ethyl (E)-2,2-difluoro-3-hydroxy-4-hexenoate | 156544-69-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl (E)-2,2-difluoro-3-hydroxy-4-hexenoate
• 英文别名: ethyl (E)-2,2-difluoro-3-hydroxyhex-4-enoate
• CAS: 156544-69-3
• 化学式: C₈H₁₂F₂O₃
• 分子量: 194.178
• InChiKey: WROWHWZYZZBAGX-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  ethyl (E)-2,2-difluoro-3-hydroxy-4-hexenoate 在 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 15.17h， 生成 anti-(E)-5,5-difluoro-4-hydroxy-2,3-epoxydecan-6-one
  参考文献：
  名称：

  Synthesis of stereocontrolled α,α-difluoro-β-hydroxycarbonyl materials

  摘要：

  Synthesis and synthetic utilities of stereocontrolled alpha, alpha-di fluoro-beta-hydroxy-gamma,delta-unsaturated carbonyl compounds via enzymatic resolution with lipase PS (Pseudomonas cepacia, Amano Pharmaceutical Co. Ltd.) or lipase MY (Candida rugosa, Meito Sangyo Co. Ltd.) were described, and then the absolute configuration of obtained chiral materials was determined by the modified Mosher's method. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2004.09.026
• 作为产物：
  描述：

  巴豆醛 、 二氟溴乙酸乙酯 在 cerium(III) chloride 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以90%的产率得到ethyl (E)-2,2-difluoro-3-hydroxy-4-hexenoate
  参考文献：
  名称：

  An effective synthesis of 2,2-difluoro-3-hydroxy esters

  摘要：

  Reformatsky reactions of bromodifluoroacetate with carbonyl compounds and its applications to the synthesis of 2,2-difluoro-3-hydroxy esters as a means of two-carbon homologation with a difluoro moiety under mild conditions in good to excellent yields are described. In the case of aldehydes and aromatic ketones no catalyst was needed, while in the case of aliphatic ketones, 2 mol% of CeCl3 catalyst raises the yields dramatically from 30%-32% to 89%-92%.

  DOI：

  10.1016/0022-1139(93)02961-d

文献信息

• An effective synthesis of 2,2-difluoro-3-hydroxy esters
  作者：Yanchang Shen、Ming Qi

  DOI：10.1016/0022-1139(93)02961-d

  日期：1994.6

  Reformatsky reactions of bromodifluoroacetate with carbonyl compounds and its applications to the synthesis of 2,2-difluoro-3-hydroxy esters as a means of two-carbon homologation with a difluoro moiety under mild conditions in good to excellent yields are described. In the case of aldehydes and aromatic ketones no catalyst was needed, while in the case of aliphatic ketones, 2 mol% of CeCl3 catalyst raises the yields dramatically from 30%-32% to 89%-92%.
• Synthesis of stereocontrolled α,α-difluoro-β-hydroxycarbonyl materials
  作者：Takeshi Kaneda、Shinya Komura、Tomoya Kitazume

  DOI：10.1016/j.jfluchem.2004.09.026

  日期：2005.1

  Synthesis and synthetic utilities of stereocontrolled alpha, alpha-di fluoro-beta-hydroxy-gamma,delta-unsaturated carbonyl compounds via enzymatic resolution with lipase PS (Pseudomonas cepacia, Amano Pharmaceutical Co. Ltd.) or lipase MY (Candida rugosa, Meito Sangyo Co. Ltd.) were described, and then the absolute configuration of obtained chiral materials was determined by the modified Mosher's method. (C) 2004 Elsevier B.V. All rights reserved.