ethyl (4E)-2,2-difluoro-3-hydroxy-5-(4-methoxyphenyl)pent-4-enoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: ethyl (4E)-2,2-difluoro-3-hydroxy-5-(4-methoxyphenyl)pent-4-enoate
• 英文别名: ethyl (E)-2,2-difluoro-3-hydroxy-5-(4-methoxyphenyl)pent-4-enoate
• 化学式: C₁₄H₁₆F₂O₄
• 分子量: 286.275
• InChiKey: LKOFPAYJHIRHDG-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (4E)-2,2-difluoro-3-hydroxy-5-(4-methoxyphenyl)pent-4-enoate 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 tert-butyl (E)-4,4-difluoro-3,5-dihydroxy-7-(4-methoxyphenyl)hept-6-enoate
  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：

  4-甲氧基肉桂醛 、 二氟溴乙酸乙酯 在 锌 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl (4E)-2,2-difluoro-3-hydroxy-5-(4-methoxyphenyl)pent-4-enoate
  参考文献：
  名称：

  通过钯催化的超人重排合成γ-氟烷基化的烯丙基胺衍生物

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2012.10.045

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。
• 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.
• Synthesis of γ,γ-difluoro-β-hydroxy-δ-lactones as new precursors of HMG-CoA reductase inhibitor
  作者：Xiaoguang Wang、Xiang Fang、Hongyuan Xiao、Yan Yin、Huimin Xia、Fanhong Wu

  DOI：10.1016/j.jfluchem.2011.09.014

  日期：2012.1

  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.