tert-butyl (1R,2S,3S)-1-benzyl-3-methyl-2-phenylcyclobutane-1-carboxylate | 1443129-14-3

• 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: tert-butyl (1R,2S,3S)-1-benzyl-3-methyl-2-phenylcyclobutane-1-carboxylate
• CAS: 1443129-14-3
• 化学式: C₂₃H₂₈O₂
• 分子量: 336.474
• InChiKey: LAOIDQPXCALQSP-KPDCDPCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  tert-butyl (E)-2-diazo-5-(phenyl)pent-4-enoate 在 copper(I) bromide dimethylsulfide complex 、 dirhodium(II) tetrakis[(S)-N-phthaloyl-tert-leucinate] 、 三丁基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 生成 tert-butyl (1R,2S,3S)-1-benzyl-3-methyl-2-phenylcyclobutane-1-carboxylate
  参考文献：
  名称：

  Enantioselective Synthesis of Cyclobutanes via Sequential Rh-catalyzed Bicyclobutanation/Cu-catalyzed Homoconjugate Addition

  摘要：

  Enantiomerically enriched cyclobutanes are constructed by a three-component process in which t-butyl (E)-2-diazo-5-arylpent-4-enoates are treated with Rh2(S-NTTL)(4) to provide enantiomerically enriched bicyclobutanes, which can subsequently engage in homoconjugate addition/enolate trapping sequence to give densely functionalized cyclobutanes with high diastereoselectivity. This three-component, two-catalyst procedure can be carried out in a single flask. Rh-2(S-NTTL)(4)-catalyzed reaction of t-butyl (Z)-2-diazo-5-phenylpent-4-enoate gives the Buchner cyclization product in excellent enantioselectivity.

  DOI：

  10.1021/ja403811t

文献信息

• Enantioselective Synthesis of Cyclobutanes via Sequential Rh-catalyzed Bicyclobutanation/Cu-catalyzed Homoconjugate Addition
  作者：Robert Panish、Srinivasa R. Chintala、David T. Boruta、Yinzhi Fang、Michael T. Taylor、Joseph M. Fox

  DOI：10.1021/ja403811t

  日期：2013.6.26

  Enantiomerically enriched cyclobutanes are constructed by a three-component process in which t-butyl (E)-2-diazo-5-arylpent-4-enoates are treated with Rh2(S-NTTL)(4) to provide enantiomerically enriched bicyclobutanes, which can subsequently engage in homoconjugate addition/enolate trapping sequence to give densely functionalized cyclobutanes with high diastereoselectivity. This three-component, two-catalyst procedure can be carried out in a single flask. Rh-2(S-NTTL)(4)-catalyzed reaction of t-butyl (Z)-2-diazo-5-phenylpent-4-enoate gives the Buchner cyclization product in excellent enantioselectivity.