(1R*,4S*,5S*,4'S*)-7,7-dimethoxy-1,2,3,4-tetrachloro-5-<4'-(4'-methyl-2'-phenyl-2'-oxazolinyl)>-bicyclo<2.2.1>hept-2-ene | 140867-29-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R*,4S*,5S*,4'S*)-7,7-dimethoxy-1,2,3,4-tetrachloro-5-<4'-(4'-methyl-2'-phenyl-2'-oxazolinyl)>-bicyclo<2.2.1>hept-2-ene
• 英文别名: (1R*,4S*,5S*,4'R*)-7,7-dimethoxy-1,2,3,4-tetrachloro-5-<4'-(4'-methyl-2'-phenyl-2'-oxazolinyl)>-bicyclo<2.2.1>hept-2-ene；(1R*,4S*,5S*,4'R*)-7,7-dimethoxy-1,2,3,4-tetrachloro-5-[4'-(4'-methyl-2'-phenyl-2'-oxazolinyl)]-bicyclo[2.2.1]hept-2-ene
• CAS: 140867-29-4；140867-30-7
• 化学式: C₁₉H₁₉Cl₄NO₃
• 分子量: 451.177
• InChiKey: HOOFJMRNERINLU-GYIHYUDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  40.05
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R*,4S*,5S*,4'S*)-7,7-dimethoxy-1,2,3,4-tetrachloro-5-<4'-(4'-methyl-2'-phenyl-2'-oxazolinyl)>-bicyclo<2.2.1>hept-2-ene 在 硫酸 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以98%的产率得到(1R*,4S*,5S*,2'R*)-7,7-dimethoxy-1,2,3,4-tetrachloro-5-<2'-(2'-amino-1'-benzyloxy)-propyl>-bicyclo<2.2.1>hept-2-ene
  参考文献：
  名称：

  A new retro-aza-ene reaction: formal reductive amination of an α-keto acid to an α-amino acid

  摘要：

  Two diastereomeric reductive amination reagents, 1a and 1b, were synthesized. Each reagent was condensed with ethyl pyruvate as a model alpha-keto acid. Flash vacuum pyrolysis of the pyruvate adducts, 10a and 10b, results in cheleotropic elimination of CO, followed by a new type of retro-aza-ene reaction. A molecule of benzene and a protected alanine derivative, 11, are produced in the retro-ene reaction. This sequence constitutes the first formal reductive amination of an alpha-keto acid via a thermal rearrangement. Diastereomer 10b undergoes the rearrangement more readily than diastereomer 10a, indicating that an exo transition state is preferred over an endo transition state for this particular retro-aza-ene reaction.

  DOI：

  10.1016/s0040-4020(01)88730-5
• 作为产物：
  描述：

  (+/-)-N-benzoyl-α-vinylalanine methyl ester 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 79.0h， 生成 (1R*,4S*,5S*,4'S*)-7,7-dimethoxy-1,2,3,4-tetrachloro-5-<4'-(4'-methyl-2'-phenyl-2'-oxazolinyl)>-bicyclo<2.2.1>hept-2-ene
  参考文献：
  名称：

  A new retro-aza-ene reaction: formal reductive amination of an α-keto acid to an α-amino acid

  摘要：

  Two diastereomeric reductive amination reagents, 1a and 1b, were synthesized. Each reagent was condensed with ethyl pyruvate as a model alpha-keto acid. Flash vacuum pyrolysis of the pyruvate adducts, 10a and 10b, results in cheleotropic elimination of CO, followed by a new type of retro-aza-ene reaction. A molecule of benzene and a protected alanine derivative, 11, are produced in the retro-ene reaction. This sequence constitutes the first formal reductive amination of an alpha-keto acid via a thermal rearrangement. Diastereomer 10b undergoes the rearrangement more readily than diastereomer 10a, indicating that an exo transition state is preferred over an endo transition state for this particular retro-aza-ene reaction.

  DOI：

  10.1016/s0040-4020(01)88730-5