(2E,3E)-2-ethylidene-4-iodopent-3-enoic acid methyl ester | 853335-59-8

• 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: (2E,3E)-2-ethylidene-4-iodopent-3-enoic acid methyl ester
• 英文别名: methyl (E,2E)-2-ethylidene-4-iodopent-3-enoate
• CAS: 853335-59-8
• 化学式: C₈H₁₁IO₂
• 分子量: 266.079
• InChiKey: FMOKOKJMFXXLLC-HVUXDCMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,3E)-2-ethylidene-4-iodopent-3-enoic acid methyl ester 在 palladium diacetate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三苯胂 、 sodium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-ethylidene-4,10-dimethyl-11-oxo-11-(2-oxo-5-(triethylsilanyloxy)-5-(2-(triethylsilanyloxy)ethyl)-1-(2-(trimethylsilanyl)ethoxymethyl)-2,5-dihydro-1H-pyrrol-3-yl)-undeca-3,5,7,9-tetraenoic acid methyl ester
  参考文献：
  名称：

  Total Synthesis of Lucilactaene, A Cell Cycle Inhibitor Active in p53-Inactive Cells

  摘要：

  Hetero-bis-metalated 1,3-butadiene is employed in the lynchpin coupling of synthetic fragments of the side chain of the antitumor agent, lucilactaene. Sequential Stille and Suzuki-Miyaura couplings interpolate this unique boron/tin diene into the pentaene chain. The total synthesis of lucilactaene was accomplished efficiently, in just eight linear steps.

  DOI：

  10.1021/ja056217g
• 作为产物：
  描述：

  (2E,3E)-2-ethylidene-4-(phenyldimethylsilyl)pent-3-enoic acid methyl ester 在 2,6-二甲基吡啶 、 N-碘代丁二酰亚胺 作用下， 以 various solvent(s) 为溶剂， 反应 0.03h， 以89%的产率得到(2E,3E)-2-ethylidene-4-iodopent-3-enoic acid methyl ester
  参考文献：
  名称：

  Total Synthesis of Lucilactaene, A Cell Cycle Inhibitor Active in p53-Inactive Cells

  摘要：

  Hetero-bis-metalated 1,3-butadiene is employed in the lynchpin coupling of synthetic fragments of the side chain of the antitumor agent, lucilactaene. Sequential Stille and Suzuki-Miyaura couplings interpolate this unique boron/tin diene into the pentaene chain. The total synthesis of lucilactaene was accomplished efficiently, in just eight linear steps.

  DOI：

  10.1021/ja056217g

文献信息

• Tandem Stille/Suzuki−Miyaura Coupling of a Hetero-Bis-metalated Diene. Rapid, One-Pot Assembly of Polyene Systems
  作者：Robert S. Coleman、Matthew C. Walczak

  DOI：10.1021/ol050768u

  日期：2005.5.1

  The synthesis of a hetero-bis-metallo 1,3-butadiene is reported, and its use as an orthogonal Stille and Suzuki-Miyaura coupling partner is detailed. The tin/boron diene participated successfully in a one-pot, sequential Stille and Suzuki-Miyaura coupling protocol, and its utility was demonstrated in the two-step construction of the pentaene side chain of the Fusarium metabolite lucilactaene.