(R_S)-2-phenylpropyl-2-sulfinamide | 1428365-94-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R_S)-2-phenylpropyl-2-sulfinamide
• 英文别名: (R)-2-phenylpropane-2-sulfinamide
• CAS: 1428365-94-9
• 化学式: C₉H₁₃NOS
• 分子量: 183.274
• InChiKey: XEBWBUKJPSEQOL-GFCCVEGCSA-N

物化性质

• 沸点：
  342.6±35.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R_S)-2-phenylpropyl-2-sulfinamide 在 titanium(IV) tetraethanolate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (R)-N-[(1S)-1-(4-fluorophenyl)but-3-enyl]-2-phenylpropane-2-sulfinamide
  参考文献：
  名称：

  Design, Synthesis, and Applications of Chiral N-2-Phenyl-2-propyl Sulfinyl Imines for Group-Assisted Purification (GAP) Asymmetric Synthesis

  摘要：

  A new chiral (Rs)-2-phenyl-2-propyl sulfinamide has been designed and synthesized; its derived aldimines and ketimines have been applied for asymmetric addition reaction with allylmagnesium bromide. The reaction was conveniently performed at room temperature to give a series of homoallylic amines in high yields (up to quant) and diastereoselectivity (up to >99% de). The pure products were obtained by relying on group-assisted purification (GAP) chemistry to avoid traditional purification methods of column chromatography or recrystallization. The conversion of disulfide to (R(s))-thiosulfinate which contains a newly generated polar group was also confirmed to be of the GAP chemistry in which washing crude product can generate pure enantiomer. The absolute stereochemistry has been determined by X-ray analysis.

  DOI：

  10.1021/jo400354r
• 作为产物：
  描述：

  Α,Α-二甲基苄硫醇 在 正丁基锂 、 bis(acetylacetonate)oxovanadium 、 (1S,2R)-1-[(3,5-di-tert-butyl-2-hydroxybenzylidene)amino]-2-indanol 、 四丁基氟化铵 、 双氧水 、 sodium iodide 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 丙酮 为溶剂， 反应 63.5h， 生成 (R_S)-2-phenylpropyl-2-sulfinamide
  参考文献：
  名称：

  [EN] CHIRAL 2-ARYLPROPYL-2-SULFINAMIDE AND CHIRAL N-2-ARYLPROPYL-2-SULFINYLIMINES AND SYNTHESIS THEREOF
  [FR] COMPOSÉS CHIRAUX DE 2-ARYLPROPYL-2-SULFINAMIDE ET DE N-2-ARYLPROPYL-2-SULFINYLIMINES ET LEURS PROCÉDÉS DE SYNTHÈSE

  摘要：

  本文提供了新型手性亚磺酰胺和亚胺化合物。本文还提供了合成新型手性亚磺酰胺和亚胺化合物的方法，与以往方法相比，这些方法具有简化的纯化方法。这些新型手性亚磺酰胺和亚胺化合物可用于合成复杂的天然产物和重要的药物化合物。

  公开号：

  WO2014070215A1

文献信息

• [EN] CHIRAL 2-ARYLPROPYL-2-SULFINAMIDE AND CHIRAL N-2-ARYLPROPYL-2-SULFINYLIMINES AND SYNTHESIS THEREOF<br/>[FR] COMPOSÉS CHIRAUX DE 2-ARYLPROPYL-2-SULFINAMIDE ET DE N-2-ARYLPROPYL-2-SULFINYLIMINES ET LEURS PROCÉDÉS DE SYNTHÈSE
  申请人：UNIV NANJING

  公开号：WO2014070215A1

  公开（公告）日：2014-05-08

  Provided herein are novel chiral sulfinamide and imine compounds. Also provided herein are methods of synthesizing novel chiral sulfinamide and imine compounds comprising simplified purification methods when compared to prior methods. The novel chiral sulfinamide and imine compounds are useful, for example, in the synthesis of complex natural products and pharmaceutical important compounds.

  本文提供了新型手性亚磺酰胺和亚胺化合物。本文还提供了合成新型手性亚磺酰胺和亚胺化合物的方法，与以往方法相比，这些方法具有简化的纯化方法。这些新型手性亚磺酰胺和亚胺化合物可用于合成复杂的天然产物和重要的药物化合物。
• CHIRAL 2-ARYLPROPYL-2-SULFINAMIDE AND CHIRAL N-2-ARYLPROPYL-2-SULFINYLIMINES AND SYNTHESIS THEREOF
  申请人：NANJING UNIVERSITY

  公开号：US20150274654A1

  公开（公告）日：2015-10-01

  Provided herein are novel chiral sulfinamide and imine compounds. Also provided herein are methods of synthesizing novel chiral sulfinamide and imine compounds comprising simplified purification methods when compared to prior methods. The novel chiral sulfinamide and imine compounds are useful, for example, in the synthesis of complex natural products and pharmaceutical important compounds.

  本文提供了新型手性亚磺酰胺和亚胺化合物。同时还提供了一种合成新型手性亚磺酰胺和亚胺化合物的方法，与以往方法相比，具有简化的纯化方法。这些新型手性亚磺酰胺和亚胺化合物在合成复杂天然产物和重要药物化合物方面具有用途。
• US20140275582A1
  申请人：——

  公开号：US20140275582A1

  公开（公告）日：2014-09-18
• US9216953B2
  申请人：——

  公开号：US9216953B2

  公开（公告）日：2015-12-22
• Design, Synthesis, and Applications of Chiral <i>N</i>-2-Phenyl-2-propyl Sulfinyl Imines for Group-Assisted Purification (GAP) Asymmetric Synthesis
  作者：Suresh Pindi、Jianbin Wu、Guigen Li

  DOI：10.1021/jo400354r

  日期：2013.4.19

  A new chiral (Rs)-2-phenyl-2-propyl sulfinamide has been designed and synthesized; its derived aldimines and ketimines have been applied for asymmetric addition reaction with allylmagnesium bromide. The reaction was conveniently performed at room temperature to give a series of homoallylic amines in high yields (up to quant) and diastereoselectivity (up to >99% de). The pure products were obtained by relying on group-assisted purification (GAP) chemistry to avoid traditional purification methods of column chromatography or recrystallization. The conversion of disulfide to (R(s))-thiosulfinate which contains a newly generated polar group was also confirmed to be of the GAP chemistry in which washing crude product can generate pure enantiomer. The absolute stereochemistry has been determined by X-ray analysis.