1-chloro-2-(chloromethyl)-3-methylbut-3-en-2-ol | 729592-76-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-chloro-2-(chloromethyl)-3-methylbut-3-en-2-ol
• CAS: 729592-76-1
• 化学式: C₆H₁₀Cl₂O
• mdl: MFCD19236223
• 分子量: 169.051
• InChiKey: KHFGAGGCHZWVJM-UHFFFAOYSA-N

物化性质

• 沸点：
  238.1±35.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-chloro-2-(chloromethyl)-3-methylbut-3-en-2-ol 在 sodium hydroxide 、 porcine pancreatic lipase 作用下， 反应 71.0h， 生成 (S)-2-hydroxy-2-(hydroxymethyl)-3-methylbut-3-enyl acetate
  参考文献：
  名称：

  Chemoenzymatic formal synthesis of (S)-(−)-phosphonotrixin

  摘要：

  Phosphonotrixin is a herbicidal antibiotic characterized by a unique structure bearing a C-P bond on an isoprene unit. The formal enantioselective synthesis of (S)-(-)-phosphonotrixin (ee = 93%) in nine steps and 12% overall yield from 1,3-dihydroxyacetone or in eight steps and 11% overall yield from 1,3-dichloroacetone is reported. The key reaction is the enzymatic desymmetrization of 2-isopropenylpropane-1,2,3-triol. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.046
• 作为产物：
  描述：

  异丙烯基溴化镁 、 1,3-二氯丙酮 以 四氢呋喃 为溶剂， 反应 0.75h， 以84%的产率得到1-chloro-2-(chloromethyl)-3-methylbut-3-en-2-ol
  参考文献：
  名称：

  Chemoenzymatic formal synthesis of (S)-(−)-phosphonotrixin

  摘要：

  Phosphonotrixin is a herbicidal antibiotic characterized by a unique structure bearing a C-P bond on an isoprene unit. The formal enantioselective synthesis of (S)-(-)-phosphonotrixin (ee = 93%) in nine steps and 12% overall yield from 1,3-dihydroxyacetone or in eight steps and 11% overall yield from 1,3-dichloroacetone is reported. The key reaction is the enzymatic desymmetrization of 2-isopropenylpropane-1,2,3-triol. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.046

文献信息

• Chemoenzymatic formal synthesis of (S)-(−)-phosphonotrixin
  作者：Robert Chênevert、Mathieu Simard、Jérôme Bergeron、Mohammed Dasser

  DOI：10.1016/j.tetasy.2004.04.046

  日期：2004.6

  Phosphonotrixin is a herbicidal antibiotic characterized by a unique structure bearing a C-P bond on an isoprene unit. The formal enantioselective synthesis of (S)-(-)-phosphonotrixin (ee = 93%) in nine steps and 12% overall yield from 1,3-dihydroxyacetone or in eight steps and 11% overall yield from 1,3-dichloroacetone is reported. The key reaction is the enzymatic desymmetrization of 2-isopropenylpropane-1,2,3-triol. (C) 2004 Elsevier Ltd. All rights reserved.