(E)-(R)-2-methylhexa-3,5-dienoic acid | 921763-61-3

• 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)-(R)-2-methylhexa-3,5-dienoic acid
• 英文别名: (2R,3E)-2-methylhexa-3,5-dienoic acid
• CAS: 921763-61-3
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: BFNAVDGAMZHSKZ-BMMSZFGTSA-N

物化性质

• 沸点：
  233.6±9.0 °C(Predicted)
• 密度：
  0.987±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-(R)-2-methylhexa-3,5-dienoic acid 在 chiral substituted [1,3]dioxolane 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 三乙胺 作用下， 以 四氢呋喃 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
• 作为产物：
  描述：

  (4R,5S)-4-methyl-3-((E)-(R)-2-methyl-hexa-3,5-dienoyl)-5-phenyl-oxazolidin-2-one 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 以64%的产率得到(E)-(R)-2-methylhexa-3,5-dienoic acid
  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

• Enantioselective Synthesis of the 1,3‐Dienyl‐5‐Alkyl‐6‐Oxy Motif: Method Development and Total Synthesis
  作者：Jie Wang、Chuning Guo、Yaqian Liu、Yunpeng Ji、Hongli Jia、Houhua Li

  DOI：10.1002/anie.202400478

  日期：2024.4.8

  Method development and total synthesis have resulted in the enantioselective synthesis of the 1,3-dienyl-5-alkyl-6-oxy motif, and thus expedient total syntheses of three types of natural products (glutarimide antibiotics, α-pyrone polyketides and Lupin alkaloids), completed within 4–7 steps.

  方法开发和全合成实现了1,3-二烯基-5-烷基-6-氧基的对映选择性合成，从而方便地全合成了三种天然产物（戊二酰亚胺抗生素、α-吡喃酮聚酮化合物和羽扇豆生物碱） ），在 4-7 个步骤内完成。
• 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.