(R)-(+)-1,1,1-trifluoro-2-decanol | 108535-33-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (R)-(+)-1,1,1-trifluoro-2-decanol
• 英文别名: (R)-(+)-(1-trifluoromethyl)nonanol；(R)-1,1,1-Trifluorodecan-2-ol；(2R)-1,1,1-trifluorodecan-2-ol
• CAS: 108535-33-7
• 化学式: C₁₀H₁₉F₃O
• 分子量: 212.255
• InChiKey: FZHCYMPYGWJDQU-SECBINFHSA-N

物化性质

• 沸点：
  233.6±35.0 °C(Predicted)
• 密度：
  1.021±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(+)-1,1,1-trifluoro-2-decanol 在 吡啶 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 4-[[hydroxy-[(2R)-1,1,1-trifluorodecan-2-yl]oxyphosphoryl]methyl]benzoic acid
  参考文献：
  名称：

  Stereoselective synthesis of fluorinated materials catalyzed by an antibody

  摘要：

  A monoclonal antibody, elicited by a transition-state analogue for the hydrolysis of fluorinated esters, acted as an enzymelike catalyst for the preparation of chiral fluorinated compounds. The syntheses of (R)- or (S)-1-(fluoroalkyl)alkanols and an allylic alcohol possessing a trifluoromethyl group in high optical purity (> 98% enantiomeric excess (ee)) by antibody-derived reagents are described. The role of molecular recognition by antibody reagents and its importance to the preparation of optically pure materials is described. Significantly, it has been found that a fluoromethyl group on the stereogenic center or an acyloyl group enhanced the optical purity of the resultant products.

  DOI：

  10.1021/ja00006a032
• 作为产物：
  描述：

  (+)-1,1,1-trifluoro-2-decanol 生成 (R)-(+)-1,1,1-trifluoro-2-decanol
  参考文献：
  名称：

  Highly enantioselective synthesis of long chain alkyl trifluoromethyl carbinols and β-thiotrifluoromethyl carbinols through lipases

  摘要：

  Among a variety of lipases tested, Candida antarctica lipase has been found to promote the enantioselective acylation of long chain alkyl trifluoromethyl carbinols 1a-4a and beta-thiotrifluoromethyl carbinols 5a-7a, producing both R and S enantiomeric alcohols in good to excellent chemical yield and enantioselectivity. In all cases the lipase preferentially acylates the S enantiomer, irrespective the presence or not of a sulfur atom in beta position to the hydroxyl group, When the reaction was carried out on the non-fluorinated substrates 1c-2c, the process occurred much faster and with higher e.e. of the less reacting enantiomer than when conducted on the fluorinated substrates. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00256-x

文献信息

• Liquid crystal compound
  申请人：Showa Shell Sekiyu Kabushiki Kaisha

  公开号：US05207947A1

  公开（公告）日：1993-05-04

  Liquid crystal compound of the formula ##STR1## wherein R.sub.1 and R.sub.2 each is a C.sub.1-18 alkyl group or an aralkyl group, R' is a haloalkyl group, X is --0--, --CO--, --COO-- or direct bond, Y is --COO--, --OCO-- or --CH.sub.2 O--, (A) and (B) each is ##STR2## and p and l each is zero or one.

  液晶化合物的公式为##STR1##，其中R1和R2各自是C1-18烷基或芳烷基，R'是卤代烷基，X是-0-，-CO-，-COO-或直接键，Y是-COO-，-OCO-或-CH2O-，（A）和（B）各自是##STR2##，p和l各自是零或一。
• Chiral synthesis via organoboranes. 38. Selective reductions. 48. Asymmetric reduction of trifluoromethyl ketones by B-chlorodiisopinocampheylborane in high enantiomeric purity
  作者：P. Veeraraghavan Ramachandran、Aleksandar V. Teodorovic'、Herbert C. Brown

