azidodimethylisopropylsilane | 110674-23-2

• 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: azidodimethylisopropylsilane
• 英文别名: Azido(dimethyl)(propan-2-yl)silane；azido-dimethyl-propan-2-ylsilane
• CAS: 110674-23-2
• 化学式: C₅H₁₃N₃Si
• 分子量: 143.264
• InChiKey: KAVMYSIPAJXDOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氧化环己烯 、 azidodimethylisopropylsilane 以 1,2-二氯丁烷 为溶剂， 以85%的产率得到(1S,2S)-1-azido-2-(isopropyldimethylsiloxy)cyclohexane
  参考文献：
  名称：

  Enantioselective lewis acid catalysts of the early transition metals

  摘要：

  早期过渡金属的可选择活性Lewis酸催化剂已经制备好，这些催化剂在不对称加成催化中很有用。催化剂配合物包括IV族或V族金属的烷氧基和光学活性的三烷基醇胺或二烷醇胺配体。

  公开号：

  US05231203A1
• 作为产物：
  描述：

  二甲基异丙基氯硅烷 、 叠氮化钠 以72%的产率得到
  参考文献：
  名称：

  YAMASHITA, HIROYUKI, BULL. CHEM. SOC. JAP., 61,(1988) N 4, C. 1213-1220

  摘要：

  DOI：

文献信息

• Paterson, Ian; Berrisford, David J., Angewandte Chemie, 1992, vol. 104, # 9, p. 1204 - 1205
  作者：Paterson, Ian、Berrisford, David J.

  DOI：——

  日期：——
• YAMASHITA HIROYUKI, CHEM. LETT.,(1987) N 3, 525-528
  作者：YAMASHITA HIROYUKI

  DOI：——

  日期：——
• Chiral Lewis acid catalysis. Enantioselective addition of azide to meso epoxides
  作者：William A. Nugent

  DOI：10.1021/ja00033a090

  日期：1992.3
• Mechanistic Studies of the Zirconium−Triisopropanolamine-Catalyzed Enantioselective Addition of Azide to Cyclohexene Oxide
  作者：Brent W. McCleland、William A. Nugent、M. G. Finn

  DOI：10.1021/jo9809377

  日期：1998.9.1

  The mechanism of the enantioselective ring-opening of cyclohexene oxide by Me3SiN3, catalyzed by zirconium complexes of the C-3-symmetric ligand (+)-(S,S,S)-triisopropanolamine, has been investigated. Measurements of molecular weights of precatalyst species show that complexes are formed with average trimeric aggregation. Kinetics measurements reveal the overall process to be approximately half order in total zirconium, epoxide, and Me3SiN3 components. The reaction also shows a strong nonlinear relationship between enantiomeric excess of product azido ether vs the incorporation of (R,S,S)-triisopropanolamine ligand in the catalyst mixture. On the basis of these and other results, a preequilibrium interconversion of dimeric and tetrameric zirconium-triisopropanolamine species is proposed to occur rapidly with respect to the rate of epoxide ring-opening, with the dimeric form being the active catalyst. The reaction is accelerated by silyl ethers or by small amounts of water or alcohol, whereas larger amounts of protic additives inhibit the reaction. Enantioselectivity is eroded at catalyst concentrations less than 1 mole-percent and at high concentrations of cyclohexene oxide. Both enantioselectivity and rate are influenced to a small extent by the nature of the silyl azide employed for the first catalytic turnover, suggesting that a silyl fragment becomes irreversibly incorporated in the catalyst structure. It is proposed that catalytic activity requires the cooperative action of two zirconium centers for the binding and delivery of azide to epoxide.
• Enantioselective lewis acid catalysts of the early transition metals
  申请人：E. I. du Pont de Nemours and Company

  公开号：US05231203A1

  公开（公告）日：1993-07-27

  Optionally active Lewis acid catalysts of the early transition metals which are useful in the catalysis of asymmetric additions have been prepared. The catalyst complexes comprise an alkoxide of a group IV or group V metal and an optically active trialkanolamine or dialkanolamine ligand.

  早期过渡金属的可选择活性Lewis酸催化剂已经制备好，这些催化剂在不对称加成催化中很有用。催化剂配合物包括IV族或V族金属的烷氧基和光学活性的三烷基醇胺或二烷醇胺配体。