rac-2-(hydroxymethyl)-4-methylvaleronitrile | 83576-53-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: rac-2-(hydroxymethyl)-4-methylvaleronitrile
• 英文别名: 2-(Hydroxymethyl)-4-methylpentanenitrile
• CAS: 83576-53-8
• 化学式: C₇H₁₃NO
• 分子量: 127.186
• InChiKey: XJRRBCBGHZJOTK-UHFFFAOYSA-N

物化性质

• 沸点：
  247.8±13.0 °C(Predicted)
• 密度：
  0.937±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  rac-2-(hydroxymethyl)-4-methylvaleronitrile 在 氢氧化钾 、 氯化亚砜 作用下， 反应 12.0h， 生成 2-(羟甲基)-4-甲基戊酸甲酯
  参考文献：
  名称：

  Cysteine Derivatives as Inhibitors for Carboxypeptidase A:  Synthesis and Structure−Activity Relationships

  摘要：

  A series of cysteine (Cys) derivatives having an alkyl or arylalkyl moiety on the a-amino group of the amino acid have been synthesized as a novel type of inhibitor for carboxypeptidase A. These compounds are readily prepared starting with Cys in an optically active form. The structure-activity relationship study revealed that the inhibitors prepared from D-Cys are much more potent than the corresponding inhibitors obtained from L-CYS, and the most potent inhibitor in the series, (S)-1j with a K-i value of 55 +/- 4 nM, is obtained by introducing a phenethyl moiety on the amino group Of D-CyS. In comparison, the most active inhibitor in the series of 2-substituted 3-mercaptopropanoic acid is found to be 20, in which the phenyl ring is linked to the mercaptocarboxylic acid at the a-position with a methylene unit. A proposal that accounts for the different structural requirement for the maximum activity between the two series of inhibitors is provided.

  DOI：

  10.1021/jm010272s
• 作为产物：
  描述：

  (E)-2-Cyano-4-methyl-pent-2-enethioic acid S-tert-butyl ester 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以84%的产率得到rac-2-(hydroxymethyl)-4-methylvaleronitrile
  参考文献：
  名称：

  有机合成中的硫醇酯。：十一。一种简便的方法来制备β-羟基丙腈和丙烯腈，氰基硫代乙酸盐作为掩盖的β-羟基丙腈碳负离子

  摘要：

  通过使用氰基硫羟乙酸酯作为β-羟基丙腈碳负离子的形式等效物，可以简化β-羟基丙腈和丙烯腈的制备。

  DOI：

  10.1016/s0040-4039(00)88582-2

文献信息

• LIU, HSING-JANG;WYNN, HLA, TETRAHEDRON LETT., 1982, 23, N 31, 3151-3154
  作者：LIU, HSING-JANG、WYNN, HLA

  DOI：——

  日期：——
• Thiol esters in organic synthesis.
  作者：Hsing-Jang Liu、Hla Wynn

  DOI：10.1016/s0040-4039(00)88582-2

  日期：1982.1

  The preparation of β-hydroxypropionitriles and acrylonitriles is facilitated by the use of cyanothiolacetate as a formal equivalent of β-hydroxypropionitrile carbanion.

  通过使用氰基硫羟乙酸酯作为β-羟基丙腈碳负离子的形式等效物，可以简化β-羟基丙腈和丙烯腈的制备。
• Cysteine Derivatives as Inhibitors for Carboxypeptidase A:  Synthesis and Structure−Activity Relationships
  作者：Jung Dae Park、Dong H. Kim

  DOI：10.1021/jm010272s

  日期：2002.2.1

  A series of cysteine (Cys) derivatives having an alkyl or arylalkyl moiety on the a-amino group of the amino acid have been synthesized as a novel type of inhibitor for carboxypeptidase A. These compounds are readily prepared starting with Cys in an optically active form. The structure-activity relationship study revealed that the inhibitors prepared from D-Cys are much more potent than the corresponding inhibitors obtained from L-CYS, and the most potent inhibitor in the series, (S)-1j with a K-i value of 55 +/- 4 nM, is obtained by introducing a phenethyl moiety on the amino group Of D-CyS. In comparison, the most active inhibitor in the series of 2-substituted 3-mercaptopropanoic acid is found to be 20, in which the phenyl ring is linked to the mercaptocarboxylic acid at the a-position with a methylene unit. A proposal that accounts for the different structural requirement for the maximum activity between the two series of inhibitors is provided.