(E)-tert-butyl 5-phenylpent-3-enoate | 1443734-83-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-tert-butyl 5-phenylpent-3-enoate
• 英文别名: tert-butyl (E)-5-phenylpent-3-enoate
• CAS: 1443734-83-5
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: GQOUZNDSBHAVAS-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-tert-butyl 5-phenylpent-3-enoate 在 4-乙酰氨基苯磺酰叠氮 、 silver(I) acetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 triethylamine tris(hydrogen fluoride) 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 (E)-tert-butyl 4-fluoro-5-phenylpent-2-enoate
  参考文献：
  名称：

  Silver-Catalyzed Vinylogous Fluorination of Vinyl Diazoacetates

  摘要：

  A silver-catalyzed vinylogous fluorination of vinyl diazoacetates to generate gamma-fluoro-alpha,beta-unsaturated carbonyls is presented. Application of this method to the fluorination of farnesol and steroid derivatives was achieved.

  DOI：

  10.1021/ol403017e
• 作为产物：
  描述：

  potassium trans-3-phenyl-1-propen-1-yltrifluoroborate 、 氯乙酸叔丁酯 在 XPhos Pd G2 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以66%的产率得到(E)-tert-butyl 5-phenylpent-3-enoate
  参考文献：
  名称：

  Pd-Catalyzed Cross-Coupling of Potassium Alkenyltrifluoroborates with 2-Chloroacetates and 2-Chloroacetamides

  摘要：

  A protocol for the stereocontrolled synthesis of (E)- and (Z)-beta,gamma-unsaturated esters and amides is reported. 2-Chloroacetates as well as secondary and tertiary 2-chloroacetamides were successfully employed as electrophiles in the Suzuki-Miyaura cross-coupling reaction with potassium (E)- and (Z)-alkenyltrifluoroborates, affording the corresponding products in high yield.

  DOI：

  10.1021/ol401377q

文献信息

• Silver-Catalyzed Vinylogous Fluorination of Vinyl Diazoacetates
  作者：Changming Qin、Huw M. L. Davies

  DOI：10.1021/ol403017e

  日期：2013.12.20

  A silver-catalyzed vinylogous fluorination of vinyl diazoacetates to generate gamma-fluoro-alpha,beta-unsaturated carbonyls is presented. Application of this method to the fluorination of farnesol and steroid derivatives was achieved.
• Pd-Catalyzed Cross-Coupling of Potassium Alkenyltrifluoroborates with 2-Chloroacetates and 2-Chloroacetamides
  作者：Gary A. Molander、Thiago Barcellos、Kaitlin M. Traister

  DOI：10.1021/ol401377q

  日期：2013.7.5

  A protocol for the stereocontrolled synthesis of (E)- and (Z)-beta,gamma-unsaturated esters and amides is reported. 2-Chloroacetates as well as secondary and tertiary 2-chloroacetamides were successfully employed as electrophiles in the Suzuki-Miyaura cross-coupling reaction with potassium (E)- and (Z)-alkenyltrifluoroborates, affording the corresponding products in high yield.