(S)-(-)-6-methoxy-4-methyl-4-pivaloyloxy-3,4-dihydronaphthalen-1(2H)-one | 178681-72-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (S)-(-)-6-methoxy-4-methyl-4-pivaloyloxy-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: [(1S)-7-methoxy-1-methyl-4-oxo-2,3-dihydronaphthalen-1-yl]methyl 2,2-dimethylpropanoate
• CAS: 178681-72-6
• 化学式: C₁₈H₂₄O₄
• 分子量: 304.386
• InChiKey: SPFSXFXOAZSPSP-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(-)-6-methoxy-4-methyl-4-pivaloyloxy-3,4-dihydronaphthalen-1(2H)-one 在 platinum(IV) oxide 盐酸 、 lithium aluminium tetrahydride 、 氢气 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 8.0h， 生成 (S)-1,2,3,4-tetrahydro-7-methoxy-1-methyl-1-naphthalenemethanol
  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 palladium on activated charcoal 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 锂硼氢 、 Celite 、 pH 8.04 phosphate buffer 、 硫酸 、 氢气 、 sodium hydride 、 N,N-二异丙基乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 丙酮 、 paraffin 、 苯 为溶剂， 反应 154.67h， 生成 (S)-(-)-6-methoxy-4-methyl-4-pivaloyloxy-3,4-dihydronaphthalen-1(2H)-one
  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.