(S)-3-cyclopentylthio-1,3-diphenylpropan-1-one | 1286762-17-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (S)-3-cyclopentylthio-1,3-diphenylpropan-1-one
• 英文别名: (S)-3-cyclopentylsulfanyl-1,3-diphenylpropan-1-one；(3S)-3-cyclopentylsulfanyl-1,3-diphenylpropan-1-one
• CAS: 1286762-17-1
• 化学式: C₂₀H₂₂OS
• 分子量: 310.46
• InChiKey: WTJHZHRTRCOHDF-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环戊硫醇 、 反式-查耳酮 在 (αR,αR)-α,α-双(叔丁基)-[2,2-联吡啶]-6,6-二甲醇 、 scandium tris(trifluoromethanesulfonate) 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 21.17h， 以84%的产率得到(S)-3-cyclopentylthio-1,3-diphenylpropan-1-one
  参考文献：
  名称：

  Sc(III)-Catalyzed Enantioselective Addition of Thiols to α,β-Unsaturated Ketones in Neutral Water

  摘要：

  This report concerns Lewis acid catalyzed enantioselective sulfa-Michael addition in neutral water by using a very efficient Sc(OTf)(3)/bipyridine 1 catalytic system. It is noteworthy that the protocol presented employs water as a reaction medium and allows us to obtain very high stereoselectivity and satisfactory yields for beta-keto sulphides deriving from aliphatic thiols. The recovery and reuse of both the aqueous medium and the catalytic system is also reported.

  DOI：

  10.1021/ol200379r

文献信息

• A Bifunctional Cinchona Alkaloid-Squaramide Catalyst for the Highly Enantioselective Conjugate Addition of Thiols to trans-Chalcones
  作者：Le Dai、Su-Xi Wang、Fen-Er Chen

  DOI：10.1002/adsc.201000334

  日期：2010.9.10

  A chiral squaramide catalysts‐promoted asymmetric sulfa‐Michael conjugated addition of thiols to trans‐chalcones is presented. Moderate to excellent yields and high enantioselectivities (up to 99% ee) were achieved under mild conditions.

  提出了一种手性方酰胺催化剂促进的不对称磺胺-迈克尔共轭硫醇到反式查尔酮的加成反应。在温和的条件下，获得了中度至优异的收率和高对映选择性（高达99％ee）。
• Sc(III)-Catalyzed Enantioselective Addition of Thiols to α,β-Unsaturated Ketones in Neutral Water
  作者：Simona Bonollo、Daniela Lanari、Ferdinando Pizzo、Luigi Vaccaro

  DOI：10.1021/ol200379r

  日期：2011.5.6

  This report concerns Lewis acid catalyzed enantioselective sulfa-Michael addition in neutral water by using a very efficient Sc(OTf)(3)/bipyridine 1 catalytic system. It is noteworthy that the protocol presented employs water as a reaction medium and allows us to obtain very high stereoselectivity and satisfactory yields for beta-keto sulphides deriving from aliphatic thiols. The recovery and reuse of both the aqueous medium and the catalytic system is also reported.