(S)-methyl 2-phenyl-2-(2-styryl-1,3-dioxolan-2-yl)acetate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-methyl 2-phenyl-2-(2-styryl-1,3-dioxolan-2-yl)acetate
• 英文别名: methyl (2S)-2-phenyl-2-[2-[(E)-2-phenylethenyl]-1,3-dioxolan-2-yl]acetate
• 化学式: C₂₀H₂₀O₄
• 分子量: 324.376
• InChiKey: ASVRFBIEMSMLIB-QFQMRYFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  a-叠氮基-苯乙酸甲酯 、 2-[(E)-2-phenylethenyl]-1,3-dioxolane 在 Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4 作用下， 以 various solvent(s) 为溶剂， 反应 1.0h， 生成 (R)-methyl 2-phenyl-2-(2-styryl-1,3-dioxolan-2-yl)acetate 、 (S)-methyl 2-phenyl-2-(2-styryl-1,3-dioxolan-2-yl)acetate
  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

文献信息

• Asymmetric C–H insertion of Rh(II) stabilized carbenoids into acetals: A C–H activation protocol as a Claisen condensation equivalent
  作者：Huw M.L. Davies、Jaemoon Yang、Joachim Nikolai

  DOI：10.1016/j.jorganchem.2005.08.026

  日期：2005.12

  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.