(Z)-4-(Methylhydroxyphosphinyl)-3-cyano-2-hydroxycrotonic acid | 132119-81-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-4-(Methylhydroxyphosphinyl)-3-cyano-2-hydroxycrotonic acid
• 英文别名: 4-(Methylhydroxyphosphinyl)-3-cyano-2-hydroxycrotonic acid；(Z)-3-cyano-2-hydroxy-4-[hydroxy(methyl)phosphoryl]but-2-enoic acid
• CAS: 132119-81-4
• 化学式: C₆H₈NO₅P
• 分子量: 205.107
• InChiKey: XNXTVLYKOSPWOU-PLNGDYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-4-(Methylhydroxyphosphinyl)-3-cyano-2-hydroxycrotonic acid 生成 (4-hydroxy-2,5-dioxopyrrolidin-3-yl)methyl-methylphosphinic acid
  参考文献：
  名称：

  KAZAKOV, I. V.;ODINETS, I. L.;ANTIPIN, M. YU.;PETROVSKIJ, P. V.;KOVALENKO+, IZV. AN CCCP. CEP. XIM.,(1990) N, S. 2120-2127

  摘要：

  DOI：
• 作为产物：
  描述：

  3-[乙氧基(甲基)磷酰基]丙腈 、 草酸二乙酯 在 sodium hydroxide 、 sodium ethanolate 作用下， 生成 (Z)-4-(Methylhydroxyphosphinyl)-3-cyano-2-hydroxycrotonic acid
  参考文献：
  名称：

  Synthesis of 2-keto-4-phosphorylbutyric acids and their derivatives

  摘要：

  The Claisen condensation of 3-phosphorylated propionitriles with diethyl oxalate has been examined. The product of the condensation of 3-(methylethoxyphosphinyl)-propionitrile, following hydrolysis, has been shown to be the enol form (Z-isomer) of 4-(methylhydroxyphosphinyl)-3-cyano-2-ketoburyric acid. On crystallizaton from water, the other isomers (the E-isomer of the enol or the keto-forms) were not isolated. Distillation of the products of silylation of the reaction mixture with hexamethyldisilazane gave both geometric isomers of the enol (Z and E). In aqueous solution, the enol gradually cyclizes to give 2-hydroxy-3-(methylhydroxyphosphinyl)-citraconimide.

  DOI：

  10.1007/bf00958265

文献信息

• KAZAKOV, I. V.;ODINETS, I. L.;ANTIPIN, M. YU.;PETROVSKIJ, P. V.;KOVALENKO+, IZV. AN CCCP. CEP. XIM.,(1990) N, S. 2120-2127
  作者：KAZAKOV, I. V.、ODINETS, I. L.、ANTIPIN, M. YU.、PETROVSKIJ, P. V.、KOVALENKO+

  DOI：——

  日期：——
• Synthesis of 2-keto-4-phosphorylbutyric acids and their derivatives
  作者：P. V. Kazakov、I. L. Odinets、M. Yu. Antipin、P. V. Petrovskii、L. V. Kovalenko、Yu. T. Struchkov、T. A. Mastryukova

  DOI：10.1007/bf00958265

  日期：1990.9

  The Claisen condensation of 3-phosphorylated propionitriles with diethyl oxalate has been examined. The product of the condensation of 3-(methylethoxyphosphinyl)-propionitrile, following hydrolysis, has been shown to be the enol form (Z-isomer) of 4-(methylhydroxyphosphinyl)-3-cyano-2-ketoburyric acid. On crystallizaton from water, the other isomers (the E-isomer of the enol or the keto-forms) were not isolated. Distillation of the products of silylation of the reaction mixture with hexamethyldisilazane gave both geometric isomers of the enol (Z and E). In aqueous solution, the enol gradually cyclizes to give 2-hydroxy-3-(methylhydroxyphosphinyl)-citraconimide.