ethyl (2Z,4E,6E)-7-fluoro-8-oxo-3-methyl-2,4,6-octatrienoate | 173864-84-1

• 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: ethyl (2Z,4E,6E)-7-fluoro-8-oxo-3-methyl-2,4,6-octatrienoate
• 英文别名: ethyl (2Z,4E,6Z)-7-fluoro-3-methyl-8-oxoocta-2,4,6-trienoate
• CAS: 173864-84-1
• 化学式: C₁₁H₁₃FO₃
• 分子量: 212.221
• InChiKey: LRWGLTVHDXHNIQ-SCHZRKRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  beta-环香叶基三苯基鏻溴化物 、 ethyl (2Z,4E,6E)-7-fluoro-8-oxo-3-methyl-2,4,6-octatrienoate 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 ethyl (2Z,4E,6Z,8Z)-7-fluoro-3-methyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoate 、 ethyl (2Z,4E,6Z,8E)-7-fluoro-3-methyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoate
  参考文献：
  名称：

  Stereoselective synthesis of 9-trans-9-Desmethyl-9-fluororetinals based on the four-components coupling approach

  摘要：

  9-trans-9-Desmethyl-9-fluororetinal analogs were synthesized by the four-components coupling approach. Horner-Emmons olefination of 3 afforded the undesired 2E-isomer 5 which was transformed to 6E-triene 8 via the Stille coupling reaction. Isomerization of 6E-triene 8 with an iodine catalyst proceeded in a highly regioselective manner to give the 6Z-isomer 9. Wittig reaction of 13 derived from oxidation of 9 followed by reduction and oxidation provided 13-cis-9-desmethyl-9-fluororetinal 17. The 13-cis-analog 17 was regioselectively converted to the all-trans-isomer 19 by treatment with trifluoroacetic acid. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01175-2
• 作为产物：
  描述：

  (Z)-3-iodo-but-2-enoic acid ethyl ester 在 manganese(IV) oxide 、 双(乙腈)氯化钯(II) 、 碘 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.88h， 生成 ethyl (2Z,4E,6E)-7-fluoro-8-oxo-3-methyl-2,4,6-octatrienoate
  参考文献：
  名称：

  Stereoselective synthesis of 9-trans-9-Desmethyl-9-fluororetinals based on the four-components coupling approach

  摘要：

  9-trans-9-Desmethyl-9-fluororetinal analogs were synthesized by the four-components coupling approach. Horner-Emmons olefination of 3 afforded the undesired 2E-isomer 5 which was transformed to 6E-triene 8 via the Stille coupling reaction. Isomerization of 6E-triene 8 with an iodine catalyst proceeded in a highly regioselective manner to give the 6Z-isomer 9. Wittig reaction of 13 derived from oxidation of 9 followed by reduction and oxidation provided 13-cis-9-desmethyl-9-fluororetinal 17. The 13-cis-analog 17 was regioselectively converted to the all-trans-isomer 19 by treatment with trifluoroacetic acid. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01175-2

文献信息

• Stereoselective synthesis of 9-trans-9-Desmethyl-9-fluororetinals based on the four-components coupling approach
  作者：Tetsuro Shinada、Noriko Sekiya、Nina Bojkova、Kazuo Yoshihara

  DOI：10.1016/s0040-4020(98)01175-2

  日期：1999.3

  9-trans-9-Desmethyl-9-fluororetinal analogs were synthesized by the four-components coupling approach. Horner-Emmons olefination of 3 afforded the undesired 2E-isomer 5 which was transformed to 6E-triene 8 via the Stille coupling reaction. Isomerization of 6E-triene 8 with an iodine catalyst proceeded in a highly regioselective manner to give the 6Z-isomer 9. Wittig reaction of 13 derived from oxidation of 9 followed by reduction and oxidation provided 13-cis-9-desmethyl-9-fluororetinal 17. The 13-cis-analog 17 was regioselectively converted to the all-trans-isomer 19 by treatment with trifluoroacetic acid. (C) 1999 Elsevier Science Ltd. All rights reserved.