methyl (R,E)-5-iodo-2-methylpent-4-enoate | 1259286-24-2

• 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: methyl (R,E)-5-iodo-2-methylpent-4-enoate
• 英文别名: 4-Pentenoic acid, 5-iodo-2-methyl-, methyl ester, (2R,4E)-；methyl (E,2R)-5-iodo-2-methylpent-4-enoate
• CAS: 1259286-24-2
• 化学式: C₇H₁₁IO₂
• 分子量: 254.068
• InChiKey: YPPRCBOSWMCWRU-MXTDHUQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  10.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (S)-4-benzyl-3-((R)-2-methylpent-4-ynoyl)oxazolidin-2-one 在 Schwartz's reagent 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 3.37h， 生成 methyl (R,E)-5-iodo-2-methylpent-4-enoate
  参考文献：
  名称：

  Stereocontrolled Total Syntheses of Isodomoic Acids G and H via a Unified Strategy

  摘要：

  Marine neuroexcitatory compounds isodomoic acids G and H were efficiently synthesized from a common intermediate using a silicon-based cross-coupling reaction. Dividing each target compound into the core fragment and the side-chain fragment enabled the synthesis to be convergent. The trans-2,3-disubstituted pyrrolidine core fragment was accessed through a diastereoselective rhodium-catalyzed carbonylative silylcarbocyclization reaction of a vinylglycine-derived 1,6-enyne. A stereochemically divergent desilylative iodination reaction was developed to convert the cyclization product to both E- and Z-alkenyl iodides, which would eventually lead to isodomoic acid G and isodomoic acid H, respectively. The late-stage alkenyl alkenyl silicon-based cross-coupling reaction uniting the core alkenyl iodides and the side-chain alkenylsilanol was achieved under mild conditions. Finally, two mild deprotections afforded the target molecules.

  DOI：

  10.1021/jo101790z