(S)-1,1,1-trifluoro-2-phenylbut-3-ene-2-ol | 152141-78-1

• 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: (S)-1,1,1-trifluoro-2-phenylbut-3-ene-2-ol
• 英文别名: (2S)-1,1,1-trifluoro-2-phenylbut-3-en-2-ol
• CAS: 152141-78-1
• 化学式: C₁₀H₉F₃O
• 分子量: 202.176
• InChiKey: QZTXJLLJGFCKCH-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (S)-1,1,1-trifluoro-2-phenylbut-3-ene-2-ol 在 二甲基硫 、 臭氧 、 sodium chlorite 、 天然橡胶 作用下， 以 甲醇 、 叔丁醇 为溶剂， 以87%的产率得到(R)-3,3,3-trifluoro-2-hydroxy-2-phenylpropanoic acid
  参考文献：
  名称：

  三氟甲基酮的催化对映选择性烯基化和苯基化

  摘要：

  描述了三氟甲基酮的催化对映选择性烯基化和苯基化。使用CuF–DTBM-SEGPHOS络合物作为催化剂（5–10 mol％）和烯基硅烷作为亲核试剂，在芳基三氟甲基酮的烯基化反应中产生高对映选择性（高达84％ee）。这是三氟甲基酮催化对映选择性烯基化的第一个例子。该产品是通用的手性结构单元，其中包含三氟甲基取代的叔醇部分。

  DOI：

  10.1016/j.tetlet.2006.09.048
• 作为产物：
  描述：

  (R)-4,4,4-trifluoro-3-phenyl-3-hydroxybutyne 在 Lindlar's catalyst 喹啉 、 氢气 作用下， 以 正戊烷 为溶剂， 以83%的产率得到(S)-1,1,1-trifluoro-2-phenylbut-3-ene-2-ol
  参考文献：
  名称：

  The synthesis of (R)-γ-phenyl-γ-(trifluoromethyl)-butyrolactone and (2R,3S)-1,1,1-trifluoro-2-methoxy-2-phenyl-3,4-epoxybutane in homochiral forms.

  摘要：

  (R)-gamma-Phenyl-gamma-(trifluoromethyl)-butyrolactone (1) and (2R,3S)-1,1,1-trifluoro-2-methoxy-2-phenyl-3,4-epoxybutane (2) have been prepared in high optical purity from the tertiary (S)-(3)-acetate which was resolved using the lipase from Candida cylindracea.

  DOI：

  10.1016/s0957-4166(00)80378-x

文献信息

• Characterization of a novel esterase isolated from intertidal flat metagenome and its tertiary alcohols synthesis
  作者：Ki-Hoon Oh、Giang-Son Nguyen、Eun-Young Kim、Robert Kourist、Uwe Bornscheuer、Tae-Kwang Oh、Jung-Hoon Yoon

  DOI：10.1016/j.molcatb.2012.04.015

  日期：2012.8

  A gene coding for an esterase (EstEH112) was isolated from metagenome originated from Korean intertidal flat sediment. The putative esterase gene encoded a 340 amino acids protein with characteristic residues of lipolytic enzymes such as a conserved pentapeptide (GXSXG), the typical catalytic S-D-H triad, and a GGG(A)X-motif in the oxyanion hole near the active site similar to the hormone sensitive lipase (HSL) family. p-Nitrophenyl butyrate was the best substrate for the enzyme among the other p-nitrophenyl esters investigated. The apparent optimal temperature and pH for EstEH112 was 35 C and at pH 8.0, respectively. EstEH112 efficiently catalyzed the hydrolysis of various large tertiary alcohol esters. These characteristics of EstEH112 make it a potential candidate for application in biocatalysis. (C) 2012 Elsevier B.V. All rights reserved.
• The synthesis of (R)-γ-phenyl-γ-(trifluoromethyl)-butyrolactone and (2R,3S)-1,1,1-trifluoro-2-methoxy-2-phenyl-3,4-epoxybutane in homochiral forms.
  作者：David O'Hagan、Naveed A. Zaidi、R.Brian Lamont

  DOI：10.1016/s0957-4166(00)80378-x

  日期：1993.7

  (R)-gamma-Phenyl-gamma-(trifluoromethyl)-butyrolactone (1) and (2R,3S)-1,1,1-trifluoro-2-methoxy-2-phenyl-3,4-epoxybutane (2) have been prepared in high optical purity from the tertiary (S)-(3)-acetate which was resolved using the lipase from Candida cylindracea.
• Catalytic enantioselective alkenylation and phenylation of trifluoromethyl ketones
  作者：Rie Motoki、Daisuke Tomita、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1016/j.tetlet.2006.09.048

  日期：2006.11

  Catalytic enantioselective alkenylation and phenylation of trifluoromethyl ketones are described. High enantioselectivity (up to 84% ee) was produced in an alkenylation of aryl trifluoromethyl ketones using a CuF–DTBM-SEGPHOS complex as the catalyst (5–10 mol %) and alkenylsilanes as the nucleophile. This is the first example of catalytic enantioselective alkenylation of trifluoromethyl ketones. The

  描述了三氟甲基酮的催化对映选择性烯基化和苯基化。使用CuF–DTBM-SEGPHOS络合物作为催化剂（5–10 mol％）和烯基硅烷作为亲核试剂，在芳基三氟甲基酮的烯基化反应中产生高对映选择性（高达84％ee）。这是三氟甲基酮催化对映选择性烯基化的第一个例子。该产品是通用的手性结构单元，其中包含三氟甲基取代的叔醇部分。