3-(2,8-Dioxa-5-azonia-1-boranuidabicyclo[3.3.0]octan-1-yl)prop-1-ynyl-dimethyl-phenylsilane | 1196787-48-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-(2,8-Dioxa-5-azonia-1-boranuidabicyclo[3.3.0]octan-1-yl)prop-1-ynyl-dimethyl-phenylsilane
• CAS: 1196787-48-0
• 化学式: C₁₅H₂₂BNO₂Si
• 分子量: 287.242
• InChiKey: NBZLXLRKFYVXIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.03
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  22.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2,8-Dioxa-5-azonia-1-boranuidabicyclo[3.3.0]octan-1-yl)prop-1-ynyl-dimethyl-phenylsilane 、 4-甲氧基苯甲醛 在 diethylzinc 、 盐酸 作用下， 以 二氯甲烷 、 甲苯 、 醋酸异丙酯 、 水 为溶剂， 反应 1.17h， 以90%的产率得到4-[Dimethyl(phenyl)silyl]-1-(4-methoxyphenyl)but-3-yn-1-ol
  参考文献：
  名称：

  Zinc Catalyzed and Mediated Propargylations with Propargyl Boronates

  摘要：

  The utility of allenyl and propargyl boronates for the propargylation of aldehydes and ketones mediated by zinc is presented. The reaction Is catalytic in zinc with allenyl or propargyl borolanes. The propargylation with crystalline and air-stable propargyl diethanolamine boronates was also achieved. A catalytic cycle is proposed, and preliminary mechanistic studies are discussed.

  DOI：

  10.1021/ol902457m
• 作为产物：
  描述：

  、 二乙醇胺 以 甲基叔丁基醚 为溶剂， 反应 1.5h， 以2.86 g的产率得到3-(2,8-Dioxa-5-azonia-1-boranuidabicyclo[3.3.0]octan-1-yl)prop-1-ynyl-dimethyl-phenylsilane
  参考文献：
  名称：

  Zinc Catalyzed and Mediated Propargylations with Propargyl Boronates

  摘要：

  The utility of allenyl and propargyl boronates for the propargylation of aldehydes and ketones mediated by zinc is presented. The reaction Is catalytic in zinc with allenyl or propargyl borolanes. The propargylation with crystalline and air-stable propargyl diethanolamine boronates was also achieved. A catalytic cycle is proposed, and preliminary mechanistic studies are discussed.

  DOI：

  10.1021/ol902457m

文献信息

• Zinc Catalyzed and Mediated Propargylations with Propargyl Boronates
  作者：Daniel R. Fandrick、Keith R. Fandrick、Jonathan T. Reeves、Zhulin Tan、Courtney S. Johnson、Heewon Lee、Jinhua J. Song、Nathan K. Yee、Chris H. Senanayake

  DOI：10.1021/ol902457m

  日期：2010.1.1

  The utility of allenyl and propargyl boronates for the propargylation of aldehydes and ketones mediated by zinc is presented. The reaction Is catalytic in zinc with allenyl or propargyl borolanes. The propargylation with crystalline and air-stable propargyl diethanolamine boronates was also achieved. A catalytic cycle is proposed, and preliminary mechanistic studies are discussed.