(alphaR)-alpha-(2-氯乙基)-4-氟苯甲醇 | 200004-39-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (alphaR)-alpha-(2-氯乙基)-4-氟苯甲醇
• 中文别名: (R)-3-氯-1-(4-氟苯基)-1-丙醇
• 英文名称: (R)-3-chloro-1-(4-fluorophenyl)propan-1-ol
• 英文别名: (R)-3-chloro-1-(4-fluorophenyl)-1-propanol；(1R)-3-chloro-1-(4-fluorophenyl)propan-1-ol
• CAS: 200004-39-3
• 化学式: C₉H₁₀ClFO
• 分子量: 188.629
• InChiKey: GQGPYILQJAINSJ-SECBINFHSA-N

物化性质

• 沸点：
  297.8±25.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (alphaR)-alpha-(2-氯乙基)-4-氟苯甲醇 在 氢氧化钾 、 sodium iodide 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Ezetimibe analogs with a reorganized azetidinone ring: Design, synthesis, and evaluation of cholesterol absorption inhibitions

  摘要：

  The underlying principle of drug design in this paper is that the maximum retention of the functional groups that exist in the marketed drug would provide a higher probability for comparable safety while the conformational changes in the newly created analogs should not constitute a significant structural variation to adversely affect biological activity. Four individual isomers of backbone re-organized ezetimibe analogs were designed and synthesized. Their effects on the cholesterol levels in rat serum were evaluated by a high-cholesterol and high-fat diet feeding experiment. All the new analogs showed significant effect in lowering the levels of total cholesterol in serum. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.078
• 作为产物：
  描述：

  (-)-3-chloro-1-(4-fluorophenyl)propan-1-ol 在 lipase from Pseudomonas fluorescens 、 lipase from Candida rugosa 作用下， 以 正己烷 为溶剂， 反应 71.5h， 生成 (alphaR)-alpha-(2-氯乙基)-4-氟苯甲醇
  参考文献：
  名称：

  脂肪酶催化的3-氯-1-芳基丙烷-1-醇的两种对映体的合成

  摘要：

  脂肪酶催化3-氯-1-（4-氟苯基）丙-1-醇，3-氯-1-（4-碘苯基）丙-1-醇和3-氯-1-醇的两种对映体的合成描述了苯基丙-1-醇。该方法是基于在荧光假单胞菌（LAK）的脂肪酶存在下外消旋醇的对映异构体选择性酰化，然后是来自假丝酵母（CRL）的脂肪酶介导的先前获得的对映异构体富集的1-芳基-3-氯丙基酯的水解。对于生产对映纯（S）-1-芳基-3-氯丙烷-1-醇（99％ee，收率34-42％），以高于理论最佳50％的转化率停止反应，而对映纯（[R）-1-芳基-3-氯丙基乙酸酯（99％ee）以较低的转化率停止反应。将后面的化合物酶水解为相应的（R）-1-芳基-3-氯丙烷-1-醇（97-99％ee，18-24％收率）。分辨率产品的绝对配置是通过VCD测量结合量子化学计算来确定的。 酶-动力学拆分-对映选择性-手性拆分-醇类-卤化物

  DOI：

  10.1055/s-0030-1260149

文献信息

• Ultrafast Iron-Catalyzed Reduction of Functionalized Ketones: Highly Enantioselective Synthesis of Halohydrines, Oxaheterocycles, and Aminoalcohols
  作者：Clemens K. Blasius、Vladislav Vasilenko、Lutz H. Gade

  DOI：10.1002/anie.201806196

  日期：2018.8.6

  A molecularly defined chiral boxmi iron alkyl complex catalyzes the hydroboration of various functionalized ketones and provides the corresponding chiral halohydrines, oxaheterocycles (oxiranes, oxetanes, tetrahydrofurans, and dioxanes) and amino alcohols with excellent enantioselectivities (up to >99 %ee) and conversion efficiencies at low catalyst loadings (as low as 0.5 mol %). Turnover frequencies

