(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 | 140867-31-8

• 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: (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
• 英文别名: (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
• CAS: 140867-31-8；140867-32-9
• 化学式: C₁₉H₂₁Cl₄NO₄
• 分子量: 469.192
• InChiKey: CTDSRNQZVPXAPW-GYIHYUDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  70.78
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (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 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以79%的产率得到(1R*,4S*,5S*,2'R*)-7,7-dimethoxy-1,2,3,4-tetrachloro-5-<2'-(2'-amino-1'-hydroxy)-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 、 硫酸 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 83.0h， 生成 (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