methyl (R)-1-acetyl-2-(3-ethynylphenyl)cycloprop-2-enecarboxylate | 1313271-95-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl (R)-1-acetyl-2-(3-ethynylphenyl)cycloprop-2-enecarboxylate
• 英文别名: methyl (1R)-1-acetyl-2-(3-ethynylphenyl)cycloprop-2-ene-1-carboxylate
• CAS: 1313271-95-2
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: GTTFEQIWUHHLCG-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3-二乙炔苯 、 methyl 3-tert-butyldimethylsilyloxy-2-diazobut-3-enoate 在 Rh₂(S-PTAD)4 、 四丁基氟化铵 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以85%的产率得到methyl (R)-1-acetyl-2-(3-ethynylphenyl)cycloprop-2-enecarboxylate
  参考文献：
  名称：

  Rh2(S-PTAD)4-catalyzed asymmetric cyclopropenation of aryl alkynes

  摘要：

  Rh-2(S-PTAD)(4) is an effective catalyst for the asymmetric cyclopropenation of aryl alkynes using a siloxyvinyldiazoacetate as the carbenoid precursor. Upon deprotection of the silyl protecting group, highly enantioenriched cyclopropenes bearing geminal acceptor groups can be accessed. These cyclopropenes undergo regioselective rhodium(II)-catalyzed ring expansion to furans. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.029

文献信息

• Rh2(S-PTAD)4-catalyzed asymmetric cyclopropenation of aryl alkynes
  作者：John F. Briones、Huw M.L. Davies

  DOI：10.1016/j.tet.2011.04.029

  日期：2011.6

  Rh-2(S-PTAD)(4) is an effective catalyst for the asymmetric cyclopropenation of aryl alkynes using a siloxyvinyldiazoacetate as the carbenoid precursor. Upon deprotection of the silyl protecting group, highly enantioenriched cyclopropenes bearing geminal acceptor groups can be accessed. These cyclopropenes undergo regioselective rhodium(II)-catalyzed ring expansion to furans. (C) 2011 Elsevier Ltd. All rights reserved.