(S)-3-羟基十四烷腈 | 958221-98-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (S)-3-羟基十四烷腈
• 英文名称: (3S)-3-hydroxytetradecanenitrile
• CAS: 958221-98-2
• 化学式: C₁₄H₂₇NO
• 分子量: 225.374
• InChiKey: ILNUGZHDTJANGX-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  (S)-3-羟基十四烷腈 在 sodium hydroxide 、 双氧水 、 三乙胺 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 29.5h， 生成
  参考文献：
  名称：

  A practical enantioselective synthesis of (S)-3-hydroxytetradecanoic acid

  摘要：

  (S)-3-Hydroxytetradecanoic acid 1 has been synthesized in an overall yield of 27% from (S)-epichlorohydrin 2 as follows: (1) regio and chemoselective epoxide opening of 2 with a Grignard reagent under the catalysis by Cu(I) followed by consecutive epoxide formation; (2) regioselective epoxide opening of (S)1,2-epoxytridecane 4 with cyanide anion under pH controlled conditions followed by consecutive nitrile hydrolysis with alkaline H2O2 gave crude 1; (3) its purification via the N,N-dicyclohexylammonium salt 6. The method thus devised is practical and scalable for the industrial production of 1. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00290-6
• 作为产物：
  描述：

  (S)-1-氯-2-十三醇 在 sodium hydroxide 、 硫酸 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 6.3h， 生成 (S)-3-羟基十四烷腈
  参考文献：
  名称：

  A practical enantioselective synthesis of (S)-3-hydroxytetradecanoic acid

  摘要：

  (S)-3-Hydroxytetradecanoic acid 1 has been synthesized in an overall yield of 27% from (S)-epichlorohydrin 2 as follows: (1) regio and chemoselective epoxide opening of 2 with a Grignard reagent under the catalysis by Cu(I) followed by consecutive epoxide formation; (2) regioselective epoxide opening of (S)1,2-epoxytridecane 4 with cyanide anion under pH controlled conditions followed by consecutive nitrile hydrolysis with alkaline H2O2 gave crude 1; (3) its purification via the N,N-dicyclohexylammonium salt 6. The method thus devised is practical and scalable for the industrial production of 1. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00290-6

文献信息

• A practical enantioselective synthesis of (S)-3-hydroxytetradecanoic acid
  作者：Keisuke Matsuyama、Masaya Ikunaka

  DOI：10.1016/s0957-4166(99)00290-6

  日期：1999.7

  (S)-3-Hydroxytetradecanoic acid 1 has been synthesized in an overall yield of 27% from (S)-epichlorohydrin 2 as follows: (1) regio and chemoselective epoxide opening of 2 with a Grignard reagent under the catalysis by Cu(I) followed by consecutive epoxide formation; (2) regioselective epoxide opening of (S)1,2-epoxytridecane 4 with cyanide anion under pH controlled conditions followed by consecutive nitrile hydrolysis with alkaline H2O2 gave crude 1; (3) its purification via the N,N-dicyclohexylammonium salt 6. The method thus devised is practical and scalable for the industrial production of 1. (C) 1999 Elsevier Science Ltd. All rights reserved.