(S_S)-(+)-3-chloro-2-(p-tolylsulfinyl)prop-2-ene | 261900-93-0

• 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: (S_S)-(+)-3-chloro-2-(p-tolylsulfinyl)prop-2-ene
• 英文别名: (S)-3-chloro-2-(p-tolylsulfinyl)-1-propene；1-[(S)-3-chloroprop-1-en-2-ylsulfinyl]-4-methylbenzene
• CAS: 261900-93-0
• 化学式: C₁₀H₁₁ClOS
• 分子量: 214.716
• InChiKey: HXRTZASVDBOJTC-CYBMUJFWSA-N

物化性质

• 沸点：
  382.1±35.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S_S)-(+)-3-chloro-2-(p-tolylsulfinyl)prop-2-ene 在 碘化铵 、 sodium iodide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 12.0h， 生成 (1R)-4-(methylamino)-3-[(R)-(4-methylphenyl)sulfinyl]-1-pyridin-3-ylbutan-1-ol
  参考文献：
  名称：

  Studies on the diastereoselective allylation of aldehydes with enantiopure 2-sulfinylallyl building blocks

  摘要：

  A comparative study on the allylation of aldehydes with enantiopure (S-S)-2-(p-tolylsulfonyl)-prop-2-en-1-ol (S-S)-1a and the corresponding chloride (S-S)-1b under two different reaction systems is reported. In general, better yields were obtained from chloride (S-S)-1b, whereas higher diastereoinduction was observed from alcohol (S-S)-1a. The sense of diastereoinduction is the same in both systems and the stereochemistry of the major diastereomer has been determined. Moreover, the configurational stability of the sulfoxide group on the resulting sulfinyl homoallylic alcohols 3 has been proven in each reaction system. which demonstrates the efficiency of the sulfoxide group as chiral auxiliary in these allylation processes. Finally. as an example of the synthetic potential of the resulting adducts, a total synthesis of natural enantioenriched (S)-nicotine from sulfinylalcohol 3h is reported, (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00266-x
• 作为产物：
  描述：

  (S_S)-(+)-2-(p-Tolylsulfinyl)prop-2-en-1-ol 在 甲基磺酰氯 、 三乙胺 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到(S_S)-(+)-3-chloro-2-(p-tolylsulfinyl)prop-2-ene
  参考文献：
  名称：

  在环境友好的Barbier型条件下用对映体纯的2-亚磺酰基烯丙基卤化物对醛进行非对映选择性烯丙基化

  摘要：

  [反应：参见正文]在Barbier水溶液中，一种简单，有效且非对映选择性的锌促进醛与对映纯（Ss）-3-氯-2-（对甲苯基亚磺酰基）-1-丙烯[（Ss）-1]进行的烯丙基化烯丙基化反应条件描述。观察到的非对映选择性可以通过非环状反平面过渡态模型来解释。

  DOI：

  10.1021/ol991412j

文献信息

• Barbier-Type Diastereoselective Allylation of α-Amino Aldehydes with an Enantiopure 2-Sulfinylallyl Building Block
  作者：Francesc Márquez、Raúl Montoro、Amadeu Llebaria、Elena Lago、Elies Molins、Antonio Delgado

  DOI：10.1021/jo016068u

  日期：2002.1.1

  An optimized procedure for the diastereoselective allylation under aqueous Barbier conditions of a series of alpha-amino aldehydes with our new chiral building block (S(s))-3-chloro-2-(p-tolylsulfinyl)-1-propene [(S(s))-1a] to afford enantiomerically pure sulfinylamino alcohols in good yields and diastereoselectivites is reported. High levels of diastereoinduction can be achieved from alpha-amino aldehydes

  使用我们新的手性结构单元（S（s））-3-氯-2-（对甲苯基亚磺酰基）-1-丙烯[（S）在Barbier水溶液的水性Barbier条件下进行非对映选择性烯丙基化的优化程序（s））-1a]以高收率提供对映体纯的亚磺酰基氨基醇，并且据报道有非对映选择性。从与天然α-氨基酸构型相关的α-氨基醛可以实现高水平的非对映异构诱导。
• Studies on the diastereoselective allylation of aldehydes with enantiopure 2-sulfinylallyl building blocks
  作者：Francesc Márquez、Amadeu Llebaria、Antonio Delgado

  DOI：10.1016/s0957-4166(01)00266-x

  日期：2001.7

  A comparative study on the allylation of aldehydes with enantiopure (S-S)-2-(p-tolylsulfonyl)-prop-2-en-1-ol (S-S)-1a and the corresponding chloride (S-S)-1b under two different reaction systems is reported. In general, better yields were obtained from chloride (S-S)-1b, whereas higher diastereoinduction was observed from alcohol (S-S)-1a. The sense of diastereoinduction is the same in both systems and the stereochemistry of the major diastereomer has been determined. Moreover, the configurational stability of the sulfoxide group on the resulting sulfinyl homoallylic alcohols 3 has been proven in each reaction system. which demonstrates the efficiency of the sulfoxide group as chiral auxiliary in these allylation processes. Finally. as an example of the synthetic potential of the resulting adducts, a total synthesis of natural enantioenriched (S)-nicotine from sulfinylalcohol 3h is reported, (C) 2001 Elsevier Science Ltd. All rights reserved.
• Diastereoselective Allylation of Aldehydes with an Enantiopure 2-Sulfinylallyl Halide under Environmentally Friendly Barbier-Type Conditions
  作者：Francesc Márquez、Amadeu Llebaria、Antonio Delgado

  DOI：10.1021/ol991412j

  日期：2000.2.1

  [reaction: see text] A simple, efficient, and diastereoselective zinc-promoted allylation of aldehydes with enantiopure (Ss)-3-chloro-2-(p-tolylsulfinyl)-1-propene [(Ss)-1] under aqueous Barbier conditions is described. The observed diastereoselectivity can be explained via an acyclic antiperiplanar transition state model.

  [反应：参见正文]在Barbier水溶液中，一种简单，有效且非对映选择性的锌促进醛与对映纯（Ss）-3-氯-2-（对甲苯基亚磺酰基）-1-丙烯[（Ss）-1]进行的烯丙基化烯丙基化反应条件描述。观察到的非对映选择性可以通过非环状反平面过渡态模型来解释。