(R)-ethyl 4-(4-chlorophenyl)-2-hydroxy-2-(trifluoromethyl) pent-4-enoate | 1071629-28-1

• 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: (R)-ethyl 4-(4-chlorophenyl)-2-hydroxy-2-(trifluoromethyl) pent-4-enoate
• 英文别名: 4-(4-chloro-phenyl)-2-hydroxy-2-trifluoromethyl-pent-4-enoic acid ethyl ester；ethyl (2R)-4-(4-chlorophenyl)-2-hydroxy-2-trifluoromethylpent-4-enoate；ethyl (2R)-4-(4-chlorophenyl)-2-hydroxy-2-(trifluoromethyl)pent-4-enoate
• CAS: 1071629-28-1
• 化学式: C₁₄H₁₄ClF₃O₃
• 分子量: 322.712
• InChiKey: GTVHJZINPRMUJJ-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对氯甲基苯乙烯 、 3,3,3-三氟丙酮酸乙酯 在 C₃₅H₂₅F₃NO₇PS 作用下， 以 邻二甲苯 为溶剂， 以55%的产率得到(R)-ethyl 4-(4-chlorophenyl)-2-hydroxy-2-(trifluoromethyl) pent-4-enoate
  参考文献：
  名称：

  与强酸性手性布朗斯台德酸的高对映选择性有机催化羰基-烯反应，可作为有效的催化剂。

  摘要：

  DOI：

  10.1002/anie.200802139

文献信息

• Asymmetric carbonyl-ene reaction of trifluoropyruvate catalyzed by Pd(II)-SunPhos complex
  作者：Lili Jiang、Bei Hu、Xiaomin Xie、Zhaoguo Zhang

  DOI：10.1016/j.tet.2017.10.044

  日期：2017.12

  An efficient asymmetric carbonyl-ene reaction of trifluoropyruvate catalyzed by chiral Pd(II)/(S)-SunPhos complex was developed. A series of optically active homoallylic alcohols containing a CF3 group were obtained with high yields and excellent ee under mild conditions. Particularly, the reaction of isobutylene and trifluoropyruvate gave the desired product (90% yield, 98% ee) with catalyst loading

  开发了一种有效的手性Pd（II）/（S）-SunPhos配合物催化的三氟丙酮酸不对称羰基-烯反应。在温和条件下以高收率和优异的ee获得了一系列包含CF 3基团的光学活性均烯丙基醇。特别地，异丁烯和三氟丙酮酸酯的反应得到所需产物（90％收率，98％ee），催化剂在二氯乙烷/甲苯中的负载量低至0.01mol％。
• Asymmetric carbonyl-ene and Friedel–Crafts reactions catalysed by Lewis acid platinum group metal complexes of the enantiopure atropisomeric biaryl-like diphosphine (S)-Me2-CATPHOS: a comparison with BINAP
  作者：Simon Doherty、Julian G. Knight、Hamid Mehdi-Zodeh

  DOI：10.1016/j.tetasy.2012.01.022

  日期：2012.2

  Lewis acid platinum and palladium complexes of (S)-Me-2-CATPHOS catalyse the carbonyl-ene reaction between allylbenzene derivatives and ethyl trifluoropyruvate to give the expected alpha-hydroxy esters with ee's up to 97%, while the corresponding reaction involving 2-allylfuran and thiophene was exclusively selective for Friedel-Crafts-type reactivity and gave the corresponding 2-hydroxy-trifluoromethyl ethyl esters in good yield and moderate to good enantioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.
• Highly Enantioselective Organocatalytic Carbonyl-Ene Reaction with Strongly Acidic, Chiral Brønsted Acids as Efficient Catalysts
  作者：Magnus Rueping、Thomas Theissmann、Alexander Kuenkel、René M. Koenigs

  DOI：10.1002/anie.200802139

  日期：2008.8.25