  分子定义的手性boxmi铁烷基络合物催化各种官能化酮的氢硼化，并提供相应的手性卤代醇，氧杂杂环（环氧乙烷，氧杂环丁烷，四氢呋喃和二恶烷）和氨基醇，具有出色的对映选择性（高达> 99％ee）和转化效率在低催化剂负载量（低至0.5 mol％）下。在−30°C时，周转频率大于40000 h -1突显了这种富含地球的金属催化剂的活性，该催化剂可耐受许多官能团。
• 중간체로서 광학 활성 3-아미노-1-페닐프로판올 유도체의 제조방법 및 상기 중간체를 이용한 광학 활성 약학적 산물의 제조방법
  申请人：KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY 한국화학연구원(319980077651)

  公开号：KR20150116956A

  公开（公告）日：2015-10-19

  본 발명은 스피로보레이트 에스테르(spiroborate ester) 촉매 및 수소공여체의 존재 하에 비대칭 환원반응시키는 단계를 포함하는, 80% 이상의 거울상 이성질체 잉여율(enanthiomeric excess; ee)로 (R) 또는 (S)의 광학 활성을 갖는 3-아미노-1-페닐프로판올 유도체를 제조하는 방법; 및 상기 촉매를 이용하여 중간체인 (R)- 또는 (S)-3-아미노-1-페닐프로판올 유도체를 생산하는 단계를 포함하는, 광학 활성 약학적 산물을 제조하는 방법에 관한 것이다.

  这项发明涉及一种制备具有80%以上对映体过量率（enanthiomeric excess; ee）为(R)或(S)的光学活性的3-氨基-1-苯丙醇衍生物的方法，其中包括在存在螺环硼酸酯(spiroborate ester)催化剂和氢供体的情况下进行不对称还原反应的步骤；以及涉及一种利用该催化剂生产(R)-或(S)-3-氨基-1-苯丙醇衍生物中间体的步骤，从而制备光学活性药物产物的方法。
• Asymmetric synthesis of 2-aryl substituted oxetanes by enantioselective reduction of β-halogenoketones using lithium borohydride modified with N,N′-dibenzoylcystine
  作者：Kenso Soai、Seiji Niwa、Takashi Yamanoi、Hitoshi Hikima、Miyuki Ishizaki

  DOI：10.1039/c39860001018

  日期：——

  Optically active 2-aryl substituted oxetanes are synthesised in high enantiomeric excesses (up to 89% e.e.)via enantioselective reduction of β-halogenoketones with lithium borohydride using (R,R′)-N,N′-dibenzoylcystine and t-butyl alcohol as ligands.

  通过使用（R，R '）- N，N'-二苯甲酰基胱氨酸和叔丁醇作为对映体，通过硼氢化锂与β-卤代酮的对映选择性还原，以高对映体过量（最多89％ee）合成旋光的2-芳基氧杂环丁烷配体。
• Pharmaceutical for treatment of neurological and neuropsychiatric disorders
  申请人：——

  公开号：US20010012857A1

  公开（公告）日：2001-08-09

  The invention provides a pharmaceutical for treatment of neurological and neuropsychiatric disorders comprising a compound of the formula: 1 or a pharmaceutically acceptable salt thereof.

  该发明提供了一种用于治疗神经和神经精神障碍的药物，包括式1的化合物或其药学上可接受的盐。
• Highly enantioselective reduction of achiral ketones with NaBH4/Me3SiCl catalyzed by (S)-α,α-diphenylpyrrolidinemethanol
  作者：Biao Jiang、Yan Feng、Jian Zheng

  DOI：10.1016/s0040-4039(00)01848-7

  日期：2000.12

  The reducing agent prepared from sodium borohydride, trimethylsilyl chloride and a catalytic amount of (S)-alpha,alpha -diphenylpyrrolidinemethanol has been successfully applied to the enantioselective reduction of ketones. The optically active secondary alcohols were obtained in excellent enantiomeric excess and almost quantitative chemical yield. (C) 2000 Elsevier Science Ltd. All rights reserved.