ethyl (S)-2-[hydroxy(2-nitrophenyl)methyl]acrylate | 1192469-23-0

• 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: ethyl (S)-2-[hydroxy(2-nitrophenyl)methyl]acrylate
• 英文别名: ethyl 2-[(S)-hydroxy-(2-nitrophenyl)methyl]prop-2-enoate
• CAS: 1192469-23-0
• 化学式: C₁₂H₁₃NO₅
• 分子量: 251.239
• InChiKey: BUONYSUNIFUVKX-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  邻硝基苯甲醛 、 丙烯酸乙酯 在 C₃₁H₄₇N₂PS 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 ethyl (S)-2-[hydroxy(2-nitrophenyl)methyl]acrylate 、 ethyl (R)-2-[hydroxy(2-nitrophenyl)methyl]acrylate
  参考文献：
  名称：

  手性膦硫脲催化丙烯酸酯与芳族醛的不对称Morita-Baylis-Hillman反应

  摘要：

  合成了一系列手性双官能硫代硫脲，并将其用于芳香醛与丙烯酸酯的对映选择性森田-贝利斯-希尔曼反应。在8 mol％的有机催化剂2e的存在下，在温和的反应条件下以良好的对映选择性和高达96％的产率获得了Baylis-Hillman加合物。

  DOI：

  10.1016/j.tet.2009.07.066

文献信息

• Valine-derived phosphinothiourea as organocatalyst in enantioselective Morita–Baylis–Hillman reactions of acrylates with aromatic aldehydes
  作者：Jing-Jing Gong、Kui Yuan、Xin-Yan Wu

  DOI：10.1016/j.tetasy.2009.07.047

  日期：2009.9

  A new type of chiral bifunctional phosphinothiourea derived from L-valine is synthesized and used as an organocatalyst in the enantioselective Monta-Baylis-Hillman reaction of aromatic aldehydes with acrylates. The desired products were obtained in good enantioselectivities (up to :33% ee) and in excellent yields (up to 96%) under mild reaction conditions. (C) 2009 Elsevier Ltd All rights reserved
• A New BINOL-Derived Chiral Bifunctional Phosphine Organocatalyst: Preparation and Application in Asymmetric (Aza)-Morita-Baylis-Hillman Reactions
  作者：Chunzhang Wang、Lijun Wang、San Zeng、Silong Xu、Zhengjie He

  DOI：10.1080/10426507.2012.761987

  日期：2013.11.1

  A new BINOL-derived chiral bifunctional phosphine has been designed and successfully prepared, which features a cyclic substructure of 1,3,5-diazaphosphinane. This chiral phosphine possesses good air stability in solid state, and it can be conveniently used as a relatively more nucleophilic phosphine organocatalyst. Preliminary investigations showed that it could generally afford fair to excellent yields but only modest enantioselectivity in the (aza)-Morita-Baylis-Hillman reactions of activated olefins such as ethyl acrylate and methyl vinyl ketone with aldehydes or imines. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus Sulfer and Silicon and the Related Elements for the following free supplemental files: Additional text and figures.]