benzyl 4,4-dimethyl-5-oxo-5-phenyl-pent-2-enoate | 756491-90-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 4,4-dimethyl-5-oxo-5-phenyl-pent-2-enoate
• 英文别名: benzyl (E)-4,4-dimethyl-5-oxo-5-phenylpent-2-enoate
• CAS: 756491-90-4
• 化学式: C₂₀H₂₀O₃
• 分子量: 308.377
• InChiKey: LEIXOOQCNWPQEN-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 4,4-dimethyl-5-oxo-5-phenyl-pent-2-enoate 在 samarium diiodide 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 以85%的产率得到((1R,2R)-2-Hydroxy-3,3-dimethyl-2-phenyl-cyclopropyl)-acetic acid benzyl ester
  参考文献：
  名称：

  SmI2-Mediated 3-exo-trig cyclisation of δ-oxo-α,β-unsaturated esters to cyclopropanols and derivatives

  摘要：

  In the presence of samarium diiodide and a proton source, delta-oxo-gamma,gamma-disubstituted-alpha,beta-unsaturated esters of general formula R-CO-C(R',R')-CH=CH-CO2Bn readily cyclise to trans-cyclopropanol products and/or lactones derived from the cis isomers. For R=aryl, good stereoselectivities (ca 90%) in favor of the alcohols are generally obtained while a mixture of alcohols and lactones is obtained with R=alkyl or H. For R=cyclopropyl, the lactone is exclusively obtained in more than 90% yield. A mechanistic rationalisation of these variations of diastereoselectivity is proposed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.074
• 作为产物：
  描述：

  2,2-二甲基-3-氧代-3-苯丙醛 、 二甲基膦乙酸苄酯 以77%的产率得到benzyl 4,4-dimethyl-5-oxo-5-phenyl-pent-2-enoate
  参考文献：
  名称：

  SmI2-Mediated 3-exo-trig cyclisation of δ-oxo-α,β-unsaturated esters to cyclopropanols and derivatives

  摘要：

  In the presence of samarium diiodide and a proton source, delta-oxo-gamma,gamma-disubstituted-alpha,beta-unsaturated esters of general formula R-CO-C(R',R')-CH=CH-CO2Bn readily cyclise to trans-cyclopropanol products and/or lactones derived from the cis isomers. For R=aryl, good stereoselectivities (ca 90%) in favor of the alcohols are generally obtained while a mixture of alcohols and lactones is obtained with R=alkyl or H. For R=cyclopropyl, the lactone is exclusively obtained in more than 90% yield. A mechanistic rationalisation of these variations of diastereoselectivity is proposed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.074