(R)-2-phenyl-2-(2-phenyl-1,3-dioxolan-2-yl)ethanol | 873527-35-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (R)-2-phenyl-2-(2-phenyl-1,3-dioxolan-2-yl)ethanol
• CAS: 873527-35-6
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: UNWNQIQAJHBLDZ-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-2-phenyl-2-(2-phenyl-1,3-dioxolan-2-yl)ethanol 在 碘 作用下， 以 丙酮 为溶剂， 以66%的产率得到(R)-3-hydroxy-1,2-diphenylpropan-1-one
  参考文献：
  名称：

  Asymmetric C–H insertion of Rh(II) stabilized carbenoids into acetals: A C–H activation protocol as a Claisen condensation equivalent

  摘要：

  The dirhodium tetraprolinate, Rh-2(S-DOSP)(4) is an efficient catalyst in an enantio selective C-H activation protocol. Rh-2(S-DOSP)(4) catalyzed decomposition of aryldiazoacetates or vinyldiazoacetates results in the formation of transient rhodium carbenoid intermediates. These inter-mediates are capable of selectively inserting into the C-H bond of acetals. The resulting products are protected P-keto esters, and so the C-H activation protocol can be considered as strategically equivalent to the Claisen condensation. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.08.026
• 作为产物：
  描述：

  2-苯基-1,3-二四氢呋喃 、 a-叠氮基-苯乙酸甲酯 在 Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2-phenyl-2-(2-phenyl-1,3-dioxolan-4-yl)ethanol 、 (S)-2-phenyl-2-(2-phenyl-1,3-dioxolan-2-yl)ethanol 、 (R)-2-phenyl-2-(2-phenyl-1,3-dioxolan-2-yl)ethanol
  参考文献：
  名称：

  Asymmetric C–H insertion of Rh(II) stabilized carbenoids into acetals: A C–H activation protocol as a Claisen condensation equivalent

  摘要：

  The dirhodium tetraprolinate, Rh-2(S-DOSP)(4) is an efficient catalyst in an enantio selective C-H activation protocol. Rh-2(S-DOSP)(4) catalyzed decomposition of aryldiazoacetates or vinyldiazoacetates results in the formation of transient rhodium carbenoid intermediates. These inter-mediates are capable of selectively inserting into the C-H bond of acetals. The resulting products are protected P-keto esters, and so the C-H activation protocol can be considered as strategically equivalent to the Claisen condensation. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.08.026