(S)-(-)-1-formyl-1-methyl-7-methoxy-1,2,3,4-tetrahydronaphthalene | 161693-42-1

• 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)-(-)-1-formyl-1-methyl-7-methoxy-1,2,3,4-tetrahydronaphthalene
• 英文别名: (S)-1-Formyl-1-methyl-7-methoxy-1,2,3,4-tetrahydronaphthalene；(1S)-7-methoxy-1-methyl-3,4-dihydro-2H-naphthalene-1-carbaldehyde
• CAS: 161693-42-1
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: WOIJXABENMDEBU-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(-)-1-formyl-1-methyl-7-methoxy-1,2,3,4-tetrahydronaphthalene 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 paraffin 为溶剂， 反应 32.0h， 生成 methyl 3-(7-methoxy-1-methyl-1,2,3,4-tetrahydro-1-naphthyl)propionate
  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 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 、 乙醚 、 二氯甲烷 、 水 、 丙酮 、 paraffin 、 苯 为溶剂， 反应 164.67h， 生成 (S)-(-)-1-formyl-1-methyl-7-methoxy-1,2,3,4-tetrahydronaphthalene
  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 the Key Intermediates Leading to (-)-Aphanorphine and (-)-Eptazocine
  作者：Alison N. Hulme、Steven S. Henry、A. I. Meyers

  DOI：10.1021/jo00110a033

  日期：1995.3

  The asymmetric syntheses of two key intermediates, 8 and 15, in >99% ee are reported. These compounds are prepared by diastereofacial addition of lithiodimethylphenylsilane to chiral naphthyloxazolines followed by methyl iodide trapping. The two stereocenters are formed in greater than 95% ds, and the silyl center is subsequently removed to give the 1,1-disubstituted tetralins 8, 9, or 12. These chiral substances are readily transformed into the titled compounds as described in the literature. The absolute configuration of these intermediates has been confirmed by X-ray analysis and corrects an earlier misassignment.
• 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.