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 | 770711-50-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 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
• 英文别名: ethyl (2E,4E,8E,10E,12R,13R,14E,16S)-13-[tert-butyl(dimethyl)silyl]oxy-2,10,12,14,16-pentamethyl-18-phenyloctadeca-2,4,8,10,14-pentaen-6-ynoate
• CAS: 770711-50-7
• 化学式: C₃₇H₅₄O₃Si
• 分子量: 574.919
• InChiKey: LHGUSZYWBSIFJS-OLYWGTENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  41
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  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 在 lithium hydroxide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 30.0h， 生成 (2E,4E,8E,10E,14E)-(12R,13R,16S)-13-Hydroxy-2,10,12,14,16-pentamethyl-18-phenyl-octadeca-2,4,8,10,14-pentaen-6-ynoic acid
  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：

  (3E,5R,6R,7E,9S)-1-trimethylsilyl-3,5,7,9-tetramethyl-6-(t-butyldimethylsilyloxy)-11-phenyl-3,7-undecadien-1-yne 在 Schwartz's reagent 、 正丁基锂 、 potassium carbonate 、 二异丙胺 、 zinc dibromide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 12.58h， 生成 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

文献信息

• 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.