  DOI：10.1016/s0040-4020(01)80530-5

  日期：1993.2

  respectively. The reagent reduces alkyl trifluoromethyl ketones at a rate faster than that of the aryl derivatives, while still providing the product alcohols in very high ee. Thus, 1,1,1-trifluoroacetone, 1,1,1-trifluorononan-2-one, and 1,1,1-trifluorodecan-2-one are all reduced within 4–8 h in 89% ee, 92% ee, and 91% ee, respectively. Even α-sec-alkyl trifluoromethyl ketones are handled by 1 very efficiently

  我们几年前引入的（-）- B-氯二异辛基硼烷[（-）-DIP-Chloride TM，1 ]在非常高的ee中显示可以将前手性芳基和烷基全氟酮还原为相应的旋光性醇。例如，2,2,2-三氟苯乙酮，三氟乙酰基-1-萘和三氟乙酰基-2-萘在室温下rt分别在90％ee，78％ee和91％ee中被1还原。通过从戊烷中结晶出最初形成的产物，可将1-苯基-2,2,2-三氟乙醇的光学纯度提高到≥99％ee。1,1,2,2,2-五氟苯乙酮和1,1,2,2,3,3,3，-七氟丁苯酮在3 d内还原为1分别对应于92％ee和87％ee的醇。该试剂以比芳基衍生物更快的速率还原烷基三氟甲基酮，同时仍以非常高的ee提供产物醇。因此，在89％ee，92％ee中，1,1,1-三氟丙酮，1,1,1-三氟壬二-2-酮和1,1,1-三氟癸-2-酮均在4-8小时内还原和分别为ee的91％。即使α-仲烷基三氟甲基酮也非常有效地被1处理
• Enantioselective Rhodium(I)-Catalyzed Hydrogenation of Trifluoromethyl Ketones
  作者：Yoshichika Kuroki、Yuko Sakamaki、Katsuhiko Iseki

  DOI：10.1021/ol006962s

  日期：2001.2.1

  [figure: see text] The asymmetric hydrogenation of trifluoromethyl ketones to yield chiral alpha-trifluoromethyl alcohols with enantiomeric excesses up to 98% was achieved in the presence of chiral rhodium-(amidephosphine-phosphinite) complexes.

  在手性铑-（酰胺膦-次膦酸酯）配合物的存在下，三氟甲基酮的不对称氢化反应产生对映体过量高达98％的手性α-三氟甲基醇。
• Synthetic approach to stereoisomers of allylic alcohols possessing a trifluoromethyl group
  作者：Tomoya Kitazume、Jeng Tain Lin、Takashi Yamazaki、Mitsunori Takeda

  DOI：10.1016/s0022-1139(00)82938-3

  日期：1989.5

  A number of stereoisomers of optically pure allylic alcohols with a trifluoromethyl group [CF3CH(OH)CH=CHR : R=Ph. C6H13] were prepared, utilizing the enantiotopic specificity of asymmetric hydrolysis of their acetates by hydrolases. Their absolute configurations were determined.

  具有三氟甲基的光学纯的烯丙基醇的许多立体异构体[CF 3 CH（OH）CH ＝ CHR：R ＝ Ph。利用水解酶的乙酸盐的不对称水解的对映体特异性，制备了C 6 H 13 ]。确定了它们的绝对构型。
• Enantioselective reduction of fluoroalkyl alkynyl ketones: Enormous electronic effect of the trifluoromethyl group.
  作者：Yuji Hanzawa、Kei-ichi Kawagoe、Yoshiro Kobayashi

  DOI：10.1248/cpb.35.2609

  日期：——

  Fluoroalkyl alkynyl ketones (1a-c) were reduced enantioselectively by (R) -BINAL-H and (S) -Alpine-Borane to give optically active alcohols (2a-c). In the BINAL-H reduction, the trifluoromethyl group exerted an electronic effect on the enantioselectivity of the reagent.

  氟烷基炔基酮（1a-c）通过（R）-BINAL-H和（S）-Alpine-Borane进行对映选择性还原，得到具有光学活性的醇（2a-c）。在BINAL-H还原反应中，三氟甲基对试剂的对映选择性产生电子效应。