methyl (R)-1-(1-((tert-butyldimethylsilyl)oxy)vinyl)-2-phenylcycloprop-2-enecarboxylate | 1313271-76-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (R)-1-(1-((tert-butyldimethylsilyl)oxy)vinyl)-2-phenylcycloprop-2-enecarboxylate
• 英文别名: methyl (1R)-1-[1-[tert-butyl(dimethyl)silyl]oxyethenyl]-2-phenylcycloprop-2-ene-1-carboxylate
• CAS: 1313271-76-9
• 化学式: C₁₉H₂₆O₃Si
• 分子量: 330.499
• InChiKey: HASZEXUNIMWXIL-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯乙炔 、 methyl 3-tert-butyldimethylsilyloxy-2-diazobut-3-enoate 在 Rh₂(R-DOSP)₄ 作用下， 以 正戊烷 为溶剂， 反应 2.0h， 以41%的产率得到methyl (S)-1-(1-((tert-butyldimethylsilyl)oxy)vinyl)-2-phenylcycloprop-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.