(R)-methyl 2-((2-chlorophenyl)(hydroxy)methyl)acrylate | 1403959-06-7

• 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: (R)-methyl 2-((2-chlorophenyl)(hydroxy)methyl)acrylate
• 英文别名: (R)-methyl 2-[(2-chlorophenyl)(hydroxy)methyl]acrylate；methyl 2-[(S)-(2-chlorophenyl)-hydroxymethyl]prop-2-enoate
• CAS: 1403959-06-7
• 化学式: C₁₁H₁₁ClO₃
• 分子量: 226.66
• InChiKey: TXBHTSYDCBNNQN-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2-((2-chlorophenyl)(hydroxy)methyl)acrylate 在 叔丁基过氧化氢 、 甲基锂 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 以84%的产率得到
  参考文献：
  名称：

  Study of the stereoselectivity of the nucleophilic epoxidation of 3-hydroxy-2-methylene esters

  摘要：

  The diastereoselectivity of the nucleophilic epoxidation of 3-hydroxy-2-methylene esters has been studied. The 3-hydroxy-2-methylene esters were obtained through a Morita-Baylis-Hillman reaction. The resulting epoxyesters were treated with thiophenol for transformation into 2,3-dihydroxy-2-((phenylthio)methyl), which upon treatment with triphosgene afforded the corresponding cyclic carbonates. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.014
• 作为产物：
  描述：

  2-氯苯甲醛 、 丙烯酸甲酯（MA） 在 三乙烯二胺 作用下， 以 二甲基亚砜 为溶剂， 反应 96.0h， 以99%的产率得到(R)-methyl 2-((2-chlorophenyl)(hydroxy)methyl)acrylate
  参考文献：
  名称：

  Study of the stereoselectivity of the nucleophilic epoxidation of 3-hydroxy-2-methylene esters

  摘要：

  The diastereoselectivity of the nucleophilic epoxidation of 3-hydroxy-2-methylene esters has been studied. The 3-hydroxy-2-methylene esters were obtained through a Morita-Baylis-Hillman reaction. The resulting epoxyesters were treated with thiophenol for transformation into 2,3-dihydroxy-2-((phenylthio)methyl), which upon treatment with triphosgene afforded the corresponding cyclic carbonates. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.014

文献信息

• Organocatalyzed Baylis–Hillman reaction: an enantioselective approach
  作者：Prashant B. Thorat、Santosh V. Goswami、Bhimrao C. Khade、Sudhakar R. Bhusare

  DOI：10.1016/j.tetasy.2012.08.013

  日期：2012.9

  A convenient protocol has been developed for the synthesis of Baylis-Hillman adducts in the presence of a base and an organocatalyst. We have designed and synthesized organocatalysts based on hydrogen bonding using a pyrrolidine ring as the backbone and applied them to Baylis-Hillman transformations. This method provides products in good to high yields (73-90%) and with excellent enantiomeric excesses (up to 96%) and reasonable reaction times. (C) 2012 Elsevier Ltd. All rights reserved.