(3S,4R)-3-hydroxy-2,2,4-trimethylhex-5-enoic acid methyl ester | 639518-93-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (3S,4R)-3-hydroxy-2,2,4-trimethylhex-5-enoic acid methyl ester
• 英文别名: methyl (3S,4R)-3-hydroxy-2,2,4-trimethylhex-5-enoate
• CAS: 639518-93-7
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: JAJDJRNHTWOHOB-SFYZADRCSA-N

物化性质

• 沸点：
  255.7±28.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-hydroxy-2,2,4-trimethylhex-5-enoic acid methyl ester 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Asymmetric synthesis of (3S,4R,7S)-(−)-3-hydroxy-7-methoxy-2,2,4-trimethyl-decanoic acid, a plausible polyketide fragment of halipeptin A

  摘要：

  The first enantioselective synthesis of (3S,4R,7S)-(-)-3-hydroxy-7-methoxy-2,2,4-trimethyl-decanoic acid 4 in 11 steps and 6% overall yield, starting from commercially available methyl 2,2-dimethyl-3-hydroxy propionate 5 is described. The stereochemical flexible synthetic pathway involves a Brown's crotylboration reaction and a Corey-Bakshi-Shibata (CBS) oxazaborolidine-mediated reduction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00622-0
• 作为产物：
  描述：

  羟基三甲基乙酸甲酯 在 重铬酸吡啶 、 正丁基锂 、 4 A molecular sieve 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 22.25h， 生成 (3S,4R)-3-hydroxy-2,2,4-trimethylhex-5-enoic acid methyl ester
  参考文献：
  名称：

  Asymmetric synthesis of (3S,4R,7S)-(−)-3-hydroxy-7-methoxy-2,2,4-trimethyl-decanoic acid, a plausible polyketide fragment of halipeptin A

  摘要：

  The first enantioselective synthesis of (3S,4R,7S)-(-)-3-hydroxy-7-methoxy-2,2,4-trimethyl-decanoic acid 4 in 11 steps and 6% overall yield, starting from commercially available methyl 2,2-dimethyl-3-hydroxy propionate 5 is described. The stereochemical flexible synthetic pathway involves a Brown's crotylboration reaction and a Corey-Bakshi-Shibata (CBS) oxazaborolidine-mediated reduction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00622-0

文献信息

• Asymmetric synthesis of (3S,4R,7S)-(−)-3-hydroxy-7-methoxy-2,2,4-trimethyl-decanoic acid, a plausible polyketide fragment of halipeptin A
  作者：Carmela Della Monica、Nakia Maulucci、Francesco De Riccardis、Irene Izzo

  DOI：10.1016/s0957-4166(03)00622-0

  日期：2003.10

  The first enantioselective synthesis of (3S,4R,7S)-(-)-3-hydroxy-7-methoxy-2,2,4-trimethyl-decanoic acid 4 in 11 steps and 6% overall yield, starting from commercially available methyl 2,2-dimethyl-3-hydroxy propionate 5 is described. The stereochemical flexible synthetic pathway involves a Brown's crotylboration reaction and a Corey-Bakshi-Shibata (CBS) oxazaborolidine-mediated reduction. (C) 2003 Elsevier Ltd. All rights reserved.