methyl (2E,3E,5E,7E)-2-ethylidene-4-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octa-3,5,7-trienoate | 853335-61-2

• 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 (2E,3E,5E,7E)-2-ethylidene-4-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octa-3,5,7-trienoate
• 英文别名: (2E,3E,5E,7E)-2-ethylidene-4-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octa-3,5,7-trienoate methyl ester
• CAS: 853335-61-2
• 化学式: C₁₈H₂₇BO₄
• 分子量: 318.221
• InChiKey: GZOJSQIKTORYBR-XBVHIABBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2E,3E,5E,7E)-2-ethylidene-4-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octa-3,5,7-trienoate 在 palladium diacetate 、 sodium carbonate 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 lucilactaene
  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 、 tris-(dibenzylideneacetone)dipalladium(0) 、 N-碘代丁二酰亚胺 、 三苯胂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.03h， 生成 methyl (2E,3E,5E,7E)-2-ethylidene-4-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octa-3,5,7-trienoate
  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.