2,2-difluoro-3-hydroxy-5-phenylpent-4-enoic acid ethyl ester | 194421-06-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: 2,2-difluoro-3-hydroxy-5-phenylpent-4-enoic acid ethyl ester
• 英文别名: ethyl (4E)-2,2-difluoro-3-hydroxy-5-phenylpent-4-enoate；ethyl (E)-2,2-difluoro-3-hydroxy-3-phenylpent-4-enoate；ethyl (E)-2,2-difluoro-3-hydroxy-5-phenylpent-4-enoate
• CAS: 194421-06-2
• 化学式: C₁₃H₁₄F₂O₃
• 分子量: 256.249
• InChiKey: QMKDKADLECGAOV-CMDGGOBGSA-N

物化性质

• 沸点：
  393.0±42.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-difluoro-3-hydroxy-5-phenylpent-4-enoic acid ethyl ester 在 sodium tetrahydroborate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.42h， 生成 (E)-7-phenyl-3,5-dihydroxy-4,4-difluoro-6-heptenoic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of γ,γ-difluoro-β-hydroxy-δ-lactones as new precursors of HMG-CoA reductase inhibitor

  摘要：

  A series of gamma,gamma-difluoro-beta-hydroxy-delta-lactones 1 were efficiently synthesized as new precursors of HMG-CoA reductase inhibitor in one pot by treatment of readily prepared gem-difluoromethylenated acetonides 3 with trifluoroacetic acid. Contrarily, acetonides 3 could be transformed to the gamma,gamma-gem-difluoromethylenated alpha,beta-unsaturated delta-lactones 2 through hydrolyzation and lactonization in refluxing toluene. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.09.014
• 作为产物：
  描述：

  反式肉桂醛 、 2-（三甲基硅基）-2，2-二氟乙酸乙酯 在 1,3-双(2,6-二异丙基苯基)咪唑-2-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以77%的产率得到2,2-difluoro-3-hydroxy-5-phenylpent-4-enoic acid ethyl ester
  参考文献：
  名称：

  醛与N-杂环卡宾催化的氟化甲硅烷基-Reformatsky反应

  摘要：

  N-杂环卡宾（NHC）已被用作羰基化合物的氟化甲硅烷基-Reformatsky反应的高效有机催化剂。在5-10 mol％的NHC A存在下，各种醛和2,2,2-三氟苯乙酮与乙酸二氟（三甲基硅烷基）酯反应生成β-羟基宝石-二氟酯，产率为20-96％。

  DOI：

  10.1016/j.tet.2017.06.027

文献信息

• Synthesis of γ-fluoroalkylated allylic amines derivatives via palladium-catalyzed Overman rearrangement
  作者：Xin-Yi Jiang、Lingling Chu、Ruo-Wen Wang、Feng-Ling Qing

  DOI：10.1016/j.tetlet.2012.10.045

  日期：2012.12

  A Pd-catalyzed Overman rearrangement of α-fluoroalkylated allylic trichloroacetimidates has been developed. This reaction allows for an efficient synthesis of γ-fluoroalkylated allylic amine derivatives with excellent regio- and stereo-selectivities under mild conditions.

  已经开发了α-氟烷基化的烯丙基三氯乙亚氨酸酯的Pd催化的超载重排。该反应允许在温和条件下有效合成具有优异的区域选择性和立体选择性的γ-氟代烷基化的烯丙基胺衍生物。
• Asymmetric aldol addition of aldehydes to a difluoroketene silyl acetal catalyzed by chiral Lewis acids
  作者：Katsuhiko Iseki、Yoshichika Kuroki、Daisuke Asada、Mie Takahashi、Satoshi Kishimoto、Yoshiro Kobayashi

  DOI：10.1016/s0040-4020(97)00683-2

  日期：1997.7

  substoichiometric amount of chiral Lewis acid 2 or 3 provides the corresponding α,α-difluoro β-hydroxy esters 4–12 with high enantioselectivities (up to 98% ee). Reaction temperature has a great influence on the enantiofacial selection of aldehydes; the reactions of benzyloxyacetaldehyde catalyzed by Lewis acid 2 at −78 and −30°C gave the (+)- and (−)-α,α-difluoro β-hydroxy esters 7 in optical yields of 98% and

  在亚化学计量的手性路易斯酸2或3的存在下，醛与二氟乙烯乙基三甲基甲硅烷基乙缩醛的醛醇缩合反应（1）提供相应的具有高对映选择性（高达98％ee的α，α-二氟β-羟基酯4-12））。反应温度对醛的对面选择有很大的影响。路易斯酸2在-78和-30℃下催化苄氧基乙醛的反应，分别得到（+）-和（-）-α，α-二氟β-羟基酯7，其光学收率分别为98％和85％。
• Palladium-catalyzed arylation of α,α-difluoro-allylic-β-hydroxyester
  作者：Xiang Fang、Xueyan Yang、Xianjin Yang、Min Zhao、Guorong Chen、Fanhong Wu

  DOI：10.1016/j.tetlet.2006.09.111

  日期：2006.11

  The aryl-substituted alpha,alpha-difluoro-allylic-beta-hydroxyesters and aryl-substituted alpha,alpha-difluoroketones were obtained via the coupling reaction of aryl iodides with alpha,alpha-difluoro-allylic-beta-hydroxyester in the presence of Pd(OAc)(2) as the catalyst and Et3N as the base. (c) 2006 Elsevier Ltd. All rights reserved.
• Kinetic resolution of 2,2-difluoro-3-hydroxy-3-aryl-propionates catalyzed by organocatalyst (R)-benzotetramisole
  作者：Hui Zhou、Qing Xu、Peiran Chen

  DOI：10.1016/j.tet.2008.04.055

  日期：2008.6

  Kinetic resolution of a series of ethyl 2,2-difluoro-3-hydroxy-3-aryl-propionates catalyzed by (R)-benzotetramisole has been performed. It was found that when the aryl group was phenyl or phenyl substituted with electron-donating group (such as -Me, -OMe, and -SMe) or naphthyl groups, the enantio-selectivity factor (s) could reach 20 or higher; electron-withdrawing (such as fluorine) substitution on the benzene ring dramatically lowers the s value. Kinetic resolution in preparative scale for some of the substrates demonstrated the applicability of this method. (c) 2008 Elsevier Ltd. All rights reserved.
• LINDERMAN, RUSSELL J.;GRAVES, DAVID M., J. ORG. CHEM., 54,(1989) N, C. 661-668
  作者：LINDERMAN, RUSSELL J.、GRAVES, DAVID M.

  DOI：——

  日期：——