ethyl (E,E,E)-2-methyl-9-bromo-2,4,8-nonatrien-6-ynoate | 548757-31-9

• 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: ethyl (E,E,E)-2-methyl-9-bromo-2,4,8-nonatrien-6-ynoate
• 英文别名: (2E,4E,8E)-2-methyl-9-bromo-2,4,8-nonatrien-6-ynoate；ethyl (2E,4E,8E)-9-bromo-2-methylnona-2,4,8-trien-6-ynoate
• CAS: 548757-31-9
• 化学式: C₁₂H₁₃BrO₂
• 分子量: 269.138
• InChiKey: LPGOLJWGRJVICV-HJHGIKLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (4R,5R,6E,8S)-4,6,8-trimethyl-5-(t-butyldimethylsilyloxy)-10-phenyl-6-decen-2-yne 、 ethyl (E,E,E)-2-methyl-9-bromo-2,4,8-nonatrien-6-ynoate 在 Schwartz's reagent 、 zinc(II) chloride 、 bis-triphenylphosphine-palladium(II) chloride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 22.67h， 以57%的产率得到ethyl (2E,4E,8E,10E,12R,13R,14E,16S)-2,10,12,14,16-pentamethyl-13-(t-butyldimethylsilyloxy)-18-phenyl-2,4,8,10,14-octadecapentaen-6-ynoate
  参考文献：
  名称：

  Efficient and Selective Synthesis of 6,7-Dehydrostipiamide via Zr-Catalyzed Asymmetric Carboalumination and Pd-Catalyzed Cross-Coupling of Organozincs

  摘要：

  6,7-Dehydrostipiamide has been synthesized in 23% yield in 15 steps in the longest linear sequence through the application of the Zr-catalyzed asymmetric carboalumination and the Pd-catalyzed organozinc cross-coupling in addition to the Brown crotylboration, the Corey-Peterson olefination, and the Corey-Fuchs reaction for carbon-carbon bond formation.

  DOI：

  10.1021/ol048905v
• 作为产物：
  描述：

  (2E,4E)-ethyl 2-methyl-7-(trimethylsilyl)hepta-2,4-dien-6-ynoate 在 四丁基氟化铵 、 zinc dibromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 生成 ethyl (E,E,E)-2-methyl-9-bromo-2,4,8-nonatrien-6-ynoate
  参考文献：
  名称：

  Highly Satisfactory Alkynylation of Alkenyl Halides via Pd-Catalyzed Cross-Coupling with Alkynylzincs and Its Critical Comparison with the Sonogashira Alkynylation

  摘要：

  [GRAPHICS]The Pd-catalyzed alkynylation of various alkenyl halides and triflates with alkynylzincs proceeds well even with alkynyl derivatives containing electron-withdrawing groups. The reaction appears to be highly general. Noteworthy is that the corresponding Sonogashira reactions under various reported conditions are significantly less satisfactory in all cases performed in this study.

  DOI：

  10.1021/ol030010f

文献信息

• Highly Satisfactory Alkynylation of Alkenyl Halides via Pd-Catalyzed Cross-Coupling with Alkynylzincs and Its Critical Comparison with the Sonogashira Alkynylation
  作者：Ei-ichi Negishi、Mingxing Qian、Fanxing Zeng、Luigi Anastasia、David Babinski

  DOI：10.1021/ol030010f

  日期：2003.5.1

  [GRAPHICS]The Pd-catalyzed alkynylation of various alkenyl halides and triflates with alkynylzincs proceeds well even with alkynyl derivatives containing electron-withdrawing groups. The reaction appears to be highly general. Noteworthy is that the corresponding Sonogashira reactions under various reported conditions are significantly less satisfactory in all cases performed in this study.
• Efficient and Selective Synthesis of 6,7-Dehydrostipiamide via Zr-Catalyzed Asymmetric Carboalumination and Pd-Catalyzed Cross-Coupling of Organozincs
  作者：Xingzhong Zeng、Fanxing Zeng、Ei-ichi Negishi

  DOI：10.1021/ol048905v

  日期：2004.9.1

  6,7-Dehydrostipiamide has been synthesized in 23% yield in 15 steps in the longest linear sequence through the application of the Zr-catalyzed asymmetric carboalumination and the Pd-catalyzed organozinc cross-coupling in addition to the Brown crotylboration, the Corey-Peterson olefination, and the Corey-Fuchs reaction for carbon-carbon bond formation.