(E)-1-chloro-3-undecen-2-ol

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (E)-1-chloro-3-undecen-2-ol
• 英文别名: (E)-1-chloroundec-3-en-2-ol
• 化学式: C₁₁H₂₁ClO
• 分子量: 204.74
• InChiKey: CSCWXEXXCYBPAW-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  (E)-1-chloro-3-undecen-2-ol 在 sodium hydride 作用下， 以 二甲基亚砜 、 甲苯 、 mineral oil 为溶剂， 生成 (E)-S-(1-hydroxyundec-3-en-2-yl) O,O-diethyl phosphorodithioate
  参考文献：
  名称：

  Mild stereoselective formation of tri- and tetrasubstituted olefins by regioselective ring opening of 1,1-disubstituted vinyl oxiranes with dialkyl dithiophosphates

  摘要：

  Presented in this Letter is a mild new method to stereoselectively ring open 1,1-disubstituted vinyl oxiranes using dialkyl dithiophosphate nucleophiles. This new reaction proceeds in toluene at room temperature to afford tri- and tetrasubstituted allylic alcohols with high Z-selectivity. The syn relationship between the alcohol and the newly incorporated dithiophosphate moiety presented an opportunity to evaluate the anionic hopping properties of the ring opening product. Treatment of the ring opening product with base results in a facile phosphate hopping followed by a selective thiolate 3-exo-trig instead of a 5-exo-tet cyclization. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.028
• 作为产物：
  描述：

  反式-2-癸烯醛 、 氯碘甲烷 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.37h， 生成 (E)-1-chloro-3-undecen-2-ol
  参考文献：
  名称：

  Mild stereoselective formation of tri- and tetrasubstituted olefins by regioselective ring opening of 1,1-disubstituted vinyl oxiranes with dialkyl dithiophosphates

  摘要：

  Presented in this Letter is a mild new method to stereoselectively ring open 1,1-disubstituted vinyl oxiranes using dialkyl dithiophosphate nucleophiles. This new reaction proceeds in toluene at room temperature to afford tri- and tetrasubstituted allylic alcohols with high Z-selectivity. The syn relationship between the alcohol and the newly incorporated dithiophosphate moiety presented an opportunity to evaluate the anionic hopping properties of the ring opening product. Treatment of the ring opening product with base results in a facile phosphate hopping followed by a selective thiolate 3-exo-trig instead of a 5-exo-tet cyclization. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.028

文献信息

• Mild stereoselective formation of tri- and tetrasubstituted olefins by regioselective ring opening of 1,1-disubstituted vinyl oxiranes with dialkyl dithiophosphates
  作者：Boying Guo、Edon Vitaku、Jon T. Njardarson

  DOI：10.1016/j.tetlet.2014.04.028

  日期：2014.5

  Presented in this Letter is a mild new method to stereoselectively ring open 1,1-disubstituted vinyl oxiranes using dialkyl dithiophosphate nucleophiles. This new reaction proceeds in toluene at room temperature to afford tri- and tetrasubstituted allylic alcohols with high Z-selectivity. The syn relationship between the alcohol and the newly incorporated dithiophosphate moiety presented an opportunity to evaluate the anionic hopping properties of the ring opening product. Treatment of the ring opening product with base results in a facile phosphate hopping followed by a selective thiolate 3-exo-trig instead of a 5-exo-tet cyclization. (C) 2014 Elsevier Ltd. All rights reserved.