(S)-1-methoxy-2-(3,3-dimethyl-1-butynylthio)-1-phenylethane | 649885-18-7

• 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)-1-methoxy-2-(3,3-dimethyl-1-butynylthio)-1-phenylethane
• 英文别名: {(1S)-2-[(3,3-Dimethylbut-1-yn-1-yl)sulfanyl]-1-methoxyethyl}benzene；[(1S)-2-(3,3-dimethylbut-1-ynylsulfanyl)-1-methoxyethyl]benzene
• CAS: 649885-18-7
• 化学式: C₁₅H₂₀OS
• 分子量: 248.389
• InChiKey: PHUKLYWBPMQHSZ-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-methoxy-2-(3,3-dimethyl-1-butynylthio)-1-phenylethane 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex diethylzinc 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 methyl (E)-4-benzyloxy-3-[(1S)-(2-methoxy-2-phenylethyl)sulfinyl]-2-butenoate
  参考文献：
  名称：

  Synthesis of chiral vinylic sulfoxides by Pd-catalyzed asymmetric sulfinylzincation

  摘要：

  Novel asymmetric sulfinylzincation of alkynoates has been accomplished via a Pd-catalyzed sulfinylzincation using 1-alkynyl sulfoxides bearing chiral auxiliaries as a sulfinylating reagent. The reaction proceeded in a highly syn-selective fashion, giving the (E)-beta-sulfinyl alpha,beta-unsaturated ester exclusively. Among the chiral sulfinylating reagents tested, an isoborneol-type compound (Rs)-4 showed the best results in terms of both yield and diastereoselectivity. As a result of optimization of the reaction, the selectivity was improved up to 92:8 dr, and stereochemistry of the newly formed sulfur stereogenic center was revealed as (Ss)-configuration. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.037
• 作为产物：
  描述：

  (S)-2-mercapto-1-phenylethanol 在 六甲基磷酰三胺 、 正丁基锂 、 sodium iodate 、 sodium hydride 、 氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (S)-1-methoxy-2-(3,3-dimethyl-1-butynylthio)-1-phenylethane
  参考文献：
  名称：

  Synthesis of chiral vinylic sulfoxides by Pd-catalyzed asymmetric sulfinylzincation

  摘要：

  Novel asymmetric sulfinylzincation of alkynoates has been accomplished via a Pd-catalyzed sulfinylzincation using 1-alkynyl sulfoxides bearing chiral auxiliaries as a sulfinylating reagent. The reaction proceeded in a highly syn-selective fashion, giving the (E)-beta-sulfinyl alpha,beta-unsaturated ester exclusively. Among the chiral sulfinylating reagents tested, an isoborneol-type compound (Rs)-4 showed the best results in terms of both yield and diastereoselectivity. As a result of optimization of the reaction, the selectivity was improved up to 92:8 dr, and stereochemistry of the newly formed sulfur stereogenic center was revealed as (Ss)-configuration. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.037

文献信息

• Synthesis of chiral vinylic sulfoxides by Pd-catalyzed asymmetric sulfinylzincation
  作者：Naoyoshi Maezaki、Suguru Yagi、Shizuka Ohsawa、Hirofumi Ohishi、Tetsuaki Tanaka

  DOI：10.1016/j.tet.2003.10.037

  日期：2003.12

  Novel asymmetric sulfinylzincation of alkynoates has been accomplished via a Pd-catalyzed sulfinylzincation using 1-alkynyl sulfoxides bearing chiral auxiliaries as a sulfinylating reagent. The reaction proceeded in a highly syn-selective fashion, giving the (E)-beta-sulfinyl alpha,beta-unsaturated ester exclusively. Among the chiral sulfinylating reagents tested, an isoborneol-type compound (Rs)-4 showed the best results in terms of both yield and diastereoselectivity. As a result of optimization of the reaction, the selectivity was improved up to 92:8 dr, and stereochemistry of the newly formed sulfur stereogenic center was revealed as (Ss)-configuration. (C) 2003 Elsevier Ltd. All rights reserved.