(S)-2-[bis(4-methylphenylthio)methyl]pyrrolidine

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (S)-2-[bis(4-methylphenylthio)methyl]pyrrolidine
• 英文别名: (2S)-2-[bis[(4-methylphenyl)sulfanyl]methyl]pyrrolidine
• 化学式: C₁₉H₂₃NS₂
• 分子量: 329.53
• InChiKey: KRUOZDWRKINZHZ-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-N-Boc-吡咯烷-2-甲醛 N-(叔丁氧羰基)-L-脯氨醛 在 indium(III) chloride 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (S)-2-[bis(4-methylphenylthio)methyl]pyrrolidine
  参考文献：
  名称：

  Inverse-Electron-Demand Hetero-Diels−Alder Reaction of β,γ-Unsaturated α-Ketophosphonates Catalyzed by Prolinal Dithioacetals

  摘要：

  Some novel prolinal dithioacetal derivatives were studied as catalysts for the inverse-electron-demand hetero-Diels-Alder reaction of enolizable aldehydes and beta,gamma-unsaturated alpha-ketophosphonates. The corresponding 5,6-dihydro-4H-pyran-2-ylphosphonates were obtained in good ee values (up to 94% ee).

  DOI：

  10.1021/ol071097y
• 作为试剂：
  描述：

  反式硝基苯乙烯 、 异丁醛 在 (S)-2-[bis(4-methylphenylthio)methyl]pyrrolidine 作用下， 以 二氯甲烷 为溶剂， 反应 72.07h， 以76%的产率得到
  参考文献：
  名称：

  脯氨酸二硫缩醛：在有机和水性介质中直接硝基-迈克尔加成的高效有机催化剂

  摘要：

  已经合成了一些新颖的脯氨二乙缩醛衍生物，并将其用作有机催化剂，用于将酮和醛直接迈克尔加成到硝基烯烃上。在有机和水性介质（二氯甲烷，水或盐水）中均获得了高对映选择性和非对映选择性。

  DOI：

  10.1016/j.tet.2017.10.008

文献信息

• Synthesis of prolinal dithioacetals as catalysts for the highly stereoselective Michael addition of ketones and aldehydes to β-nitrostyrenes
  作者：Tanmay Mandal、Cong-Gui Zhao

  DOI：10.1016/j.tetlet.2007.06.085

  日期：2007.8

  Catalytic highly enantioselective (up to > 99% ee) and diastereoselective (up to 99% de) direct Michael addition of ketones and aldehydes to beta-nitrostyrenes have been achieved with readily accessible and highly tunable prolinal dithioacetal catalysts. (c) 2007 Elsevier Ltd. All rights reserved.
• Prolinal dithioacetals: Highly efficient organocatalysts for the direct nitro-Michael additions in both organic and aqueous media
  作者：Tanmay Mandal、Wen Kuo、Matthew Su、Kartick Bhowmick、John C.-G. Zhao

  DOI：10.1016/j.tet.2017.10.008

  日期：2017.11

  Some novel prolinal dithioacetal derivatives have been synthesized and applied as the organocatalysts for the direct Michael addition of ketones and aldehydes to nitroalkenes. High enantioselectivities and diastereoselectivities have been obtained in both organic and aqueous media (dichloromethane, water, or brine).

  已经合成了一些新颖的脯氨二乙缩醛衍生物，并将其用作有机催化剂，用于将酮和醛直接迈克尔加成到硝基烯烃上。在有机和水性介质（二氯甲烷，水或盐水）中均获得了高对映选择性和非对映选择性。
• Inverse-Electron-Demand Hetero-Diels−Alder Reaction of β,γ-Unsaturated α-Ketophosphonates Catalyzed by Prolinal Dithioacetals
  作者：Sampak Samanta、Jonathan Krause、Tanmay Mandal、Cong-Gui Zhao

  DOI：10.1021/ol071097y

  日期：2007.7.1

  Some novel prolinal dithioacetal derivatives were studied as catalysts for the inverse-electron-demand hetero-Diels-Alder reaction of enolizable aldehydes and beta,gamma-unsaturated alpha-ketophosphonates. The corresponding 5,6-dihydro-4H-pyran-2-ylphosphonates were obtained in good ee values (up to 94% ee).