(1R*,2R*,3S*,6S*,7S*,8S*)-6-amino-6-methyl-1,2,8-trichloro-3,9,9-trimethoxy-4-oxatricyclo<5.2.1.0^3,8>decane | 140867-34-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R*,2R*,3S*,6S*,7S*,8S*)-6-amino-6-methyl-1,2,8-trichloro-3,9,9-trimethoxy-4-oxatricyclo<5.2.1.0^3,8>decane
• 英文别名: (1S,2S,3R,6R,7R,8S)-1,2,8-trichloro-3,9,9-trimethoxy-6-methyl-4-oxatricyclo[5.2.1.03,8]decan-6-amine
• CAS: 140867-34-1
• 化学式: C₁₃H₂₀Cl₃NO₄
• 分子量: 360.665
• InChiKey: PSMLBWPTGALNPL-XZPZHEHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  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 氢氧化钾 、 硫酸 、 sodium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 22.5h， 生成 (1R*,2R*,3S*,6S*,7S*,8S*)-6-amino-6-methyl-1,2,8-trichloro-3,9,9-trimethoxy-4-oxatricyclo<5.2.1.0^3,8>decane
  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

文献信息

• A new retro-aza-ene reaction: formal reductive amination of an α-keto acid to an α-amino acid
  作者：David B. Berkowitz、W. Bernd Schweizer

  DOI：10.1016/s0040-4020(01)88730-5

  日期：1992.2

  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.