(4S,8S)-8,9-环氧-p-薄荷-1-烯 | 62660-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 中文名称: (4S,8S)-8,9-环氧-p-薄荷-1-烯
• 英文名称: (4S,8S)-8,9-Epoxy-p-menth-1-ene
• 英文别名: Oxirane, 2-methyl-2-[(1S)-4-methyl-3-cyclohexen-1-yl]-, (2S)-；(2S)-2-methyl-2-[(1S)-4-methylcyclohex-3-en-1-yl]oxirane
• CAS: 62660-05-3
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: PJGRMBOWSWHGDV-NXEZZACHSA-N

物化性质

• 沸点：
  197.3±29.0 °C(Predicted)
• 密度：
  0.987±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4S,8S)-8,9-环氧-p-薄荷-1-烯 在 chromium(VI) oxide 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (-)-(4R,8S)-8,9-epoxyisopiperitenone
  参考文献：
  名称：

  Modified Monoterpenes from Biotransformation of (−)-Isopiperitenone by Suspension Cell Culture of Mentha piperita

  摘要：

  The biotransformation of (-)-(4R)-isopiperitenone (1) by suspension cell culture of Mentha piperita yielded three new hydroxylated derivatives, 4-6, and two new epoxidized derivatives, 7 and 8. (-)-7-Hydroxyisopiperitenone (2) and its glucoside were previously isolated from the culture. The structures of 4-8 were elucidated using spectral methods, and their absolute stereochemistry was established by NMR experiments and correlation with compounds of known configuration.

  DOI：

  10.1021/np970388k
• 作为产物：
  描述：

  (1R,2R,4S,8S)-1,2-dibromo-8,9-epoxy-p-menthane 在 锌 作用下， 生成 (4S,8S)-8,9-环氧-p-薄荷-1-烯
  参考文献：
  名称：

  Modified Monoterpenes from Biotransformation of (−)-Isopiperitenone by Suspension Cell Culture of Mentha piperita

  摘要：

  The biotransformation of (-)-(4R)-isopiperitenone (1) by suspension cell culture of Mentha piperita yielded three new hydroxylated derivatives, 4-6, and two new epoxidized derivatives, 7 and 8. (-)-7-Hydroxyisopiperitenone (2) and its glucoside were previously isolated from the culture. The structures of 4-8 were elucidated using spectral methods, and their absolute stereochemistry was established by NMR experiments and correlation with compounds of known configuration.

  DOI：

  10.1021/np970388k

文献信息

• Hydrolytic kinetic resolution of cyclic substrates
  申请人：——

  公开号：US20020032338A1

  公开（公告）日：2002-03-14

  The present invention relates to a process for stereoselective or regioselective chemical synthesis which generally comprises reacting a nucleophile and a chiral or prochiral cyclic substrate in the presence of a non-racemic, chiral catalyst to produce a stereoisomerically- and/or regioisomerically-enriched product. The present invention also relates to hydrolytic kinetic resolutions of racemic and diastereomeric mixtures of epoxides.

  本发明涉及一种立体选择性或区域选择性化学合成的方法，通常包括在非外消旋手性催化剂的存在下，将亲核试剂和手性或前手性环状底物反应，以产生立体异构体和/或区域异构体富集的产物。本发明还涉及外消旋环氧化物的混合物的水解动力学分离。
• Nucleophilic kinetic resolution of cyclic substrates using silyl azides
  申请人：——

  公开号：US20040044233A1

  公开（公告）日：2004-03-04

  The present invention relates to a process for stereoselective or regioselective chemical synthesis which generally comprises reacting a nucleophile and a chiral or prochiral cyclic substrate in the presence of a non-racemic, chiral catalyst to produce a stereoisomerically- and/or regioisomerically-enriched product. The present invention also relates to hydrolytic kinetic resolutions of racemic and diastereomeric mixtures of epoxides.

  本发明涉及一种立体选择性或区域选择性化学合成的过程，通常包括在非外消旋、手性催化剂的存在下，将亲核试剂和手性或前手性环状底物反应，以产生立体异构体和/或区域异构体富集的产物。本发明还涉及外消旋和二对映异构体环氧化物的水解动力学分辨。
• Microbiological transformations. 27. The first examples for preparative-scale enantioselective or diastereoselective epoxide hydrolyses using microorganisms. An unequivocal access to all four bisabolol stereoisomers
  作者：X. J. Chen、A. Archelas、R. Furstoss

  DOI：10.1021/jo00072a043

  日期：1993.9
• CrIII(salen) impregnated on silica for asymmetric ring opening reactions and its recovery via desorption/re-impregnation
  作者：Bart M.L. Dioos、Pierre A. Jacobs

  DOI：10.1016/j.tetlet.2003.09.203

  日期：2003.12

  The impregnation of Cr-III(salen) complexes on silica resulted in a heterogeneous catalyst for the asymmetric ring opening (ARO) reaction of epoxides with good selectivity and acceptable activity. As became apparent from a series of 10 successive batch tests in the ARO reaction of 1,2-epoxyhexane, leaching was limited, while catalytic activity and selectivity were acceptable. Though the support suffered from abrasion in the batch reactor, 80% of the catalyst was easily recoverable via simple extraction from the used solid catalyst and entirely transferable onto a fresh carrier via impregnation. It was shown that 80% of the leached catalyst at the end of the tests could be transformed into a fresh heterogeneous catalyst as well. (C) 2003 Elsevier Ltd. All rights reserved.
• STEREOSELECTIVE RING OPENING REACTIONS
  申请人：PRESIDENT AND FELLOWS OF HARVARD COLLEGE

  公开号：EP0817765A1

  公开（公告）日：1998-01-14