2-{[hydroxy(phenyl)phosphinoyl]methyl}-4-phenylpent-4-enoic acid | 1191126-46-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-{[hydroxy(phenyl)phosphinoyl]methyl}-4-phenylpent-4-enoic acid
• 英文别名: 2-[[Hydroxy(phenyl)phosphoryl]methyl]-3-phenylpent-4-enoic acid
• CAS: 1191126-46-1
• 化学式: C₁₈H₁₉O₄P
• 分子量: 330.32
• InChiKey: MLGPNDQFJRFYOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯膦酸 、 cinnamyl acrylate 在 三甲基氯硅烷 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到2-{[hydroxy(phenyl)phosphinoyl]methyl}-4-phenylpent-4-enoic acid
  参考文献：
  名称：

  A Modular Rearrangement Approach toward Medicinally Relevant Phosphinic Structures

  摘要：

  An unprecedented coupling of a P-C and a C-C bond-forming event in a practical operation was developed to access medicinally relevant phosphinic structures. The strategy relies on an Ireland-Claisen rearrangement triggered by the phospha-Michael addition of silyl phosphonites to allyl acrylates. This protocol was extended to a more versatile three-component variant that utilizes phosphinic acids, acryloyl chlorides, and allylic alcohols as starting materials.

  DOI：

  10.1021/ol902004p

文献信息

• A Modular Rearrangement Approach toward Medicinally Relevant Phosphinic Structures
  作者：Vassilis Rogakos、Dimitris Georgiadis、Vincent Dive、Athanasios Yiotakis

  DOI：10.1021/ol902004p

  日期：2009.10.15

  An unprecedented coupling of a P-C and a C-C bond-forming event in a practical operation was developed to access medicinally relevant phosphinic structures. The strategy relies on an Ireland-Claisen rearrangement triggered by the phospha-Michael addition of silyl phosphonites to allyl acrylates. This protocol was extended to a more versatile three-component variant that utilizes phosphinic acids, acryloyl chlorides, and allylic alcohols as starting materials.