tert-butyl (Z)-2-diazo-5-phenylpent-4-enoate | 1443128-97-9

• 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: tert-butyl (Z)-2-diazo-5-phenylpent-4-enoate
• CAS: 1443128-97-9
• 化学式: C₁₅H₁₈N₂O₂
• 分子量: 258.32
• InChiKey: SNOFYTUYXNAKQW-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.7
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (Z)-2-diazo-5-phenylpent-4-enoate 在 copper(I) bromide dimethylsulfide complex 、 三丁基膦 、 tetrakis[μ-(αS)-α-(1,1-dimethylethyl)-2,3-dihydro-1H-naphtho[1,8-cd]pyridine-2-acetato-κO:.kappaO']dirhodium(II)(Rh-Rh) 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-allyl-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
• 作为产物：
  描述：

  在 4-乙酰氨基苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以31%的产率得到tert-butyl (Z)-2-diazo-5-phenylpent-4-enoate
  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