考文献

[参考文献]: C Tetreau, Et Al. Conformational Relaxation In Hemoproteins: The Cytochrome P-450Cam Case. Biochemistry. 2000 Nov 21;39(46):14219-31.
[参考文献]: Edward J Basom, Et Al. Conformational Landscape And The Selectivity Of Cytochrome P450Cam. J Phys Chem B. 2015 Jun 4;119(22):6620-7.
[参考文献]: J R Collins, Et Al. Theoretical Study Of The Product Specificity In The Hydroxylation Of Camphor, Norcamphor, 5,5-Difluorocamphor, And Pericyclocamphanone By Cytochrome P-450Cam. J Biol Chem. 1988 Mar 5;263(7):3164-70.
[参考文献]: Lars Goerigk, Et Al. Calculation Of Electronic Circular Dichroism Spectra With Time-Dependent Double-Hybrid Density Functional Theory. J Phys Chem A. 2009 Jan 29;113(4):767-76.
[参考文献]: M B Bass, Et Al. Substrate Mobility In A Deeply Buried Active Site: Analysis Of Norcamphor Bound To Cytochrome P-450Cam As Determined By A 201-Psec Molecular Dynamics Simulation. Proteins. 1992 May;13(1):26-37.

合成参考文献


摘要:Shimizu, M., Science of Synthesis Knowledge Updates, (2010) 3, 48.
摘要:Braverman, S.; Cherkinsky, M., Science of Synthesis Knowledge Updates, (2014) 3, 204.
摘要:Vil’, V. A.; Bityukov, O. V.; Terent’ev, A. O., Science of Synthesis Knowledge Updates, (2019) 3, 397.
摘要:Zaidlewicz, M.; Pakulski, M. M., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 110.
摘要:U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals., NX#04039
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