(S)-(+)-3-(tert-butyldimethylsiloxy)-2-(3-methoxyphenyl)-2-methyl-1-propanol | 163981-36-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-(+)-3-(tert-butyldimethylsiloxy)-2-(3-methoxyphenyl)-2-methyl-1-propanol
• 英文别名: (S)-(+)-3-(tert-butyldimethylsilyloxy)-2-(3-methoxyphenyl)-2-methylpropanol；(2S)-3-[tert-butyl(dimethyl)silyl]oxy-2-(3-methoxyphenyl)-2-methylpropan-1-ol
• CAS: 163981-36-0
• 化学式: C₁₇H₃₀O₃Si
• 分子量: 310.509
• InChiKey: HAUDOQAGEDWTDK-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(+)-3-(tert-butyldimethylsiloxy)-2-(3-methoxyphenyl)-2-methyl-1-propanol 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-(-)-3-(tert-butyldimethylsilyloxy)-2-(3-methoxyphenyl)-2-methylpropanal
  参考文献：
  名称：

  Asymmetric construction of benzylic quaternary carbons from chiral malonates: Formal synthesis of natural (−)aphanorphine

  摘要：

  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.

  DOI：

  10.1016/0957-4166(95)00097-9
• 作为产物：
  描述：

  2-(3-methoxyphenyl)-2-methylpropane-1,3-diol 在 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 108.0h， 生成 (S)-(+)-3-(tert-butyldimethylsiloxy)-2-(3-methoxyphenyl)-2-methyl-1-propanol
  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 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.
• 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.