(2S,3R)-2,3-epoxy-3-cyclohexylpropiophenone | 206276-07-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-2,3-epoxy-3-cyclohexylpropiophenone
• 英文别名: (2S,3R)-1-phenyl-2,3-epoxy-3-cyclohexylpropan-1-one；Methanone, [(2S,3R)-3-cyclohexyloxiranyl]phenyl-；[(2S,3R)-3-cyclohexyloxiran-2-yl]-phenylmethanone
• CAS: 206276-07-5
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: BZLSWYRUMORNDX-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2,3-epoxy-3-cyclohexylpropiophenone 在 间氯过氧苯甲酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以80%的产率得到phenyl (2S,3R)-2,3-epoxy-3-cyclohexylpropionate
  参考文献：
  名称：

  Optically active epoxy compounds and processes for their production

  摘要：

  公开号：

  EP1403260B1
• 作为产物：
  描述：

  3-环己基-1-苯基丙-2-烯-1-酮 在 lanthanum(III) isopropoxide 、 S-1,1'-联-2-萘酚 、 过氧化氢异丙苯 、 三苯基氧化膦 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以80%的产率得到(2S,3R)-2,3-epoxy-3-cyclohexylpropiophenone
  参考文献：
  名称：

  Optically active epoxy compounds and processes for their production

  摘要：

  公开号：

  EP1403260B1

文献信息

• Catalytic asymmetric Darzens condensation under phase-transfer-catalyzed conditions
  作者：Shigeru Arai、Takayuki Shioiri

  DOI：10.1016/s0040-4039(98)00081-1

  日期：1998.4

  The catalytic asymmetric Darzens condensation promoted by the quaternary ammonium salt (PTC A) derived from cinchonine as a phase-transfer catalyst is described. Treatment of phenacyl chloride with various aldehydes under mild reaction conditions afforded the corresponding desired product in good yield with good to moderate enantiomeric excess.

  描述了由金鸡宁衍生的季铵盐（PTC A）作为相转移催化剂促进的催化不对称Darzens缩合反应。在温和的反应条件下用各种醛处理苯甲酰氯，以高收率得到适当的对映体，得到相应的所需产物。
• Phase-transfer-catalyzed asymmetric Darzens reaction
  作者：Shigeru Arai、Yoshiki Shirai、Toshimasa Ishida、Takayuki Shioiri

  DOI：10.1016/s0040-4020(99)00213-6

  日期：1999.5

  Catalytic asymmetric Darzens reaction promoted by a chiral phase-transfer catalyst derived from cinchonine is described. The desired α,β-epoxy ketones were obtained by use of α-chloro acyclic and cyclic ketones as substrates with moderate to high enantiomeric excesses under mild reaction conditions. This methodology can be quite an effective protocol for practical asymmetric synthesis.

  描述了由辛可宁衍生的手性相转移催化剂促进的催化不对称Darzens反应。在温和的反应条件下，以α-氯无环和环状酮为底物，对映体过量到中度到高，可以得到所需的α，β-环氧酮。对于实际的不对称合成，该方法可能是非常有效的协议。
• Adger, Brian M.; Barkley, James V.; Bergeron, Sophie, Journal of the Chemical Society. Perkin transactions I, 1997, # 23, p. 3501 - 3507
  作者：Adger, Brian M.、Barkley, James V.、Bergeron, Sophie、Cappi, Michael W.、Flowerdew, Benjamin E.、Jackson, Mark P.、McCague, Ray、Nugent, Thomas C.、Roberts, Stanley M.

  DOI：——

  日期：——
• Mechanism and Conditions for Highly Enantioselective Epoxidation of α,β-Enones Using Charge-Accelerated Catalysis by a Rigid Quaternary Ammonium Salt
  作者：E. J. Corey、Fu-Yao Zhang

  DOI：10.1021/ol990964z

  日期：1999.10.1

  [GRAPHICS]Highly enantioselective (up to 130:1) epoxidation of a variety of alpha,beta-enones to form alpha,beta-epoxy ketones is described along with a rational analysis of the mechanistic basis for this strong absolute stereochemical control by the chiral catalyst 2.
• Asymmetric Epoxidation of a,b-Unsaturated Ketones with Hydrogen Peroxide Catalyzed by Axially Chiral Guanidine Base
  作者：Masahiro Terada、Megumi Nakano

  DOI：10.3987/com-08-s(n)105

  日期：——

  The enantioselective epoxidation of alpha,beta-unsaturated ketones with hydrogen peroxide was demonstrated using axially chiral guanidine as a base catalyst. Hydrogen peroxide can be utilized as a cost-effective and atom-efficient oxidant in the present catalytic epoxidation even under heterogeneous conditions. The newly developed axially chiral guanidine base bearing an additional central chirality functions as an efficient catalyst to provide epoxides in 51-65% ee.