(2S,3S)-3-(tert-butyldimethylsilanyloxymethyl)aziridine-2-carboxylic acid ethyl ester | 198829-62-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S)-3-(tert-butyldimethylsilanyloxymethyl)aziridine-2-carboxylic acid ethyl ester
• 英文别名: 3-(tert-butyldimethylsilanyloxymethyl)-aziridine-2-carboxylic acid ethyl ester；(2S,3S)-ethyl 3-((tert-butyldimethylsilyloxy)methyl)aziridine-2-carboxylate；ethyl (2S,3S)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]aziridine-2-carboxylate
• CAS: 198829-62-8
• 化学式: C₁₂H₂₅NO₃Si
• 分子量: 259.421
• InChiKey: DAEHKIUTEOCDAP-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  57.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-(tert-butyldimethylsilanyloxymethyl)aziridine-2-carboxylic acid ethyl ester 在 二异丁基氢化铝 作用下， 生成 6-(tert-butyldimethylsilanyloxymethyl)-2-[3-(tert-butyldimethylsilanyloxymethyl)-aziridin-2-yl]-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol
  参考文献：
  名称：

  Amphoteric Amino Aldehydes Reroute the Aza-Michael Reaction

  摘要：

  Amphoteric amino aldehydes, which exist as stable dimers, participate in an aza-Michael/aldol domino reaction with alpha,beta-unsaturated aldehydes to afford stable 1,5-aminohydroxyaldehydes in high yields and diastereoselectivies. The reaction outcome hinges upon the dimeric nature of amphoteric amino aldehydes and the orthogonality between the NH aziridine and the two aldehyde functionalities during the reaction. Through the use of reaction conditions that disfavor dimer dissociation, the aza-Michael process has been directed toward a novel 8-(enolendo)-exo-trig cyclization. The results described herein further demonstrate the potential of amphoteric molecules in reaction discovery.

  DOI：

  10.1021/ja9072194
• 作为产物：
  描述：

  L-(+)-酒石酸二乙酯 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 27.75h， 生成 (2S,3S)-3-(tert-butyldimethylsilanyloxymethyl)aziridine-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Readily Available Unprotected Amino Aldehydes

  摘要：

  We report a new class of bench-stable compounds that contain seemingly incompatible functional groups: an aldehyde and an unprotected secondary amine. The thermodynamic driving force to undergo condensation between these two functionalities is offset by a high barrier imposed on this process by the aziridine ring strain. The resulting amino aldehydes exist as dimers and in the solid state. They are stable to epimerization and contain two orthogonal reaction centers, namely, an amine/aziridine and an aldehyde. Their ability to act as linchpins has been evaluated in complex heterocycle synthesis. For instance, pentacyclic frameworks can be made in one simple operation using N-benzyltryptamine as the reaction partner. Construction of other molecular skeletons with minimal use of protecting group manipulations should be feasible.

  DOI：

  10.1021/ja065898s

文献信息

• WO2008/46232
  申请人：——

  公开号：——

  公开（公告）日：——
• Amphoteric Amino Aldehydes Reroute the Aza-Michael Reaction
  作者：Ryan Hili、Andrei K. Yudin

  DOI：10.1021/ja9072194

  日期：2009.11.18

  Amphoteric amino aldehydes, which exist as stable dimers, participate in an aza-Michael/aldol domino reaction with alpha,beta-unsaturated aldehydes to afford stable 1,5-aminohydroxyaldehydes in high yields and diastereoselectivies. The reaction outcome hinges upon the dimeric nature of amphoteric amino aldehydes and the orthogonality between the NH aziridine and the two aldehyde functionalities during the reaction. Through the use of reaction conditions that disfavor dimer dissociation, the aza-Michael process has been directed toward a novel 8-(enolendo)-exo-trig cyclization. The results described herein further demonstrate the potential of amphoteric molecules in reaction discovery.
• Amphoteric Amino Aldehydes Enable Rapid Assembly of Unprotected Amino Alcohols
  作者：Ryan Hili、Andrei K. Yudin

  DOI：10.1002/anie.200705776

  日期：2008.5.19
• Readily Available Unprotected Amino Aldehydes
  作者：Ryan Hili、Andrei K. Yudin

  DOI：10.1021/ja065898s

  日期：2006.11.1

  We report a new class of bench-stable compounds that contain seemingly incompatible functional groups: an aldehyde and an unprotected secondary amine. The thermodynamic driving force to undergo condensation between these two functionalities is offset by a high barrier imposed on this process by the aziridine ring strain. The resulting amino aldehydes exist as dimers and in the solid state. They are stable to epimerization and contain two orthogonal reaction centers, namely, an amine/aziridine and an aldehyde. Their ability to act as linchpins has been evaluated in complex heterocycle synthesis. For instance, pentacyclic frameworks can be made in one simple operation using N-benzyltryptamine as the reaction partner. Construction of other molecular skeletons with minimal use of protecting group manipulations should be feasible.
• Hili, Ryan; Rai, Vishal; Yudin, Andrei K., Journal of the American Chemical Society, 2010, vol. 132, p. 2889 - 2891
  作者：Hili, Ryan、Rai, Vishal、Yudin, Andrei K.

  DOI：——

  日期：——