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 | 871579-59-8

• 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: 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
• 英文别名: methyl (2E,3E,5E,7E,9E)-2-ethylidene-4,10-dimethyl-11-oxo-11-[2-oxo-5-triethylsilyloxy-5-(2-triethylsilyloxyethyl)-1-(2-trimethylsilylethoxymethyl)pyrrol-3-yl]undeca-3,5,7,9-tetraenoate
• CAS: 871579-59-8
• 化学式: C₄₀H₆₉NO₇Si₃
• 分子量: 760.247
• InChiKey: RHCOZJHADAANPC-KOBOCBNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.89
• 重原子数：
  51
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  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 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以64%的产率得到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 、 palladium diacetate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 N-碘代丁二酰亚胺 、 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 24.03h， 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

文献信息

• Total Synthesis of Lucilactaene, A Cell Cycle Inhibitor Active in p53-Inactive Cells
  作者：Robert S. Coleman、Matthew C. Walczak、Erica L. Campbell

  DOI：10.1021/ja056217g

  日期：2005.11.23

  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.