CAS: 7785-70-8; (1R,5R)-2,6,6-Trimethylbicyclo[3.1.1]Hept-2-Ene

该化合物是单体,是α-皮内体的两个对应体之一,其特征是其绝对配置(1R),这种双环有机化合物是许多基本油类中的一个关键成分,特别是来自金刚树的油类,其高纯度和界定的立体化学使其在手工业合成,香气配方和作为分析化学参考标准中具有价值. (1R)-α-皮内物在氧化和异构反应中表现出显著的反动作用,作为精细化学品的前体.其对应纯度确保了研究和工业过程的一贯性,在这些过程中,立体选择性至关重要.该化合物的特征是其低味阈值和独特的松状芳香.

结构式图片

物理性质

欧盟法规

欧盟化妆品法规附录三-限用物质清单REACH注册ECHA物质ECHA物质C&L通报REACH预注册

上下游产品

ethanol R,2S,3R)-3-(toluene-sulfonyl-(4)-oxy)-pinane(1R,2S,3R)-3-(toluene-sulfonyl-(4)-oxy)-pinane sodium ethanolate R,2R,3S)-3-(toluene-sulfonyl-(4)-oxy)-pinane(1R,2R,3S)-3-(toluene-sulfonyl-(4)-oxy)-pinane (E,E)-2,6-dimethyl-2,4,6-°Ctatriene limonene. 1-methyl-4-isopropyl-1,3-cyclohexadiene dl-camphene

合成工艺路线路线简述

  • 合成目标产物 (1R)-(+)-Alpha-Pinene 主要起始原料 [(1R,2S,3R,5R)-2,6,6-Trimethylbicyclo[3.1.1]Hept-3-Yl]Borane
  • (文献来源)合成步骤主要原料 [(1R,2S,3R,5R)-2,6,6-Trimethylbicyclo[3.1.1]Hept-3-Yl]Borane
Diisopinocampheylborane置于苯甲醛,三氟化硼乙醚体系中,化学反应 1.0H,以71%的收率获得产物(+)-α-蒎烯
参考文献:Pin烯基联吡啶二醇和联吡啶的改进高效合成
标题:Pin烯基联吡啶二醇和联吡啶的改进高效合成
摘要:据报道,基于pin烯的两种联吡啶二醇和联吡啶的合成得到了改进和有效.pin烯基吡啶酮与磷酰氯的密封管压反应首次产生了pin烯基2-氯吡啶非常好的收率(95%),这使得合成pin烯基联吡啶二醇成为一种非常便宜且高收率的方法.此外,开发了一种高效的反应条件,用于氯吡啶与ni(0)的均相偶联,从而以高收率(84%)提供了基于pin烯的联吡啶.这些新证明的氯吡啶的密封管压氯化和均偶联反应为合成基于pin烯的联吡啶提供了极其有效的途径.
DOI:10.1016/j.Tetlet.2016.03.075

海关参考信息

专利信息


专利号:US-4140708-A
优先权日:1975-10-16
标 题 :Asymmetric synthesis of optically active prostaglandins
发明人:CHADHA NARESH K; PARTRIDGE JR JOHN J; USKOKOVIC MILAN R
权利人:HOFFMANN LA ROCHE
摘要:An asymmetric synthesis of optically active prostaglandin F 2 α from cyclopentadiene including intermediates in this synthesis.

专利号:US-3933892-A
优先权日:1973-02-12
标题 :Asymmetric synthesis of optically active prostaglandins
发明人:CHADHA NARESH KUMAR; PARTRIDGE JR JOHN JOSEPH; USKOKOVIC MILAN RADOJE
权利人:HOFFMANN LA ROCHE
摘要:An asymmetric synthesis of optically active prostaglandin F 2 .sub.α from cyclopentadiene including intermediates in this synthesis.

专利号:WO-0172706-A1
优先权日:2000-03-28
标题 :Synthesis of [r-(r*,r*)]-2-(4-fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1h-pyrrole-1-heptanoic acid hemi calcium salt (atorvastatin)
发明人:SAMBASIVAN GANESH; SRIDHARAN MADHAVAN; PADUDEVASTANA SATHYASHANKER; POORNAPRAJNA ACHARYA; MATHEW JOY; SRINATH SUMITHRA; NAIR SATHEESH
权利人:BIOCON LTD; SAMBASIVAN GANESH; SRIDHARAN MADHAVAN; PADUDEVASTANA SATHYASHANKER; POORNAPRAJNA ACHARYA; MATHEW JOY; SRINATH SUMITHRA; NAIR SATHEESH
摘要:The present invention discusses a novel process for the synthesis of [R-(R*,R*)]-2-(4-fluorophenyl)-B,D-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic acid hemi calcium salt by using 4-fluoro-α-[2-methyl-1-oxopropyl]η-oxo-N-β-diphenylbenzene butaneamide with (4R)-methyl 6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-3-acetate. The compound so prepared is useful as inhibitors of the enzyme HMG-CoA reductase and are thus used as hypolipidemic and hypocholesterolemic agents.

专利号:US-5463131-A
优先权日:1994-06-30
标题 :Synthesis of organohaloboranes and alkoxyorganoboranes
发明人:BURKHARDT ELIZABETH R
权利人:MINE SAFETY APPLIANCES CO
摘要:A one-step process is provided for the synthesis of organohaloboranes, including diisopinocampheylchloroborane, and alkoxyorganoboranes. The present process does not utilize a thermally unstable ether adduct or a malodorous dimethyl sulfide adduct as required in prior processes. In general, the organohaloboranes are synthesized in a single reactor by reacting olefin(s) and/or alkyne(s) with boron trihalide and diborane. Alkoxyorganoboranes are synthesized in a single reactor by reacting olefin(s) and/or alkyne(s) with alkylborate and diborane.

专利号:US-6380416-B2
优先权日:1997-06-13
标题:Asymmetric synthesis catalyzed by transition metal complexes with rigid chiral ligands
发明人:ZHANG XUMU
权利人:PENN STATE RES FOUND
摘要:This invention is to develop novel transition metal catalysts for the practical synthesis of important chiral molecules. The invention emphasizes asymmetric catalysis based on chiral bidentate phosphine ligands with cyclic ring structures which could be used to restrict conformational flexibility of the ligands and thus the efficiency of chiral transfer can be enhanced through the ligand rigidity.

专利号:EP-1030854-B1
优先权日:1997-11-12
标题 :Catalysts for asymmetric synthesis containing rigid chiral ligands
发明人:ZHANG XUMU
权利人:PENN STATE RES FOUND
摘要:This invention is to develop novel transition metal catalysts for the pratical synthesis of important chiral molecules. The invention emphasizes asymmetric catalysis based on chiral bidentate phosphine ligands with cyclic ring structures which could be used to restrict conformational flexibility of the ligands and thus the efficiency of chiral transfer can be enhanced through the ligand rigidity.
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合成参考文献


摘要:Drabowicz, J.; Kiełbasiński, P.; Łyżwa, P.; Mikołajczyk, M.; Zając, A., Science of Synthesis, (2009) 42, 741.
摘要:Chessum, N.; Couty, S.; Jones, K., Science of Synthesis, (2009) 48, 281.
摘要:Yus, M.; Foubelo, F., Science of Synthesis, (2010) 47, 1072.
摘要:Chessum, N.; Couty, S.; Jones, K., Science of Synthesis, (2009) 48, 309.
摘要:Chessum, N.; Couty, S.; Jones, K., Science of Synthesis, (2009) 48, 325.
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