(S)-2-chloro-1-(pyridin-3-yl)ethanol | 515179-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (S)-2-chloro-1-(pyridin-3-yl)ethanol
• 英文别名: (S)-2-chloro-1-(3-pyridyl)-ethanol；(S)-3-(1-hydroxy-2-chloroethyl)-pyridine；(S)-α-chloromethyl-3-pyridine-methanol；(S)-chloromethyl-3-pyridinemethanol；(1S)-2-chloro-1-pyridin-3-ylethanol
• CAS: 515179-33-6
• 化学式: C₇H₈ClNO
• 分子量: 157.6
• InChiKey: LCBCRIBFOZSPJL-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-chloro-1-(pyridin-3-yl)ethanol 在 氢氧化钾 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.25h， 生成 (S)-1-(3-pyridyl)-2-(methylamino)ethanol
  参考文献：
  名称：

  Solvent and in situ catalyst preparation impacts upon Noyori reductions of aryl-chloromethyl ketones: application to syntheses of chiral 2-amino-1-aryl-ethanols

  摘要：

  As part of medicinal chemistry efforts we found it necessary to develop general syntheses of highly enantiomerically enriched 1-aryl-2-chloroethanols and 1-aryl-2-methylaminoethanols. A survey of literature methods suggested that a truly general approach had not yet been reported, encouraging us to undertake the development of such a methodology. This study describes the design, development, and reduction to practice of a general synthesis of chiral 1-aryl-2-chloroethanols and the transformation of these entities to highly enantiomerically enriched 1-aryl-2-methylaminoethanols. Of particular importance were observations of the impact of solvent and the method of catalyst preparation on the yield and enantiomerical excess of chlorohydrins prepared via Noyori transfer hydrogenations of aryl-chloromethyl ketones. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.017
• 作为产物：
  描述：

  3-(2-氯乙酰基)吡啶盐酸盐 在 NADP+ 、 L-(-)-glucose 作用下， 以 水 为溶剂， 反应 25.0h， 以99.8%的产率得到
  参考文献：
  名称：

  PROCESS FOR PREPARATION OF (S)-ALPHA-HALOME THYLPYRIDINE METHANOL DERIVATIVES

  摘要：

  本发明提供了一种从廉价原料中轻松制备(S)-α-卤甲基吡啶-甲醇衍生物的方法，该衍生物可用作制药产品的中间体。该(S)-α-卤甲基吡啶-甲醇衍生物是通过使用具有(S)-选择性还原2-卤乙酰吡啶衍生物的羧酸还原酶源制备的，该酶源能够(S)-选择性地还原2-卤乙酰吡啶衍生物，而该酶源可以廉价获得。此外，使用氢卤酸和有机溶剂从含杂质的(S)-α-卤甲基-3-吡啶甲醇衍生物中分离纯化出(S)-α-卤甲基-3-吡啶甲醇衍生物的氢卤酸盐晶体。

  公开号：

  EP1454899A1

文献信息

• [EN] PROCESS TO PRODUCE ENANTIOMERICALLY ENRICHED 1-ARYL- AND 1-HETEROARYL-2-AMINOETHANOLS<br/>[FR] PROCEDE DE PREPARATION D'1-ARYL- ET D'1-HETEROARYL-2-AMINOETHANOLS ENRICHIS EN ENANTIOMERES
  申请人：UPJOHN CO

  公开号：WO2004085414A1

  公开（公告）日：2004-10-07

  The invention relates to a method of preparing enantiomerically enriched amino alcohols of Formula (I) wherein the variable R1, R2, and R3 are defined herein.

