(R)-(2-cyclohexen-1-yl)acetyl chloride | 133775-35-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: (R)-(2-cyclohexen-1-yl)acetyl chloride
• 英文别名: (R)-2-cyclohexenylacetyl chloride；2-[(1R)-cyclohex-2-en-1-yl]acetyl chloride
• CAS: 133775-35-6
• 化学式: C₈H₁₁ClO
• 分子量: 158.628
• InChiKey: CBKJYMXEHUNIAH-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-(2-cyclohexen-1-yl)acetyl chloride 在 palladium on activated charcoal 盐酸 、 sodium azide 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 45.5h， 生成 (3aR,12R,12aR,12bS)-12-amino-2,3,3a,4,11,12,12a,12b-octahydro-10-hydroxyisoquino<2,1,8-lma>carbazol-5(1H)-one hydrochloride
  参考文献：
  名称：

  Synthesis of an enantiomerically pure aminoisoquinocarbazole with antiarrhythmic activity via lipase-catalyzed enantioselective transesterification

  摘要：

  Enantiomerically pure (R)-2-cydohexen-1-ol 5 was prepared via lipase-catalyzed enantioselective transesterification of 2-substituted cyclohexanol, and stereospecifically converted to (-)-(2-cyclohexenyl)acetic acid 4. Enantiomerically pure aminoisoquinocarbazole 1 (RS-2135) was synthesized stereoselectively from 4, using an intramolecular Dids-Alder reaction and Curtius rearrangement. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00199-1
• 作为产物：
  描述：

  2-iodo-1-cyclohexanol 在 sodium hydroxide 、 氯化亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 硝苯酚 作用下， 以 甲醇 、 异丙醚 、 苯 为溶剂， 反应 29.0h， 生成 (R)-(2-cyclohexen-1-yl)acetyl chloride
  参考文献：
  名称：

  Synthesis of an enantiomerically pure aminoisoquinocarbazole with antiarrhythmic activity via lipase-catalyzed enantioselective transesterification

  摘要：

  Enantiomerically pure (R)-2-cydohexen-1-ol 5 was prepared via lipase-catalyzed enantioselective transesterification of 2-substituted cyclohexanol, and stereospecifically converted to (-)-(2-cyclohexenyl)acetic acid 4. Enantiomerically pure aminoisoquinocarbazole 1 (RS-2135) was synthesized stereoselectively from 4, using an intramolecular Dids-Alder reaction and Curtius rearrangement. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00199-1

文献信息

• Indolobenzoquinoline derivatives, their preparation and their use as anti-arrhythmic drugs
  申请人：Sankyo Company Limited

  公开号：EP0415776A2

  公开（公告）日：1991-03-06

  Optically active compounds of formula (I): in which R1 is hydrogen or alkyl; Xb and Yb are hydrogen or hydroxy; and Z is -NRaRb in which Ra and Rb are hydrogen, alkyl or hydroxyalkyl, or a cyclic amino group; and pharmaceutically acceptable salts thereof have enhanced anti-arrhythmic activity and may be prepared by a stereospecific synthesis process.

  式(I)中的光学活性化合物：其中R1为氢或烷基；Xb和Yb为氢或羟基；Z为-NRaRb，其中Ra和Rb为氢、烷基或羟基烷基，或环状氨基；以及其药学上可接受的盐具有增强的抗心律失常活性，并可通过立体特异性合成过程制备。
• On Baldwin's kinetic barrier against 5-(enol-endo)-exo-trigonal closures: a comparison of ionic and analogous radical reactions, and a new synthesis of cyclopentanones
  作者：Derrick L. J. Clive、David R. Cheshire

  DOI：10.1039/c39870001520

  日期：——

  The kinetic barrier that impedes ionic 5-(enol-endo)-exo-trigonal closures does not play such a dominant role in the case of α-oxo radicals (17); these radicals cyclize directly to cyclopentanones in a process that constitutes a synthetic method for converting allylic alcohols (12) into bicyclo[n.3.0]alkanones (19).

  在α-氧代自由基的情况下，阻碍离子性5-（烯醇-内）-外-三角封闭的动力学屏障不发挥这种主导作用（17）。这些基团直接环化成环戊酮在构成的合成方法，用于将烯丙基醇（过程12）插入双环[ Ñ .3.0]烷酮（19）。
• Preparation of optically active cyclohexenol and cyclohexenyl acetic acid via an enzymatic process followed by a rearrangement reaction and their use as intermediates in the synthesis of indolobenzoquinoline derivatives
  申请人：Sankyo Company Limited

  公开号：EP0674008A1

  公开（公告）日：1995-09-27

  A process for the production of optically active compounds of formula (VIII) and III which process comprises the following steps: (a) reaction, in the presence of a lipase, of a dl-trans-cyclohexanol compound of formula (XXI): to give an optically active compound of formula (XXIV) followed by b) an oxidation, c) an elimination and d) a hydrolyzation reaction to give the optically active compound VIII and rearranging the compound VIII with orthoester to the optically active compound III. Compounds VIII and III are intermediates in the synthesis of optically active compounds of formula I

  一种生产式（VIII）和式（III）光学活性化合物的工艺 该工艺包括以下步骤 (a) 式(XXI)的二反式环己醇化合物在脂肪酶存在下进行反应： 得到式（XXIV）的光学活性化合物 然后进行 b) 氧化反应、c) 消去反应和 d) 水解反应，得到光学活性化合物 VIII，并将化合物 VIII 与原酯重新排列，得到光学活性化合物 III。 化合物 VIII 和 III 是合成具有光学活性的式 I 化合物的中间体。
• Synthesis of an enantiomerically pure aminoisoquinocarbazole with antiarrhythmic activity via lipase-catalyzed enantioselective transesterification
  作者：Tetuya Fukazawa、Yasuo Shimoji、Toshihiko Hashimoto

  DOI：10.1016/0957-4166(96)00199-1

  日期：1996.6

  Enantiomerically pure (R)-2-cydohexen-1-ol 5 was prepared via lipase-catalyzed enantioselective transesterification of 2-substituted cyclohexanol, and stereospecifically converted to (-)-(2-cyclohexenyl)acetic acid 4. Enantiomerically pure aminoisoquinocarbazole 1 (RS-2135) was synthesized stereoselectively from 4, using an intramolecular Dids-Alder reaction and Curtius rearrangement. Copyright (C) 1996 Elsevier Science Ltd