(+)-(R)-3,3,3-Trifluoro-1-propanol | 330-72-3

• 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)-3,3,3-Trifluoro-1-propanol
• 英文别名: (R)-1,1,1-trifluoro-2-hydroxy-3-phenylpropane；(R)-(+)-1-Phenyl-3,3,3-trifluoro-2-propanol；(R)-1,1,1-trifluoro-3-phenylpropan-2-ol；(R)-1,1,1-trifluoro-3-phenyl-2-propanol；(2R)-1,1,1-trifluoro-3-phenylpropan-2-ol
• CAS: 330-72-3；121960-72-3；108535-39-3
• 化学式: C₉H₉F₃O
• 分子量: 190.165
• InChiKey: UPFLNTYTTUCHQN-MRVPVSSYSA-N

物化性质

• 沸点：
  231.3±40.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2906299090

反应信息

• 作为产物：
  描述：

  1,1,1-三氟-3-苯基丙酮 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 甲酸 、 三乙胺 、 N-[(1S,2S)-2-氨基-1,2-二苯基乙基]-2,4,6-三(1-甲基乙基)苯亚磺酰胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (+)-(R)-3,3,3-Trifluoro-1-propanol
  参考文献：
  名称：

  使用新型手性Ru（II）-N-芳烃磺酰基-1,2-二苯基乙二胺配合物转移活化的酮

  摘要：

  使用新型手性N-芳烃磺酰基-1,2-二苯基乙二胺配体，在Ru催化的转移氢化作用下，一系列α-酮酯和α，α，α-三氟甲基酮被还原，收率高，对映选择性优异。

  DOI：

  10.1016/j.tetlet.2003.10.201

文献信息

• Unveiling the Hidden Performance of Whole Cells in the Asymmetric Bioreduction of Aryl-containing Ketones in Aqueous Deep Eutectic Solvents
  作者：Paola Vitale、Vincenzo Mirco Abbinante、Filippo Maria Perna、Antonio Salomone、Cosimo Cardellicchio、Vito Capriati

  DOI：10.1002/adsc.201601064

  日期：2017.3.20

  baker's yeast reduction of arylpropanones using deep eutectic solvents (DESs) as biodegradable and non‐hazardous co‐solvents. The nature of DES [e.g. choline chloride/glycerol (2:1)] and the percentage of water in the mixture proved to be critical for both the reversal of selectivity and to achieve high enantioselectivity on going from pure water (up to 98:2 er in favour of the S‐enantiomer) to DES/aqueous

  在这项贡献中，我们报道了使用深共熔溶剂（DESs）作为可生物降解和无害的共溶剂，成功地首次将贝克酵母还原为芳基丙烷。DES的性质[例如。氯化胆碱/甘油（2：1）]和混合物中水的百分比对于逆转选择性和从纯净水（达到98：2 er有利于S的萃取）实现高对映选择性都是至关重要的-对映体）到DES /水溶液混合物（最高达98：2 er的R对映体）。结果，通过简单地切换溶剂，就可以从相同的生物催化剂制备具有药用价值的手性醇的两种对映异构体。的一些可能的抑制（小号当DES用作助溶剂时，）氧化还原酶成为这种野生型全细胞生物催化剂基因组的一部分，可能为减少抗Prelog铺平道路。还讨论了针对一系列含芳基酮的这种生物转化的范围和局限性。
• 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。
• Homochiral Perfluoroalkyl-Group-Substituted Secondary Alcohols Through Stereoselective Reduction of Perfluoroalkyl 1-(<i>p</i>-Tolylsulfinyl)alkyl Ketones
  作者：Pierfrancesco Bravo、Massimo Frigerio、Giuseppe Resnati

  DOI：10.1055/s-1988-27764

  日期：——

  The reduction of some enantiomerically pure perfluoroalkyl α-(p-tolylsulfinyl) ketones was performed. Alcohols containing perfluoroalkyl and p-tolylsulfinyl groups were obtained with high diastereoselection when a phenyl residue was present on the sulfinylated carbon and with lower diastereoselection in the other cases. Removal of the chiral sulfinyl group from single diastereoisomers gave secondary alcohols containing a perfluoroalkyl group in enantiomerically pure form.

  对某些对映纯的全氟烷基 α-(对甲苯亚磺酰基)酮进行了还原。当亚磺酰基碳上存在苯基残基时，含有全氟烷基和对甲苯亚磺酰基的醇类具有高立体选择性，而在其他情况下具有较低立体选择性。从单一非对映异构体中去除手性亚磺酰基，得到含有全氟烷基的对映纯的仲醇。
• Screening on the use of Kluyveromyces marxianus CBS 6556 growing cells as enantioselective biocatalysts for ketone reductions
  作者：Paola Vitale、Filippo Maria Perna、Maria Grazia Perrone、Antonio Scilimati

  DOI：10.1016/j.tetasy.2011.11.014

  日期：2011.12

  The versatility of Kluyveromyces marxianus CBS 6556 growing cells in the enantioselective reduction of ketone functionalities to the corresponding alcohols was exploited. In particular, methyl ketones were reduced to (S)-alcohols with ees of up to 96%. Longer chain alkyl ketones afforded, under the same experimental condition, (R)-alcohols with an ee of up to 84%. Interestingly, carbon-carbon double and the triple bonds can also be reduced in the presence of Kluyveromyces marxianus CBS 6556 yeast. A cyclic ketone, such as 2-tetralone, was also quantitatively reduced to its corresponding (S)-alcohol with ee = 76%. (C) 2011 Elsevier Ltd. All rights reserved.
• Chiral Synthesis via Organoboranes. 40. Selective Reductions. 55. A Simple One-Pot Synthesis of the Enantiomers of Trifluoromethyloxirane. A General Synthesis in High Optical Purities of .alpha.-Trifluoromethyl Secondary Alcohols via the Ring-Cleavage Reactions of the Epoxide
  作者：P. Veeraraghavan Ramachandran、Baoqing Gong、Herbert C. Brown

  DOI：10.1021/jo00106a012

  日期：1995.1

  An extremely efficient one-pot asymmetric synthesis of either enantiomer of (trifluoramethyl)oxirane (3,3,3-trifluoro-1,2-epoxypropane, 4) in 64% yield and 96% ee has been achieved via the asymmetric reduction of the commercially available 1-bromo-3,3,3-trifluoro-2-propanone with either (+)- or (-)-B-chlorodiisopinocampheylborane (Aldrich: DIP-Chloride), followed by ring closure of the intermediate chloroborinate, IpcBCl[OCH(CH2Br)CF3]. The ring cleavage reactions of 4 provide a general synthesis of chiral trifluoromethyl carbinols without loss of optical activity. Thus we have synthesized 1-amino-3,3,3-trifluoro-2-propanol, 1-azido-3,3,3-trifluoro-2-propanol, 1-(diethylamino)3,3,3-trifluoro-2-propanol, 1-cyano-3,3,3-trifluoro-2-propanol, 1,1,1-trifluoro-2-propanol, 1,1,1-trifluoro-2-octanol, 1-phenyl-3,3,3-trifluoro-2-propanol, 1-ethoxy-3,3,3-trifluoro-2-propanol, and 1,2-dihydroxy-3,3,3-trifluorapropane, in 61-88% yields and in 96% ee by the cleavage of 4 with the appropriate nucleophile.