(R)-(-)-3-acetyl-8-methoxy-1-methyl-2,3,4,5-tetrahydro-1,4-methano-1H-3-benzazepine | 178681-66-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: (R)-(-)-3-acetyl-8-methoxy-1-methyl-2,3,4,5-tetrahydro-1,4-methano-1H-3-benzazepine
• 英文别名: 1-[(1R,9R)-4-methoxy-1-methyl-10-azatricyclo[7.2.1.02,7]dodeca-2(7),3,5-trien-10-yl]ethanone
• CAS: 178681-66-8
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: KVEAPISSFZQOSM-DOMZBBRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(-)-3-acetyl-8-methoxy-1-methyl-2,3,4,5-tetrahydro-1,4-methano-1H-3-benzazepine 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 75.0h， 生成 (1R,4R)-8-methoxy-1-methyl-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine
  参考文献：
  名称：

  Asymmetric Synthesis of Benzylic Quaternary Carbon Center via an Enzymatic Reaction

  摘要：

  (R)-(+)-((R)-(+)-12) and (S)-(-)-1-formyl-1-methyl-7-methoxy-1,2,3,4-tetrahydronaphthalene ((S)-(-)-12) were synthesized based on enantioselective PLE hydrolysis of diethyl 2-(m-methoxyphenyl)-2-methylmalonate. From (R)-(+)-12, (+)-O-Methylaphanorphine (16) and (-)-aphanorphine were synthesized. (S)-(+)-1-(N-Acetyl-N-methylaminoethyl)-1-methyl-7-methoxytetralin (25) was synthesized from (S)-(-)-12. This transformation constitutes a formal synthesis of (-)-eptazocine.

  DOI：

  10.3987/com-96-7421
• 作为产物：
  描述：

  3-甲氧基苯基乙酸乙酯 在 platinum(IV) oxide 、 palladium on activated charcoal 盐酸 、 potassium dichromate 、 sodium hydroxide 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 锂硼氢 、 高氯酸 、 Celite 、 pH 8.04 phosphate buffer 、 硫酸 、 盐酸羟胺 、 氢气 、 溴 、 sodium methylate 、 sodium acetate 、 sodium hydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 、 丙酮 、 paraffin 、 苯 为溶剂， 反应 227.83h， 生成 (R)-(-)-3-acetyl-8-methoxy-1-methyl-2,3,4,5-tetrahydro-1,4-methano-1H-3-benzazepine
  参考文献：
  名称：

  Asymmetric Synthesis of Benzylic Quaternary Carbon Center via an Enzymatic Reaction

  摘要：

  (R)-(+)-((R)-(+)-12) and (S)-(-)-1-formyl-1-methyl-7-methoxy-1,2,3,4-tetrahydronaphthalene ((S)-(-)-12) were synthesized based on enantioselective PLE hydrolysis of diethyl 2-(m-methoxyphenyl)-2-methylmalonate. From (R)-(+)-12, (+)-O-Methylaphanorphine (16) and (-)-aphanorphine were synthesized. (S)-(+)-1-(N-Acetyl-N-methylaminoethyl)-1-methyl-7-methoxytetralin (25) was synthesized from (S)-(-)-12. This transformation constitutes a formal synthesis of (-)-eptazocine.

  DOI：

  10.3987/com-96-7421

文献信息

• Asymmetric Synthesis of Benzylic Quaternary Carbon Center via an Enzymatic Reaction
  作者：Shunsaku Shiotani、Hirohiko Okada、Kumiko Nakamata、Takako Yamamoto、Fumie Sekino

  DOI：10.3987/com-96-7421

  日期：——

  (R)-(+)-((R)-(+)-12) and (S)-(-)-1-formyl-1-methyl-7-methoxy-1,2,3,4-tetrahydronaphthalene ((S)-(-)-12) were synthesized based on enantioselective PLE hydrolysis of diethyl 2-(m-methoxyphenyl)-2-methylmalonate. From (R)-(+)-12, (+)-O-Methylaphanorphine (16) and (-)-aphanorphine were synthesized. (S)-(+)-1-(N-Acetyl-N-methylaminoethyl)-1-methyl-7-methoxytetralin (25) was synthesized from (S)-(-)-12. This transformation constitutes a formal synthesis of (-)-eptazocine.