(10R)-B-(3-methylbut-3-en-1-ynyl)-10-trimethylsilyl-9-borabicyclo[3.3.2]decane | 906650-64-4

• 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: (10R)-B-(3-methylbut-3-en-1-ynyl)-10-trimethylsilyl-9-borabicyclo[3.3.2]decane
• 英文别名: B-(3-methylbut-3-en-1-ynyl)-(10R)-trimethylsilyl-9-borabicyclo[3.3.2]decane；(R)-CH2C(CH3)CCB(C8H14)CH(trimethylsilyl)；(R)-CH2C(CH3)CCB(C8H14)CH(TMS)；trimethyl-[(10R)-9-(3-methylbut-3-en-1-ynyl)-9-borabicyclo[3.3.2]decan-10-yl]silane
• CAS: 906650-64-4
• 化学式: C₁₇H₂₉BSi
• 分子量: 272.314
• InChiKey: GJIXOPDVXRKKRN-JCYILVPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (10R)-B-(3-methylbut-3-en-1-ynyl)-10-trimethylsilyl-9-borabicyclo[3.3.2]decane 、 三甲基硅烷化重氮甲烷 以 正己烷 为溶剂， 以100%的产率得到(R)-(trimethylsilyl)CHCC(C(CH3)CH2)B(C8H14)CH(trimethylsilyl)
  参考文献：
  名称：

  通过1,2-插入-1,3-硼酸重排，由炔基硼烷不对称地合成异构纯的烯丙基硼烷。

  摘要：

  DOI：

  10.1002/anie.200603467
• 作为产物：
  描述：

  B-甲氧基-10-三甲基甲硅烷基-9-硼二环(3.3.2)癸烷 以 乙醚 、 乙腈 为溶剂， 反应 8.0h， 生成 (10R)-B-(3-methylbut-3-en-1-ynyl)-10-trimethylsilyl-9-borabicyclo[3.3.2]decane
  参考文献：
  名称：

  N-Propargylamides via the Asymmetric Michael Addition of B-Alkynyl-10-TMS-9- borabicyclo[3.3.2]decanes to N-Acylimines

  摘要：

  The asymmetric synthesis of N-propargylamides through Michael addition of the alkynylborane 1 to N-acylimines is reported. The N-acetylimines provide the best substrates for the process exhibiting high selectivity (56-95% ee) with predictable stereochemistry. In several cases, 5 crystallizes in essentially pure form (97-99% ee) and a single-crystal X-ray structure was also obtained for 5g (R-1 = R-2 = Me, R-3 = o-Cl-C6C4). The process regenerates 4 for its direct conversion back to 1 and facilitates the efficient recovery of the pseudoephedrine.

  DOI：

  10.1021/ol0611595

文献信息

• Asymmetric Synthesis of Isomerically Pure Allenyl Boranes from Alkynyl Boranes through a 1,2-Insertion–1,3-Borotropic Rearrangement
  作者：Eda Canales、Ana Z. Gonzalez、John A. Soderquist

  DOI：10.1002/anie.200603467

  日期：2007.1.8
• <i>N</i>-Propargylamides via the Asymmetric Michael Addition of <i>B</i>-Alkynyl-10-TMS-9- borabicyclo[3.3.2]decanes to <i>N</i>-Acylimines
  作者：Ana Z. Gonzalez、Eda Canales、John A. Soderquist

  DOI：10.1021/ol0611595

  日期：2006.7.1

  The asymmetric synthesis of N-propargylamides through Michael addition of the alkynylborane 1 to N-acylimines is reported. The N-acetylimines provide the best substrates for the process exhibiting high selectivity (56-95% ee) with predictable stereochemistry. In several cases, 5 crystallizes in essentially pure form (97-99% ee) and a single-crystal X-ray structure was also obtained for 5g (R-1 = R-2 = Me, R-3 = o-Cl-C6C4). The process regenerates 4 for its direct conversion back to 1 and facilitates the efficient recovery of the pseudoephedrine.