(1S,2S)-1-Hydroxy-5-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester | 156152-64-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S,2S)-1-Hydroxy-5-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester
• 英文别名: ethyl (1S,2S)-1-hydroxy-5-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate
• CAS: 156152-64-6
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: BJLPJUQPXVNWMK-WCQYABFASA-N

物化性质

• 沸点：
  391.4±42.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,2S)-1-Hydroxy-5-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester 在 palladium on activated charcoal 、 sodium azide 、 高氯酸 、 草酰氯 、 hydroxide 、 氢气 、 氢气 作用下， 生成 (S)-2-氨基-5-甲氧基四氢萘盐酸盐
  参考文献：
  名称：

  Microbial reduction of 1-tetralone 2-carboxyesters as a source of new asymmetric synthons

  摘要：

  The reduction of unsubstituted or methoxy-substituted (+/-)-2-carboxyethyl-1-tetralones by selected microorganisms affords optically active 1-hydroxy-2-carboxyethyl tetralins which can be used as versatile asymmetric synthons, for example in the preparation of biologically active methoxy-substituted 2R-aminotetralins. 1R,2R-(cis)-hydroxyesters of high optical purity are obtained with yeast strains, while the use of filamentous fungi leads to the enantiomeric 1S,2S-(cis)-hydroxyesters.

  DOI：

  10.1016/s0040-4039(00)76837-7
• 作为产物：
  描述：

  5-methoxy-2-(ethoxycarbonyl)tetralone 在 Sporotrichum exile QM 1250 作用下， 反应 48.0h， 以51%的产率得到(1S,2S)-1-Hydroxy-5-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Microbial reduction of 1-tetralone 2-carboxyesters as a source of new asymmetric synthons

  摘要：

  The reduction of unsubstituted or methoxy-substituted (+/-)-2-carboxyethyl-1-tetralones by selected microorganisms affords optically active 1-hydroxy-2-carboxyethyl tetralins which can be used as versatile asymmetric synthons, for example in the preparation of biologically active methoxy-substituted 2R-aminotetralins. 1R,2R-(cis)-hydroxyesters of high optical purity are obtained with yeast strains, while the use of filamentous fungi leads to the enantiomeric 1S,2S-(cis)-hydroxyesters.

  DOI：

  10.1016/s0040-4039(00)76837-7

文献信息

• Dynamic kinetic resolution of cyclic β-ketoesters with preformed or prepared in situ chiral diphosphine-ruthenium (II) catalysts
  作者：J.P Genêt、X Pfister、V Ratovelomanana-Vidal、C Pinel、J.A Laffitte

  DOI：10.1016/s0040-4039(00)60727-x

  日期：1994.6

  The reduction of racemic beta-keto esters having the tetralone structure by chiral ruthenium(II) catalysts is realized with an ideal kinetic dynamic resolution. Remarkably, high anti selectivity approaching 100% and enantioselectivity (up to 97%) using atropisomeric ligands are obtained. The trans beta-hydroxy esters thus available are useful starting materials for production of enantiomerically pure compounds.