(R)-1-(3-chlorophenyl)-2,2,2-trifluoroethanol | 376347-10-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-1-(3-chlorophenyl)-2,2,2-trifluoroethanol
• 英文别名: (R)-2,2,2-Trifluoro-1-(3-chlorophenyl)ethanol；(1R)-1-(3-chlorophenyl)-2,2,2-trifluoroethanol
• CAS: 376347-10-3
• 化学式: C₈H₆ClF₃O
• 分子量: 210.583
• InChiKey: IFUMGCOCVZUIRR-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氯-2,2,2-三氟苯乙酮 在 Almag CRED A₁₃₁ 、 NADP 、 glucose dehydrogenase 作用下， 以 水 、 二甲基亚砜 、 异丙醇 为溶剂， 以89%的产率得到(R)-1-(3-chlorophenyl)-2,2,2-trifluoroethanol
  参考文献：
  名称：

  Preparative access to medicinal chemistry related chiral alcohols using carbonyl reductase technology

  摘要：

  Libraries of highly enantioenriched secondary alcohols in both enantiomeric forms were synthesised by enzymatic reduction of their parent ketones using selectAZyme (TM) carbonyl reductase (CRED) technology. Commercially available CREDs were able to reduce a range of substrate classes efficiently and with very high enantioselectivity. Matching substrate classes to small subsets of CREDs enabled the fast development of preparative bioreductions and the rapid generation of 100-1500 mg samples of chiral alcohols in typically >95% ee and the majority in >= 99.0% ee. The conditions for small scale synthesis were then scaled up to 0.5 kg to deliver one of the chiral alcohols, (S)-1-(4-bromophenyl)-2-chloroethanol, in 99.8% ee and 91% isolated yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.015

文献信息

• Asymmetric Hydrogenation of Aryl Perfluoroalkyl Ketones Catalyzed by Rhodium(III) Monohydride Complexes Bearing Josiphos Ligands
  作者：Fabian Brüning、Haruki Nagae、Daniel Käch、Kazushi Mashima、Antonio Togni

  DOI：10.1002/chem.201902585

  日期：2019.8.14

  The asymmetric hydrogenation of 2,2,2-trifluoroacetophenones and aryl perfluoroalkyl ketones was developed using a unique, well-defined chloride-bridged dinuclear rhodium(III) complex bearing Josiphos-type diphosphine ligands. These complexes were prepared from [RhCl(cod)]2 , Josiphos ligands, and hydrochloric acid. As catalyst precursors, they allow for the efficient and enantioselective synthesis

  2，2，2-三氟苯乙酮和芳基全氟烷基酮的不对称氢化反应是使用独特的，定义明确的带有Josiphos型二膦配体的氯桥联二核铑（III）络合物开发的。这些配合物是由[RhCl（cod）] 2，Josiphos配体和盐酸制备的。作为催化剂的前体，它们允许具有全氟烷基的手性仲醇的有效和对映选择性合成（最高99％ee）。该系统不需要用于2,2,2-三氟苯乙酮氢化的活化碱。另外，首次报道了2-苯基-3-（卤代乙酰基）吲哚的对映选择性C ＝ O氢化，这是药物化学中的一类特权结构。
• Caspase inhibtors and uses thereof
  申请人：——

  公开号：US20020061853A1

  公开（公告）日：2002-05-23

  This invention provides caspase inhibitors having the formula 1 wherein Ring A is an optionally substituted piperidine, tetrahydroquinoline or tetrahydroisoquinoline ring; R 1 is hydrogen, CHN 2 , R, or —CH 2 Y; R is an optionally substituted group selected from an aliphatic group, an aryl group, an aralkyl group, a heterocyclic group, or an heterocyclylalkyl group; Y is an electronegative leaving group; R 2 is CO 2 H, CH 2 CO 2 H, or esters, amides or isosteres thereof; Ar is an optionally substituted aryl group; and R 3 is hydrogen, an optionally substituted C 1-6 alkyl, F 2 , CN, aryl or R 3 is attached to Ar to form an unsaturated or partially saturated five or six membered fused ring having 0-2 heteroatoms. The compounds are useful for treating caspase-mediated diseases in mammals.

  这项发明提供了具有以下结构的caspase抑制剂： 其中Ring A是可选择取代的哌啶、四氢喹啉或四氢异喹啉环；R1是氢、CHN2、R或—CH2Y；R是从脂肪基、芳基、芳基烷基、杂环基或杂环烷基中选择的可选择取代基；Y是电负离子离去基团；R2是CO2H、CH2CO2H或它们的酯、酰胺或同分异构体；Ar是可选择取代的芳基；R3是氢、可选择取代的C1-6烷基、F2、CN、芳基或R3连接到Ar以形成具有0-2个杂原子的不饱和或部分饱和的五元或六元融合环。这些化合物可用于治疗哺乳动物中的caspase介导的疾病。
• The enantioselective trifluoromethylation of aromatic aldehydes by quaternary ammonium bromide and (IPr)CuF at low catalyst loading
  作者：Shaoxiang Wu、Jiyi Guo、Muhammad Sohail、Chengyao Cao、Fu-Xue Chen

  DOI：10.1016/j.jfluchem.2013.01.027

  日期：2013.4

  A general catalytic enantioselective trifluoromethylation of aromatic aldehydes using (IPr)CuF and quinidine-derived quaternary ammonium salt as catalysts has been developed. A wide range of aromatic aldehydes are converted to the corresponding products in up to 92% yield and 81% ee at 2 mol% of catalyst loading. (C) 2013 Elsevier B.V. All rights reserved.
• Cinchona alkaloid/TMAF combination: Enantioselective trifluoromethylation of aryl aldehydes
  作者：Hiroyuki Kawai、Satoshi Mizuta、Etsuko Tokunaga、Norio Shibata

  DOI：10.1016/j.jfluchem.2013.01.032

  日期：2013.8

  The catalytic enantioselective trifluoromethylation reaction of aromatic aldehydes using the Ruppert-Prakash reagent (Me3SiCF3) has been disclosed, with an operationally simple procedure, based on the combination of sterically demanding cinchona alkaloid-derived phase-transfer catalyst 3b with tetramethylammonium fluoride (TMAF). Our methodology provides medicinally important alpha-trifluoromethyl alcohols with high chemical yields and moderate to good enantioselectivities (50-70% ee). (c) 2013 Elsevier B.V. All rights reserved.
• CASPASE INHIBITORS AND USES THEREOF
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：EP1283827A2

  公开（公告）日：2003-02-19