(1S,2R)-3,3,3-trifluoro-1-phenylpropane-1,2-diol | 1158080-67-1

• 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: (1S,2R)-3,3,3-trifluoro-1-phenylpropane-1,2-diol
• CAS: 1158080-67-1
• 化学式: C₉H₉F₃O₂
• 分子量: 206.164
• InChiKey: MDBJXMJLAMRDMG-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  光气 、 (1S,2R)-3,3,3-trifluoro-1-phenylpropane-1,2-diol 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 4-phenyl-5-(trifluoromethyl)-1,3-dioxolan-2-one
  参考文献：
  名称：

  Ring-Opening of 1-CF3-Substituted Epoxy Ethers with Carboxylic, Thiocarboxylic, and Phosphinic Acids in Basic Medium and in Hexafluoro-2-propanol

  摘要：

  Ring-opening of 1-CF3-substituted epoxy ethers with carboxylic acids was achieved in Et3N as solvent, and alpha-CF3-substituted acyloins and corresponding esters were obtained in good yields. In hexafluoro-2-propanol (HFIP) as solvent, the carboxylic acids acted as nucleophiles, and alpha-carbonyloxy trifluoromethyl ketones were isolated in good yields. After reduction, CF3-substituted glycols were obtained as monoesters on one or the other hydroxy group. This reaction also allowed the preparation of alpha-carbonylsulfanyl- and alpha-phosphoryloxy trifluoromethyl ketones and corresponding alcohols. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200210)2002:20<3402::aid-ejoc3402>3.0.co;2-m
• 作为产物：
  描述：

  3,3,3-trifluoro-2-oxo-1-phenylpropyl benzoate 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 水 为溶剂， 反应 1.08h， 生成 (1S,2R)-3,3,3-trifluoro-1-phenylpropane-1,2-diol
  参考文献：
  名称：

  Ring-Opening of 1-CF3-Substituted Epoxy Ethers with Carboxylic, Thiocarboxylic, and Phosphinic Acids in Basic Medium and in Hexafluoro-2-propanol

  摘要：

  Ring-opening of 1-CF3-substituted epoxy ethers with carboxylic acids was achieved in Et3N as solvent, and alpha-CF3-substituted acyloins and corresponding esters were obtained in good yields. In hexafluoro-2-propanol (HFIP) as solvent, the carboxylic acids acted as nucleophiles, and alpha-carbonyloxy trifluoromethyl ketones were isolated in good yields. After reduction, CF3-substituted glycols were obtained as monoesters on one or the other hydroxy group. This reaction also allowed the preparation of alpha-carbonylsulfanyl- and alpha-phosphoryloxy trifluoromethyl ketones and corresponding alcohols. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200210)2002:20<3402::aid-ejoc3402>3.0.co;2-m

文献信息

• Convenient synthesis of optically active deuterated primary alcohols via deuteride reduction of acetals derived from homochiral (1R∗,2R∗)-3,3,3-trifluoro-1-phenylpropane-1,2-diols
  作者：Carlo F. Morelli、Paola Cairoli、Tiziana Marigolo、Giovanna Speranza、Paolo Manitto

  DOI：10.1016/j.tetasy.2009.01.020

  日期：2009.2

  (1R)-1-Deuterated alcohols with high enantiomeric excess were prepared via TiCl4/Et3SiD reduction of acetals arising from the reaction of aldehydes with (1S,2S)-3,3,3-trifluoro-1-phenylpropane-1,2-diol 9. Such a chiral auxiliary was synthesized in an enantiomerically pure form starting from L-mandelic acid. Due to its benzylic nature, it was easily removed from the reaction product of the reductive 1,3-dioxolane ring-cleavage to afford the desired alpha-deuterated alcohol. (C) 2009 Elsevier Ltd. All rights reserved.

  通过TiCl4/Et3SiD还原由醛与(1S,2S)-3,3,3-三氟-1-苯基丙烷-1,2-二醇9反应生成的乙缩醛，制备了具有高对映体过量的(1R)-1-氘醇。该手性助剂由L-苯乳酸开始，以消旋纯的形式合成。由于其苄基性质，它可轻易地从还原开环的1,3-二氧杂环戊烷产物中去除，从而得到所需的α-氘醇。© 2009 Elsevier Ltd. 保留所有权利。
• Hydrogen-Bonding Ability of Noyori–Ikariya Catalysts Enables Stereoselective Access to CF₃-Substituted <i>syn</i>-1,2-Diols via Dynamic Kinetic Resolution
  作者：Maša Sterle、Matej Huš、Matic Lozinšek、Anamarija Zega、Andrej Emanuel Cotman

  DOI：10.1021/acscatal.3c00980

  日期：2023.5.5

  vinyl, and alkyl ketones are tolerated, delivering products with ≥95% ee and ≥87:13 syn/anti. This methodology offers rapid access to stereopure bioactive molecules. Furthermore, DFT calculations for three types of Noyori–Ikariya ruthenium catalysts were performed to show their general ability of directing stereoselectivity via the hydrogen bond acceptor SO2 region and CH/π interactions.

  立体纯CF 3取代的顺式-1,2-二醇通过HCO 2 H/Et 3 N中相应外消旋α-羟基酮的还原动态动力学拆分来制备。 (Het)芳基、苄基、乙烯基和烷基酮是可耐受的，提供 ≥95% ee 和 ≥87:13 syn / anti的产品。这种方法可以快速获得立体纯的生物活性分子。此外，对三种类型的Noyori-Ikariya钌催化剂进行了DFT计算，以显示它们通过氢键受体SO 2区域和CH/π相互作用引导立体选择性的一般能力。