CAS: 1008-76-0; 5-Phenyloxolan-2-One

该化合物是一个循环酯(内酯),在氧-2-1环的5个位置上有一个替代苯基的替代体.由于有机合成作为制药,农用化学和精细化学材料的构件的多功能性,该化合物对有机合成具有兴趣.该苯基组增强了其在环开和功能化反应中的回活动性,使其对构建复杂的分子框架具有价值.其稳定的内酯结构确保了在标准条件下的处理和储存的方便性.研究人员在不对称合成中使用5-苯丙诺--2-1,并将其作为手性中间体的前体.该化合物的固定立体化学特性及其与各种反应条件的兼容性进一步促进了其在合成应用中的实用性.

结构式图片

相似化合物

36866-66-7 1318254-30-6 1885-28-5

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上下游产品

styrene oxide ethanol sodium diethylmalonate α-bromoacetophenone4-hydroxy-4-phenyl-1-(piperidin-1-yl)butan-1-one N-cyclohexyl-4-hydroxy-4-phenylbutanamide 1-(4-methylphenyl)-5-phenylpyrrolidin-2-one 1,5-diphenylpyrrolidin-2-one

合成工艺路线路线简述

  • 合成目标产物 Gamma-Phenyl-Gamma-Butyrolactone 主要起始原料 1-Phenyl-1,4-Butanediol
  • (文献来源)合成步骤主要原料 1-Phenyl-1,4-Butanediol
📜3-苯基环丁酮置于过氧化氢异丙苯,(R)-1,1'-Bi-2-Naphthol,二甲基氯化铝体系中,用 甲苯 用作溶剂,化学反应生成γ-苯基-γ-丁内酯
参考文献:铝催化不对称baeyer-Villiger反应中的配体效应
标题:铝催化不对称baeyer-Villiger反应中的配体效应
摘要:外消旋和手性环丁酮的不对称baeyer-Villiger氧化反应可以用基于铝的手性路易斯酸进行,从而产生具有高对映选择性的产品.通过使用取代的binol衍生物作为配体,获得了显着的催化剂效率,并获得了ee高达84%的γ-丁内酯.研发了配体的电子性质与反应的对映选择性之间的关系,从而使人们更好地理解了在铝催化的氧化转化中实现非常好对映选择性的要求.
Doi:10.1016/j.Tet.2005.12.080

专利信息


专利号:US-8598346-B2
优先权日:2008-07-16
标 题 :Synthesis of cyclic amidines
发明人:LENTZEN GEORG; NEUHAUS THORSTEN
权利人:LENTZEN GEORG; NEUHAUS THORSTEN; BITOP AG
摘要:The invention relates to an innovative method for synthesis of cyclic amidines. The synthesis starts from a β-, γ- or δ-lactone which is twofold brominated. After esterification of the carboxyl function, the bromine atoms are nucleophilically substituted and the corresponding diamino compound is obtained. The ring closure to the cyclic amidine is accomplished subsequently by reaction with orthoester, imidate or thioimidate. Owing to interposing additional steps for recovery of the diamino compound in enantiomerically pure form, the enantiomers of the cyclic amidines can be stereoselectively synthesized.

专利号:EP-2883866-A1
优先权日:2012-08-13
标题 :INTERMEDIATE FOR SYNTHESIS OF 1-(2-DEOXY-2-FLUORO-4-THIO-beta-D-ARABINOFURANOSYL) CYTOSINE, INTERMEDIATE FOR SYNTHESIS OF THIONUCLEOSIDE, AND METHODS FOR PRODUCING THESE INTERMEDIATES

专利号:WO-2014027658-A1
优先权日:2012-08-13
标题 :INTERMEDIATE FOR SYNTHESIS OF 1-(2-DEOXY-2-FLUORO-4-THIO-β-D-ARABINOFURANOSYL) CYTOSINE, INTERMEDIATE FOR SYNTHESIS OF THIONUCLEOSIDE, AND METHODS FOR PRODUCING THESE INTERMEDIATES

专利号:MX-2015001935-A
优先权日:2012-08-13
标 题 :INTERMEDIARY FOR SYNTHESIS OF 1- (2-DEOXI-2-FLUORO-4-TIO-BETA-D-A RABINOFURANOSIL) CITOSINE, INTERMEDIARY FOR SYNTHESIS OF TIONUCLEOSIDE AND METHODS TO PRODUCE THESE INTERMEDIARIES.

专利号:ES-2718307-T3
优先权日:2012-08-13
标题 :Intermediate for the synthesis of 1- (2-deoxy-2-fluoro-4-thio-beta-d-arabinofuranosyl) cytosine, intermediate for the synthesis of thionucleoside and methods to produce these intermediates

专利号:US-6028224-A
优先权日:1998-06-22
标 题 :Fluoxetine process from benzoylpropionic acid
发明人:HILBORN JAMES WALLACE; JURGENS ALEX ROGER; SENANAYAKE CHRIS HUGH
权利人:SEPRACOR INC
摘要:A synthesis of fluoxetine is disclosed. The process begins with a lower alkyl ester of 3-benzoylpropionic acid, which is reduced in the presence of a chiral ligand to produce the corresponding γ-hydroxy ester, and the ester is cleaved. The free acid is then condensed with the alcohol to form a γ-lactone, which is treated with ammonia to provide the γ-hydroxy amide. The amide undergoes a Hoffman rearrangement to provide a 2-oxo-1,3 oxazine, which is reduced to 3-(methylamino)-1-phenyl-1-propanol. The alcohol is deprotonated and reacted with a 4-chloro- or 4-fluoro benzotrifluoride to provide fluoxetine free base.

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📌 第三方产品分析报告

✅ COA系统入驻 | 共享模式

主要参考文献

参考标题:Synthesis Of Cyclic Amidines
摘要:The Invention Relates To An Innovative Method For Synthesis Of Cyclic Amidines. The Synthesis Starts From A β-, γ- Or δ-Lactone Which Is Twofold Brominated. After Esterification Of The Carboxyl Function, The Bromine Atoms Are Nucleophilically Substituted And The Corresponding Diamino Compound Is Obtained. The Ring Closure To The Cyclic Amidine Is Accomplished Subsequently By Reaction With Orthoester, Imidate Or Thioimidate. Owing To Interposing Additional Steps For Recovery Of The Diamino Compound In Enantiomerically Pure Form, The Enantiomers Of The Cyclic Amidines Can Be Stereoselectively Synthesized.

合成参考文献


参考文献:10.1515/znc-2005-9-1019
摘要:Wood WF, Walsh A, Seyjagat J, Weldon PJ. Volatile compounds in shoulder gland secretions of male flying foxes, genus Pteropus (Pteropodidae, Chiroptera). Z Naturforsch C J Biosci. 2005 Sep;60(9-10):779–84. doi: 10.1515/znc-2005-9-1019.
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