(Z)-S-(1-hydroxy-2-methylnon-2-en-4-yl) O,O-diethyl phosphorodithioate | 1610376-77-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机二硫代磷酸及其衍生物
• 英文名称: (Z)-S-(1-hydroxy-2-methylnon-2-en-4-yl) O,O-diethyl phosphorodithioate
• 英文别名: (Z)-4-diethoxyphosphinothioylsulfanyl-2-methylnon-2-en-1-ol
• CAS: 1610376-77-6
• 化学式: C₁₄H₂₉O₃PS₂
• 分子量: 340.488
• InChiKey: HIUQUBPDMZWPSH-QBFSEMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  96.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-S-(1-hydroxy-2-methylnon-2-en-4-yl) O,O-diethyl phosphorodithioate 以 氯仿 为溶剂， 生成 (E)-S-(1-hydroxy-2-methylnon-2-en-4-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：

  (E)-S-(1-hydroxy-2-methylnon-2-en-4-yl) O,O-diethyl phosphorodithioate 以 氯仿 为溶剂， 生成 (Z)-S-(1-hydroxy-2-methylnon-2-en-4-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

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.