(R)-1-(cyclohexen-1-yl)-1,2-ethanediol | 129017-77-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-(cyclohexen-1-yl)-1,2-ethanediol
• 英文别名: (1R)-1-(cyclohexen-1-yl)ethane-1,2-diol
• CAS: 129017-77-2
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: LRJPEIMKYXSEHG-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1-(cyclohexen-1-yl)-1,2-ethanediol 在 4-二甲氨基吡啶 、 丙酸 叔丁基过氧化氢 、 正丁基锂 、 草酰氯 、 D-(-)-酒石酸二乙酯 、 TiO(iPr)4 、 四丁基氟化铵 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 邻二甲苯 为溶剂， 反应 41.0h， 生成 ethyl 2-[(2R,3R,4S)-2-[(Z)-pentadec-1-enyl]-1-oxaspiro[2.5]octan-4-yl]acetate
  参考文献：
  名称：

  构象受限的白三烯拮抗剂。正二十碳三烯D 4类似物的不对称合成。二。

  摘要：

  由环己酮制备手性二醇，并将其用于正白三烯D 4类似物的不对称合成。

  DOI：

  10.1016/s0040-4039(00)94325-9
• 作为产物：
  描述：

  methyl (-)-(αR)-α-hydroxycyclohex-1-eneacetate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以96%的产率得到(R)-1-(cyclohexen-1-yl)-1,2-ethanediol
  参考文献：
  名称：

  Asymmetric epoxidation of chiral allylic alcohols

  摘要：

  Two series of chiral allylic alcohols, derived from alpha,beta-unsaturated cyanohydrins, were subjected to asymmetric epoxidation under a variety of conditions. Both achiral (organic peracid, metal-catalyzed peroxide) and chiral (Sharpless titanium-tartrate system) oxidants were applied. Several three and all theoretically possible erythro epoxides were isolated in enantiomerically and diastereomerically pure form. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00327-8

文献信息

• Asymmetric induction in Darzens condensation by means of (−)-8-phenylmenthyl and (−)-menthyl auxiliaries
  作者：Ryukichi Takagi、Jyunji Kimura、Yoshihiro Shinohara、Yuko Ohba、Kyoko Takezono、Yoshikazu Hiraga、Satoshi Kojima、Katsuo Ohkata

  DOI：10.1039/a707310k

  日期：——

  Asymmetric Darzens condensation of benzaldehyde and various ketones has been investigated. The condensation of acetophenone, propiophenone and symmetric ketones with (–)-8-phenylmenthyl halogenoacetates 3a,b afforded the corresponding glycidic esters cis-12, cis-13 and 15–19 in 77–96% de, respectively, as the major products. Aza-Darzens condensation between N-benzylideneaniline and 3a occurred to give

  已经研究了苯甲醛和各种酮的不对称Darzens缩合。苯乙酮，丙苯酮和对称酮与（–）-8-苯基薄荷基卤代乙酸酯3a，b的缩合分别提供77-96％de的相应缩水甘油酯顺式-12，顺式-13和15-19，这是主要产物。在N-亚苄基苯胺和3a之间发生Aza-Darzens缩合，得到反式-氮丙啶21作为主要异构体，其de> 85％。顺式-12和18的主要非对映异构体的立体化学通过将其转化为已知的旋光性二醇22和24得以证实。顺式-12的主要产物的构型确定为2[R，3 - [R和18的是2 - [R。几何形状和地表选择性在初始醛醇型反应中可以理解为开链或非螯合的反平面的非平面过渡态模型。
• Highly enantioselective synthesis of multifunctionalized allylic building blocks via oxazaborolidine-catalyzed borane reduction
  作者：Byung Tae Cho、Sung Hye Shin

  DOI：10.1016/j.tet.2005.05.018

  日期：2005.7

  A simple and convenient synthesis of optically active alkenyl beta-hydroxy sulfides with high enantiomeric excess by CBS-oxazaborolidine-catalyzed borane reduction of the corresponding beta-keto sulfides and its application to synthesis of chiral alkenic diols have been established. (c) 2005 Elsevier Ltd. All rights reserved.
• SABOL, JEFFREY S.;CREGGE, ROBERT J., TETRAHEDRON LETT., 31,(1990) N, C. 27-30
  作者：SABOL, JEFFREY S.、CREGGE, ROBERT J.

  DOI：——

  日期：——
• Conformationally restricted leukotriene antagonists. Asymmetric synthesis of a nor-leokotriene D4 analog. II.
  作者：Jeffrey S Sabol、Robert J Cregge

  DOI：10.1016/s0040-4039(00)94325-9

  日期：1990.1

  Chiral diol is prepared from cyclohexanone and used in the asymmetric synthesis of nor-leukotriene D4 analog .

  由环己酮制备手性二醇，并将其用于正白三烯D 4类似物的不对称合成。
• Asymmetric epoxidation of chiral allylic alcohols
  作者：Erwin G.J.C. Warmerdam、Adrianus M.C.H. van den Nieuwendijk、Johannes Brussee、Chris G. Kruse、Arne van der Gen

  DOI：10.1016/0957-4166(96)00327-8

  日期：1996.9

  Two series of chiral allylic alcohols, derived from alpha,beta-unsaturated cyanohydrins, were subjected to asymmetric epoxidation under a variety of conditions. Both achiral (organic peracid, metal-catalyzed peroxide) and chiral (Sharpless titanium-tartrate system) oxidants were applied. Several three and all theoretically possible erythro epoxides were isolated in enantiomerically and diastereomerically pure form. Copyright (C) 1996 Elsevier Science Ltd