methyl (2S,3S)-2-bromo-3-hydroxydodecanoate | 404566-02-5

• 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: methyl (2S,3S)-2-bromo-3-hydroxydodecanoate
• CAS: 404566-02-5
• 化学式: C₁₃H₂₅BrO₃
• 分子量: 309.244
• InChiKey: YBYUGABHHBQJRH-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  methyl (2S,3S)-2-bromo-3-hydroxydodecanoate 在 sodium hexamethyldisilazane 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 4.0h， 生成 (6Z,9Z,11S,12S)-11,12-epoxyhenicosa-6,9-diene
  参考文献：
  名称：

  Synthesis of Posticlure [(6Z,9Z,11S,12S)-11,12-Epoxyhenicosa-6,9-diene], the Female Sex Pheromone of Orgyia postica

  摘要：

  Starting from commercially available (E)-2-dodecenoic acid, posticlure [(6Z,9Z,11S,12S)-11,12-epoxyhenicosa-6,9-diene (1)], the female sex pheromone of the tussock moth (Orgyia postica), was synthesized in 25% overall yield (6 steps) by employing Sharpless asymmetric dihydroxylation as the key step. Its (11R,12R)-isomer as well as its racemate were also synthesized.

  DOI：

  10.1002/1099-0690(200112)2001:24<4635::aid-ejoc4635>3.0.co;2-j
• 作为产物：
  描述：

  methyl (E)-2-dodecenoate 在 AD-mix-α 、 甲基磺酰胺 、 氢溴酸 作用下， 以 水 、 溶剂黄146 、 叔丁醇 为溶剂， 反应 1.0h， 生成 methyl (2S,3S)-2-bromo-3-hydroxydodecanoate
  参考文献：
  名称：

  Synthesis of Posticlure [(6Z,9Z,11S,12S)-11,12-Epoxyhenicosa-6,9-diene], the Female Sex Pheromone of Orgyia postica

  摘要：

  Starting from commercially available (E)-2-dodecenoic acid, posticlure [(6Z,9Z,11S,12S)-11,12-epoxyhenicosa-6,9-diene (1)], the female sex pheromone of the tussock moth (Orgyia postica), was synthesized in 25% overall yield (6 steps) by employing Sharpless asymmetric dihydroxylation as the key step. Its (11R,12R)-isomer as well as its racemate were also synthesized.

  DOI：

  10.1002/1099-0690(200112)2001:24<4635::aid-ejoc4635>3.0.co;2-j

文献信息

• Synthesis of Posticlure [(6Z,9Z,11S,12S)-11,12-Epoxyhenicosa-6,9-diene], the Female Sex Pheromone of Orgyia postica
  作者：Shin-etsu Muto、Kenji Mori

  DOI：10.1002/1099-0690(200112)2001:24<4635::aid-ejoc4635>3.0.co;2-j

  日期：2001.12

  Starting from commercially available (E)-2-dodecenoic acid, posticlure [(6Z,9Z,11S,12S)-11,12-epoxyhenicosa-6,9-diene (1)], the female sex pheromone of the tussock moth (Orgyia postica), was synthesized in 25% overall yield (6 steps) by employing Sharpless asymmetric dihydroxylation as the key step. Its (11R,12R)-isomer as well as its racemate were also synthesized.