(2S,3S)-3-Hydroxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid methyl ester | 184587-38-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S,3S)-3-Hydroxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,3S)-3-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate
• CAS: 184587-38-0
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: JAXSMYYWJCYMPM-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S)-(-)-莰烷酰氯 、 (2S,3S)-3-Hydroxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid methyl ester 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以77%的产率得到
  参考文献：
  名称：

  Selective synthesis of 1-, and 3-carbomethoxy 2-tetralol stereoisomers by microbial reduction of the corresponding tetralones

  摘要：

  The microbial reduction of beta-ketoesters derived from 2-tetralone has been shown to produce good yields of 2-hydroxy-1-carboxy- or 3-hydroxy-2-carboxyesters. Baker's yeast invariably affords a high enantiomeric purity cis-hydroxyester, while fungi strains may produce, sometimes exclusively, cis- or trans- complementary stereochemistries. From a general survey of the baker's yeast reduction of cyclic beta-ketoesters, a working model for predicting enantio- and diastereoselectivities of the reduction is proposed and discussed. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00389-8
• 作为产物：
  描述：

  3-carbomethoxy-2-tetralone 以 乙醇 为溶剂， 反应 24.0h， 以76%的产率得到(2S,3S)-3-Hydroxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Selective synthesis of 1-, and 3-carbomethoxy 2-tetralol stereoisomers by microbial reduction of the corresponding tetralones

  摘要：

  The microbial reduction of beta-ketoesters derived from 2-tetralone has been shown to produce good yields of 2-hydroxy-1-carboxy- or 3-hydroxy-2-carboxyesters. Baker's yeast invariably affords a high enantiomeric purity cis-hydroxyester, while fungi strains may produce, sometimes exclusively, cis- or trans- complementary stereochemistries. From a general survey of the baker's yeast reduction of cyclic beta-ketoesters, a working model for predicting enantio- and diastereoselectivities of the reduction is proposed and discussed. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00389-8

文献信息

• Selective synthesis of 1-, and 3-carbomethoxy 2-tetralol stereoisomers by microbial reduction of the corresponding tetralones
  作者：Cécile Abalain、Didier Buisson、Robert Azerad

  DOI：10.1016/0957-4166(96)00389-8

  日期：1996.10

  The microbial reduction of beta-ketoesters derived from 2-tetralone has been shown to produce good yields of 2-hydroxy-1-carboxy- or 3-hydroxy-2-carboxyesters. Baker's yeast invariably affords a high enantiomeric purity cis-hydroxyester, while fungi strains may produce, sometimes exclusively, cis- or trans- complementary stereochemistries. From a general survey of the baker's yeast reduction of cyclic beta-ketoesters, a working model for predicting enantio- and diastereoselectivities of the reduction is proposed and discussed. Copyright (C) 1996 Elsevier Science Ltd