methyl 3R,S-hydroxy-3-methylheptanoate

• 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: methyl 3R,S-hydroxy-3-methylheptanoate
• 英文别名: methyl 3-hydroxy-3-methylheptanoate
• 化学式: C₉H₁₈O₃
• 分子量: 174.24
• InChiKey: PWXQBPOOQWEHHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-己酮 、 溴乙酸甲酯 在 五羰基铁 、 三氯溴甲烷 作用下， 以 氯苯 为溶剂， 反应 2.0h， 以31%的产率得到methyl 3R,S-hydroxy-3-methylheptanoate
  参考文献：
  名称：

  在 Fe(CO)5 存在下将卤代乙酸酯加成到醛和酮中

  摘要：

  使用形成络合物的溶剂和改变反应温度使得在五羰基铁促进下将卤代乙酸酯加成到醛和酮中制备 α-卤代 β-羟基羧酸酯成为可能。

  DOI：

  10.1007/bf02495489

文献信息

• A gas-liquid chromatographic method for steric analysis of 2-hydroxy, 3-hydroxy, and 2,3-dihydroxy acids
  作者：Lian-Ying Zhang、Mats Hamberg

  DOI：10.1016/0009-3084(94)90056-6

  日期：1994.12

  A method was developed for assignment of the absolute configuration of oxylipin-derived 2-hydroxy acids, 3-hydroxy acids and 2,3-dihydroxy acids. The monohydroxy acids were converted into diastereomeric N-(propionoxyacyl)-L-phenylalanine-methyl ester (PAP) derivatives by coupling to the methyl ester of L-phenylalanine followed by propionylation, whereas the 2,3-dihydroxy acids were derivatized by treatment with L-phenylalanine methyl ester followed by acetone and perchloric acid, to afford diastereomeric N-(2,3-isopropylidenedioxyacyl)-L-phenyl methyl ester (IAP) derivatives. The PAP and IAP derivatives were readily resolved by capillary gas-liquid chromatography. In addition, the method described allowed steric analysis of 3-hydroxy-3-methylheptanoic acid, a branched chain hydroxy acid derived from the prostaglandin analogue, misoprostol.
• Addition of halogenoacetic esters to aldehydes and ketones in the presence of Fe(CO)5
  作者：A. B. Terentiev、T. T. Vasilieva、N. A. Kuz'mina、O. V. Chakhovskaya、E. S. Brodsky、Yu. N. Belokon'

  DOI：10.1007/bf02495489

  日期：2000.4

  The use of complex-forming solvents and variations in the reaction temperature made it possible to prepare α-halogeno β-hydroxy carboxylic esters upon addition of halogenoacetic esters to aldehydes and ketones promoted by iron pentacarbonyl.

  使用形成络合物的溶剂和改变反应温度使得在五羰基铁促进下将卤代乙酸酯加成到醛和酮中制备 α-卤代 β-羟基羧酸酯成为可能。