(R)-1,2,3,4-tetrahydro-7-methoxy-1-methyl-1-naphthalenemethanol | 178681-61-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (R)-1,2,3,4-tetrahydro-7-methoxy-1-methyl-1-naphthalenemethanol
• 英文别名: [(1R)-7-methoxy-1-methyl-3,4-dihydro-2H-naphthalen-1-yl]methanol
• CAS: 178681-61-3
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: ASNWBNLDNNHQFP-ZDUSSCGKSA-N

物化性质

• 沸点：
  326.2±35.0 °C(Predicted)
• 密度：
  1.045±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1,2,3,4-tetrahydro-7-methoxy-1-methyl-1-naphthalenemethanol 在 platinum(IV) oxide 、 palladium on activated charcoal potassium dichromate 、 sodium hydroxide 、 sodium tetrahydroborate 、 高氯酸 、 Celite 、 硫酸 、 盐酸羟胺 、 氢气 、 溴 、 sodium methylate 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 、 苯 为溶剂， 反应 179.0h， 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 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 锂硼氢 、 Celite 、 pH 8.04 phosphate buffer 、 硫酸 、 氢气 、 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 、 丙酮 、 paraffin 、 苯 为溶剂， 反应 123.83h， 生成 (R)-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

文献信息

• An efficient asymmetric synthesis of key intermediates in the synthesis of aphanorphine and eptazocine
  作者：Stephen K. Taylor、Milica Ivanovic、Lloyd J. Simons、Matthew M. Davis

  DOI：10.1016/s0957-4166(03)00117-4

  日期：2003.3

  Efficient, formal syntheses of aphanorphine and eptazocine are reported that involve epoxide cyclizations. The necessary chiral epoxides were prepared following treatment of diols prepared by Sharpless asymmetric osmylations of an alkene. The cyclizations formed a ring compound with the same enantiomeric purity as the starting epoxide.

  据报道，涉及环氧化物环化的高效，正式的甲啡肽和庚唑碱合成。在处理通过烯烃的Sharpless不对称渗透作用制备的二醇之后，制备必要的手性环氧化物。环化形成具有与起始环氧化物相同的对映体纯度的环化合物。
• Enzymatic asymmetrisation of prochiral α,α-disubstituted-malonates and -1,3-propanediols: formal asymmetric syntheses of (−)-aphanorphine and (+)-eptazocine
  作者：Antoine Fadel、Philippe Arzel

  DOI：10.1016/s0957-4166(96)00538-1

  日期：1997.2

  Formal asymmetric syntheses of (-)-aphanorphine and (+)-eptazocine are reported via the two key intermediates 3a and 3b obtained in 94-97% ee, from the readily available chirons (R)-5 and (R)-9. Which resulting from enzyme-catalysed asymmetrisation of prochiral alpha,alpha-disubstituted-1,3-propanediols and -malonates respectively. (C) 1997 Elsevier Science Ltd. All rights reserved.
• 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.