(R)-(+)-1,2-dihydro-1-(hydroxymethyl)-7-methoxy-1-methylnaphthalene | 128432-50-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-(+)-1,2-dihydro-1-(hydroxymethyl)-7-methoxy-1-methylnaphthalene
• 英文别名: (R)-(+)-1-hydroxymethyl-7-methoxy-1-methyl-1,2-dihydronaphthalene；(R)-1-hydroxymethyl-1-methyl-7-methoxy-1,2-dihydronaphthalene；[(1R)-7-methoxy-1-methyl-2H-naphthalen-1-yl]methanol
• CAS: 128432-50-8
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: RYCKOUCJKPFHIN-ZDUSSCGKSA-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：
  0.38
• 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-dihydro-1-(hydroxymethyl)-7-methoxy-1-methylnaphthalene 在 lead(IV) acetate 、 偶氮二甲酸二异丙酯 、 potassium carbonate 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 13.33h， 生成
  参考文献：
  名称：

  天然（–）-Aphanorphine的对映选择性全合成

  摘要：

  （-）-Aphanorphine是从淡水蓝绿色藻Aphanizomenon flos - aquae中分离出来的一种新型3-苯并ze庚因生物碱，已经以对映选择性的方式合成。

  DOI：

  10.1039/c39900000290
• 作为产物：
  描述：

  [1-(hydroxymethyl)-7-methoxy-2H-naphthalen-1-yl]methanol 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 173.0h， 生成 (R)-(+)-1,2-dihydro-1-(hydroxymethyl)-7-methoxy-1-methylnaphthalene
  参考文献：
  名称：

  Asymmetric construction of benzylic quaternary carbons by lipase-mediated enantioselective transesterification of prochiral α,α-disubstituted 1,3-propanediols

  摘要：

  The asymmetric differentiation by lipase-catalysed transesterification of prochiral alpha,alpha-disubstituted 1,3-propanediols 5 and 11 was accomplished in good enantiomeric excess and high chemical yield. The absolute configuration of the corresponding monoacetates (+)-2a and (-)-12a were determined by conversion into known key intermediates used in the synthesis of (-)-aphanorphine and (+)-eptazocine. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00500-9

文献信息

• Enantiodivergent Synthesis of the Key Intermediate for Aphanorphine by Chemoenzymatic Process
  作者：Keith O. Hallinan、Toshio Honda

  DOI：10.1016/0040-4020(95)00784-6

  日期：1995.11

  A short chemoenzymatic route to both enantiomers of the key intermediate (12) in the preparation of aphanorphine is described. Enzymatic hydrolysis of the prochiral malonate (8) followed by selective reduction was achieved in very high ee (>99%).

  描述了在制备甲啡肽中至关键中间体（12）的两个对映异构体的短化学酶促路线。在非常高的ee（> 99％）中实现了前手性丙二酸酯的酶促水解（8），然后选择性还原。
• Asymmetric construction of benzylic quaternary carbons from chiral malonates: Formal synthesis of natural (−)aphanorphine
  作者：Antoine Fadel、Philippe Arzel

  DOI：10.1016/0957-4166(95)00097-9

  日期：1995.4

  Enantiomerically pure (+)-dihydronaphthalene 4, a precursor of (-)-aphanorphine, was obtained from the homochiral malonic acid ester (R)-(+)-5, via the chiral lactone (+)-12 prepared by a Wittig-Horner reaction and hydrogenation, which underwent subsequent acidic Friedel-Crafts cyclisation.
• 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.