Aziridine, 1-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]- | 192657-68-4

• 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: Aziridine, 1-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-
• 英文别名: 2-(aziridin-1-yl)ethoxy-tert-butyl-dimethylsilane
• CAS: 192657-68-4
• 化学式: C₁₀H₂₃NOSi
• 分子量: 201.384
• InChiKey: NSLYKTYIRDLCHS-UHFFFAOYSA-N

物化性质

• 沸点：
  208.6±23.0 °C(Predicted)
• 密度：
  0.902±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Aziridine, 1-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]- 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以2.85 g的产率得到1-(2-(tert-butyldimethylsiloxy)ethyl)aziridine borane
  参考文献：
  名称：

  The stereochemistry of aziridine borane lithiation: diastereoselectivity and enantioselectivity

  摘要：

  Lithiation of 1-methylaziridine borane, 1-(tert-butyldimethylsiloxyethyl)aziridine borane, or 1-(tert-butyldimethylsiloxyethyl)-2-methylaziridine borane occurs syn to the boron substituent, while lithiation of 1-(tert-butyldimethylsiloxyethyl)-2-trimethylstannylaziridine borane occurs anti to boron as well as silicon due to the steric effect of trimethylsilyl group (s-butyllithium was used in all cases). Kinetically controlled lithiation in the first three cases results from a combination of steric and electrostatic effects. Enantioselective lithiation occurs in the presence of (-)-sparteine, with product enantioselectivities near 70% ee. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.035
• 作为产物：
  描述：

  1-羟乙基氮丙啶 、 叔丁基二甲基氯硅烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以56%的产率得到Aziridine, 1-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-
  参考文献：
  名称：

  氮丙啶（II）催化的氮丙啶与异氰酸酯的[3 + 2]交叉偶联反应。

  摘要：

  [反应：请参见文字]。在镍催化剂的存在下，氮丙啶与异氰酸酯的环加成反应顺利进行，并且以高收率分离出五种亚氨基恶唑烷衍生物。当在NiI2存在下进行反应时，可获得最佳结果，更长的反应时间使亚氨基恶唑烷异构化为相应的咪唑烷酮衍生物。

  DOI：

  10.1021/ol052417l

文献信息

• Cycloaddition of tertiary aziridines and carbon dioxide using a recyclable organocatalyst, 1,3-di-tert-butylimidazolium-2-carboxylate: straightforward access to 3-substituted 2-oxazolidones
  作者：Atsushi Ueno、Yoshihito Kayaki、Takao Ikariya

  DOI：10.1039/c2gc36414j

  日期：——

  Imidazolium-2-carboxylates derived from N-heterocyclic carbenes (NHCs) and CO2 serve as efficient catalysts for CO2-carboxylation of tertiary aziridines bearing various substituents such as halogens, ether, olefin, ester, acetal, and nitro groups on the aziridine ring in 2-propanol, leading to 3-substituted-2-oxazolidones in good to excellent yields and with high selectivity. The NHC–CO2 adducts facilitate

  咪唑-2-羧酸盐衍生自 N-杂环卡宾（NHCs）和CO 2起到了有效的作用催化剂的CO 2-羧化氮丙啶 带有各种取代基，例如 卤素， 醚， 烯烃， 酯， 乙缩醛，以及氮丙啶环上的硝基 2-丙醇，从而以高至优异的收率和高选择性产生3-取代的-2-恶唑烷酮。NHC-CO 2加合物促进了CO 2部分对核素的亲核攻击。氮丙啶，其中取代基在羧化过程中是完整的。这催化剂 成功回收了五次，没有明显的活性损失。
• Aziridine Lithiation Using Lewis Acid Activation
  作者：Edwin Vedejs、John T. Kendall

  DOI：10.1021/ja970164o

  日期：1997.7.1
• [3+2] Cross-Coupling Reactions of Aziridines with Isocyanates Catalyzed by Nickel(II) Iodide
  作者：Takeshi Munegumi、Isao Azumaya、Takako Kato、Hyuma Masu、Shinichi Saito

  DOI：10.1021/ol052417l

  日期：2006.2.1

  [reaction: see text]. Cycloaddition of aziridines with isocyanates proceeded smoothly in the presence of a nickel catalyst, and five iminooxazolidine derivatives were isolated in good yields. The best result was obtained when the reaction was carried out in the presence of NiI2, and a longer reaction time allowed the isomerization of the iminooxazolidine to the corresponding imidazolidinone derivatives

  [反应：请参见文字]。在镍催化剂的存在下，氮丙啶与异氰酸酯的环加成反应顺利进行，并且以高收率分离出五种亚氨基恶唑烷衍生物。当在NiI2存在下进行反应时，可获得最佳结果，更长的反应时间使亚氨基恶唑烷异构化为相应的咪唑烷酮衍生物。
• The stereochemistry of aziridine borane lithiation: diastereoselectivity and enantioselectivity
  作者：E Vedejs、A.S Bhanu Prasad、J.T Kendall、J.S Russel

  DOI：10.1016/j.tet.2003.09.035

  日期：2003.12

  Lithiation of 1-methylaziridine borane, 1-(tert-butyldimethylsiloxyethyl)aziridine borane, or 1-(tert-butyldimethylsiloxyethyl)-2-methylaziridine borane occurs syn to the boron substituent, while lithiation of 1-(tert-butyldimethylsiloxyethyl)-2-trimethylstannylaziridine borane occurs anti to boron as well as silicon due to the steric effect of trimethylsilyl group (s-butyllithium was used in all cases). Kinetically controlled lithiation in the first three cases results from a combination of steric and electrostatic effects. Enantioselective lithiation occurs in the presence of (-)-sparteine, with product enantioselectivities near 70% ee. (C) 2003 Elsevier Ltd. All rights reserved.