(R)-(-)-1-acetoxymethyl-1-hydroxymethyl-7-methoxy-1,2-dihydronaphthalene | 187725-47-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-(-)-1-acetoxymethyl-1-hydroxymethyl-7-methoxy-1,2-dihydronaphthalene
• 英文别名: [(1R)-1-(hydroxymethyl)-7-methoxy-2H-naphthalen-1-yl]methyl acetate
• CAS: 187725-47-9
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: JRWHRFVRSQZJPX-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(-)-1-acetoxymethyl-1-hydroxymethyl-7-methoxy-1,2-dihydronaphthalene 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 5.0h， 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
• 作为产物：
  描述：

  dimethyl 7-methoxy-1,2-dihydronaphthalene-1,1-dicarboxylate 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 120.0h， 生成 (R)-(-)-1-acetoxymethyl-1-hydroxymethyl-7-methoxy-1,2-dihydronaphthalene
  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

• 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 construction of benzylic quaternary carbons by lipase-mediated enantioselective transesterification of prochiral α,α-disubstituted 1,3-propanediols
  作者：Antoine Fadel、Philippe Arzel

  DOI：10.1016/s0957-4166(96)00500-9

  日期：1997.1

  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.