ethyl (2Z,4E,6Z)-7-fluoro-8-hydroxyl-3-methyl-2,4,6-octatrienoate | 173938-01-7

• 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,6Z)-7-fluoro-8-hydroxyl-3-methyl-2,4,6-octatrienoate
• 英文别名: ethyl (2Z,4E,6Z)-7-fluoro-8-hydroxy-3-methylocta-2,4,6-trienoate
• CAS: 173938-01-7
• 化学式: C₁₁H₁₅FO₃
• 分子量: 214.237
• InChiKey: HKNNDFKUNMJDKD-SCHZRKRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2Z,4E,6Z)-7-fluoro-8-hydroxyl-3-methyl-2,4,6-octatrienoate 在 manganese(IV) oxide 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.05h， 以75%的产率得到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
• 作为产物：
  描述：

  (Z)-3-iodo-but-2-enoic acid ethyl ester 在 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 0.83h， 生成 ethyl (2Z,4E,6Z)-7-fluoro-8-hydroxyl-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.