(3E)-2-methylhexa-3,5-dienoyl fluoride

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: (3E)-2-methylhexa-3,5-dienoyl fluoride
• 化学式: C₇H₉FO
• 分子量: 128.146
• InChiKey: GHXVZDQIMURFPX-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3E)-2-methylhexa-3,5-dienoyl fluoride 在 chiral substituted [1,3]dioxolane 、 (Bu₃Sn)O 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 2-甲基己-2,4-二烯酸
  参考文献：
  名称：

  Total synthesis of amphidinolide E and amphidinolide E stereoisomers

  摘要：

  Four amphidinolide E stereoisomers, amphidinolide E (1), 2-epi-amphidinolide E (2), 19-epi-amphidinolide E (3), and 2-epi-19-epi- amphidinolide E (4), have been synthesized via the judicious union of aldehyde 5, allylsilanes 7 or 8, acids 9 or 10, and vinylstannane 6. The C19 stereocenters of the C19 epimeric allylsilanes 7 and 8 were introduced via crotylboration reactions early in the synthesis. [3+2] Annulation reactions of aldehyde 5 with allylsilanes 7 and 8 were employed to set the core tetrahydrofuran units of 1-4. Finally, the C2 stereo-center was installed by esterification using acid 9, without incident, or with acid 10, in which case an unexpected and completely stereoselective inversion of C2 occurs. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.058

文献信息

• Total synthesis of amphidinolide E and amphidinolide E stereoisomers
  作者：Porino Va、William R. Roush

  DOI：10.1016/j.tet.2007.02.058

  日期：2007.6

  Four amphidinolide E stereoisomers, amphidinolide E (1), 2-epi-amphidinolide E (2), 19-epi-amphidinolide E (3), and 2-epi-19-epi- amphidinolide E (4), have been synthesized via the judicious union of aldehyde 5, allylsilanes 7 or 8, acids 9 or 10, and vinylstannane 6. The C19 stereocenters of the C19 epimeric allylsilanes 7 and 8 were introduced via crotylboration reactions early in the synthesis. [3+2] Annulation reactions of aldehyde 5 with allylsilanes 7 and 8 were employed to set the core tetrahydrofuran units of 1-4. Finally, the C2 stereo-center was installed by esterification using acid 9, without incident, or with acid 10, in which case an unexpected and completely stereoselective inversion of C2 occurs. (C) 2007 Elsevier Ltd. All rights reserved.