(1S,2S)-1-Hydroxy-6-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester | 156152-66-8

• 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-6-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester
• 英文别名: ethyl (1S,2S)-1-hydroxy-6-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate
• CAS: 156152-66-8
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: FMSCFVHWVDUZSD-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (1S,2S)-1-Hydroxy-6-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester 在 palladium on activated charcoal 、 高氯酸 、 hydroxide 、 氢气 作用下， 生成 (2S)-6-甲氧基-1,2,3,4-四氢-2-萘甲酸
  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：

  ethyl 6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate 在 Mucor racemosus 作用下， 反应 72.0h， 以40%的产率得到(1S,2S)-1-Hydroxy-6-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

• Practical and Efficient Enantioselective Borohydride Reduction of Aromatic Ketones Catalyzed by Optically Active Cobalt(II) Complexes Using Pre-Modified Borohydride
  作者：Kiyoaki D. Sugi、Takushi Nagata、Tohru Yamada、Teruaki Mukaiyama

  DOI：10.1246/cl.1996.1081

  日期：1996.12

  A catalytic enantioselective borohydride reduction of aromatic ketones in presence of 0.1-1 mol% of optically active aldiminato cobalt(II) complex catalysts at 0 °C was successfully achieved using precisely pre-modified borohydride with one equivalent each of tetrahydrofurfuryl alcohol, ethanol and NaBH4. The corresponding secondary alcohols were produced in less than 45 min with high enantiomeric

  使用精确预改性的硼氢化物与四氢糠醇、乙醇和 NaBH4 各一当量，在 0°C 下，在 0.1-1 mol% 的旋光醛亚氨基钴 (II) 配合物催化剂存在下，催化对映选择性硼氢化物还原芳族酮. 相应的仲醇在不到 45 分钟内以高对映体过量（高达 98% ee）生成。上述方法已成功应用于芳香酮的动力学和动态动力学拆分。
• METHODS AND PRECURSORS FOR THE PRODUCTION OF CHIRAL VICINAL AMINOALCOHOLS
  申请人：Biocatalytics, Inc.

  公开号：EP0991772A1

  公开（公告）日：2000-04-12
• US5942644A
  申请人：——

  公开号：US5942644A

  公开（公告）日：1999-08-24
• [EN] METHODS AND PRECURSORS FOR THE PRODUCTION OF CHIRAL VICINAL AMINOALCOHOLS<br/>[FR] PROCEDES ET PRECURSEURS UTILES POUR LA PRODUCTION D'AMINOALCOOLS VICINAUX CHIRAUX
  申请人：BIOCATALYTICS, INC.

  公开号：WO1998054350A1

  公开（公告）日：1998-12-03

  (EN) The disclosure describes a method for the preparation of chiral vicinal aminoalcohols in high optical purity. The method combines the stereoselective reduction of the keto group of a $g(b)-ketoacid, $g(b)-ketoester, or derivative with the stereospecific rearrangement of the corresponding amide, hyroxamic acid, or hydrazide to produce chiral vicinal aminoalcohols with control of stereochemistry at both chiral centers. The method involves novel precursor compounds.(FR) L'invention concerne un procédé utile pour la préparation d'aminoalcools vicinaux chiraux de grande pureté optique. Le procédé combine une réduction stéréosélective du groupe céto d'un $g(b)-cétoacide, d'un $g(b)-cétoester ou d'un dérivé avec le réaménagement stéréospécifique de l'amide, de l'acide hydroxamique ou de l'hydrazide correspondant, en vue de produire des aminoalcools vicinaux chiraux avec commande de la stéréochimie aux deux centres chiraux. Le procédé requiert l'utilisation de nouveaux composés de précurseurs.
• Microbial reduction of 1-tetralone 2-carboxyesters as a source of new asymmetric synthons
  作者：Didier Buisson、Roberto Cecchi、Jean-Alex Laffitte、Umberto Guzzi、Robert Azerad

  DOI：10.1016/s0040-4039(00)76837-7

  日期：1994.5

  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.