  这项发明涉及一种制备式(I)的对映体富集氨基醇的方法，其中变量R1、R2和R3在此处被定义。
• A practical synthesis of optically active aromatic epoxides via asymmetric transfer hydrogenation of α-chlorinated ketones with chiral rhodium–diamine catalyst
  作者：Takayuki Hamada、Takayoshi Torii、Kunisuke Izawa、Takao Ikariya

  DOI：10.1016/j.tet.2004.06.076

  日期：2004.8

  A practical method for the synthesis of optically active aromatic epoxides has been developed via the formation of optically active α-chlorinated alcohols and intramolecular etherification. Optically active alcohols with up to 99% ee can be obtained from the asymmetric reduction of aromatic ketones with a substrate/catalyst ratio of 1000–5000 using a formic acid/triethylamine mixture containing a well-defined

  通过形成光学活性的α-氯化醇和分子内醚化，已经开发了一种合成光学活性的芳族环氧化物的实用方法。使用含有明确定义的手性Rh络合物Cp * RhCl [（[R， [R）-Tsdpen]。由于二胺基Cp * Rh（III）氢化物配合物的配位饱和特性，用手性Rh催化剂不对称还原α-氯化芳族酮的特征是快速且羰基选择性转化。还原的结果受酮底物的结构以及氢源（如甲酸或2-丙醇）的影响很大。无需特殊纯化即可在该反应中使用市售的试剂和溶剂。一锅法或两锅法的这种环氧化物合成方法是实用的，对于从α-氯代酮大规模生产旋光性苯乙烯氧化物特别有用。
• Process for preparation of (s)-alpha-halomethylpyridine-methanol derivatives
  申请人：——

  公开号：US20040265991A1

  公开（公告）日：2004-12-30

  The present invention provides a process for easily preparing a (S)-&agr;-halomethylpyridine-methanol derivative, which is useful as an intermediate of pharmaceutical products, from inexpensive raw materials. The (S)-&agr;-halomethylpyridine-methanol derivative is prepared by (S)-selectively reducing a 2-haloacetylpyridine derivative using an enzyme source having ability to (S)-selectively reduce a carbonyl group of the 2-haloacetylpyridine derivative, which can be obtained inexpensively. Also, a hydrohalic acid salt of (S)-&agr;-halomethyl-3-pyridine-methanol derivative is isolated and purified as crystal from a (S)-&agr;-halomethyl-3-pyridine-methanol derivative containing impurities using hydrohalic acid and an organic solvent.

  本发明提供了一种从廉价原料中轻松制备(S)-α-卤甲基吡啶甲醇衍生物的方法，该衍生物可用作制药产品的中间体。通过使用具有(S)-选择性还原2-卤乙酰吡啶衍生物的能力的酶源(S)-选择性还原2-卤乙酰吡啶衍生物来制备(S)-α-卤甲基吡啶甲醇衍生物，该酶源可以廉价获得。此外，使用氢卤酸和有机溶剂从含杂质的(S)-α-卤甲基-3-吡啶甲醇衍生物中分离和纯化(S)-α-卤甲基-3-吡啶甲醇衍生物的氢卤酸盐作为晶体。
• NOVEL SULFONAMIDE SUBSTITUTED CHROMAN DERIVATIVES USEFUL AS BETA-3 ADRENORECEPTOR AGONISTS
  申请人：BAYER CORPORATION

  公开号：EP1054881B1

  公开（公告）日：2008-07-30
• A chemoenzymatic scalable route to optically active (R)-1-(pyridin-3-yl)-2-aminoethanol, valuable moiety of β3-adrenergic receptor agonists
  作者：Maria Grazia Perrone、Ernesto Santandrea、Erika Giorgio、Laura Bleve、Antonio Scilimati、Paolo Tortorella

  DOI：10.1016/j.bmc.2005.09.046

  日期：2006.2

  Enantiomerically pure (R)-2-chloro-1-(pyridin-3-yl)ethanol has been prepared by kinetic resolution performed in the presence of Candida antarctica SP435-L lipase immobilized on a macroporous polyacrylate resin (Novozym 4350). It was converted into (R)-1-(pyridin-3-yl)-2- aminoethanol, left-hand side of beta(3)-adrenergic receptor ligands. (c) 2005 Elsevier Ltd. All rights reserved.