(R)-1-phenyl-2-(phenylsulfonyl)ethyl acrylate | 950478-21-4

• 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)-1-phenyl-2-(phenylsulfonyl)ethyl acrylate
• 英文别名: [(1R)-2-(benzenesulfonyl)-1-phenylethyl] prop-2-enoate
• CAS: 950478-21-4
• 化学式: C₁₇H₁₆O₄S
• 分子量: 316.378
• InChiKey: IUHKWONMMXPCPG-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-1-phenyl-2-(phenylsulfonyl)ethyl acrylate 、 (+)-(R)-1-nitro-2-phenylpropane 在 4-二甲氨基吡啶 、 二碳酸二叔丁酯 作用下， 以 乙腈 为溶剂， 反应 51.0h， 以53%的产率得到[1-phenyl-2-(phenylsulfonyl)ethyl] 3-(1-phenylethyl)-4,5-dihydroisoxazole-5-carboxylate
  参考文献：
  名称：

  Optically active nitrile oxides: synthesis and 1,3-dipolar cycloaddition reactions

  摘要：

  Baker's yeast-promoted reduction of the C=C bond in 2-aryl-1-nitropropenes gave the corresponding optically active (R)-2aryl-1-nitropropanes of high enantiomeric purity (ee > 90%). They were next converted with the aid of the Mukaiyama and Hoshino method into the optically active nitrile oxides, which were made to react in situ with ethyl propiolate, methylvinyl ketone and (R)-I-phenyl-2-(phenylsulfonyl)ethyl acrylate to yield the appropriate, enantiomerically enriched, isoxazoles or 4,5-dihydroisoxazoles as diastereomeric mixtures, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.021
• 作为产物：
  描述：

  (R)-(-)-2-氯-1-苯乙醇 在 Oxone 、 sodium hydroxide 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 (R)-1-phenyl-2-(phenylsulfonyl)ethyl acrylate
  参考文献：
  名称：

  Optically active nitrile oxides: synthesis and 1,3-dipolar cycloaddition reactions

  摘要：

  Baker's yeast-promoted reduction of the C=C bond in 2-aryl-1-nitropropenes gave the corresponding optically active (R)-2aryl-1-nitropropanes of high enantiomeric purity (ee > 90%). They were next converted with the aid of the Mukaiyama and Hoshino method into the optically active nitrile oxides, which were made to react in situ with ethyl propiolate, methylvinyl ketone and (R)-I-phenyl-2-(phenylsulfonyl)ethyl acrylate to yield the appropriate, enantiomerically enriched, isoxazoles or 4,5-dihydroisoxazoles as diastereomeric mixtures, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.021

文献信息

• Optically active nitrile oxides: synthesis and 1,3-dipolar cycloaddition reactions
  作者：Marcin Zagozda、Jan Plenkiewicz

  DOI：10.1016/j.tetasy.2007.05.021

  日期：2007.7

  Baker's yeast-promoted reduction of the C=C bond in 2-aryl-1-nitropropenes gave the corresponding optically active (R)-2aryl-1-nitropropanes of high enantiomeric purity (ee > 90%). They were next converted with the aid of the Mukaiyama and Hoshino method into the optically active nitrile oxides, which were made to react in situ with ethyl propiolate, methylvinyl ketone and (R)-I-phenyl-2-(phenylsulfonyl)ethyl acrylate to yield the appropriate, enantiomerically enriched, isoxazoles or 4,5-dihydroisoxazoles as diastereomeric mixtures, respectively. (c) 2007 Elsevier Ltd. All rights reserved.