benzyl(hepta-1,6-diynyl)dimethylsilane | 1415667-40-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl(hepta-1,6-diynyl)dimethylsilane
• CAS: 1415667-40-1
• 化学式: C₁₆H₂₀Si
• 分子量: 240.42
• InChiKey: OGRDKDSHAYNJKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  benzyl(hepta-1,6-diynyl)dimethylsilane 在 正丁基锂 、 carbon monoxide,cobalt,cyclopenta-1,3-diene 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 氯苯 为溶剂， 反应 6.5h， 生成 4-(benzyldimethylsilyl)-1,2,3,6,7,8,9,10-octahydrocyclohepta[e]inden-10-ol
  参考文献：
  名称：

  Metal-Catalyzed Syntheses of Abridged CDE Rings of Rubriflordilactones A and B

  摘要：

  The development of complementary palladium- and cobalt-catalyzed approaches to tricyclic arylsilanes suitable for elaboration into the CDE ring systems of rubriflordilactones A and B is reported. Microwave conditions are required to effect a cobalt-catalyzed triyne cyclotrimerization, which critically depends on the substitution pattern of the triyne termini. Mild conditions to elaborate these arylsilanes to the CDE cores of the natural products are described.

  DOI：

  10.1021/ol303041j
• 作为产物：
  描述：

  1,6-庚二炔 、 苄基二甲基氯硅烷 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 3.75h， 以25%的产率得到benzyl(hepta-1,6-diynyl)dimethylsilane
  参考文献：
  名称：

  Metal-Catalyzed Syntheses of Abridged CDE Rings of Rubriflordilactones A and B

  摘要：

  The development of complementary palladium- and cobalt-catalyzed approaches to tricyclic arylsilanes suitable for elaboration into the CDE ring systems of rubriflordilactones A and B is reported. Microwave conditions are required to effect a cobalt-catalyzed triyne cyclotrimerization, which critically depends on the substitution pattern of the triyne termini. Mild conditions to elaborate these arylsilanes to the CDE cores of the natural products are described.

  DOI：

  10.1021/ol303041j

文献信息

• Palladium-catalyzed cyclization of bromoenynamides to tricyclic azacycles: synthesis of trikentrin-like frameworks
  作者：Craig D. Campbell、Rebecca L. Greenaway、Oliver T. Holton、Helen A. Chapman、Edward A. Anderson

  DOI：10.1039/c3cc45634j

  日期：——

  Palladium-catalyzed cascade cyclization of bromoenynamides equipped with an additional alkyne or ynamide substituent affords azatricyclic products. Using 5- to 7-membered ring tethers, this chemistry offers a regiospecific route to highly-functionalized azacycles. Elaboration to the trikentrin B skeleton is achieved from the arylsilane cyclization products.

  酸化铂催化的溴烯炔酰胺级联环化反应，配备额外的炔烃或炔腈取代基，能够获得氮杂三环产物。利用5到7元环的连接体，这种化学反应提供了一条区域选择性的路径，合成高度功能化的氮杂环。通过芳基硅烷环化产物，可以进一步合成三嵌环B骨架。