(2S,3R)-tert-butyl 3-isobutylaziridine-2-carboxylate | 1195982-82-1

• 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,3R)-tert-butyl 3-isobutylaziridine-2-carboxylate
• 英文别名: tert-butyl (2S,3R)-3-isobutylaziridine-2-carboxylate；tert-butyl (2S,3R)-3-(2-methylpropyl)aziridine-2-carboxylate
• CAS: 1195982-82-1
• 化学式: C₁₁H₂₁NO₂
• 分子量: 199.293
• InChiKey: PFIFBRMNKFZMGT-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  48.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-tert-butyl 3-isobutylaziridine-2-carboxylate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 (2R,4R,5S,6R)-6-isobutyl-2-((2S,3R)-3-isobutylaziridin-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：

  (R)-N-Boc-2-isobutylaziridine 在 2,2,6,6-tetramethylpiperidinyl-lithium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以70%的产率得到(2S,3R)-tert-butyl 3-isobutylaziridine-2-carboxylate
  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

文献信息

• 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：——
• [EN] METHODS OF PREPARING CYCLIC AMINO ACID MOLECULES USING ARYLBORONIC OR ARYLBORINIC ACID CATALYSTS<br/>[FR] PROCÉDÉS DE SYNTHÈSE DE MOLÉCULES D'ACIDES AMINÉS CYCLIQUES UTILISANT DES CATALYSEURS DE TYPE ACIDE ARYLBORONIQUE OU ARYLBORINIQUE
  申请人：UNIV TORONTO

  公开号：WO2012109735A1

  公开（公告）日：2012-08-23

  Macrocyclization of amino acids or linear peptides upon reaction with amphoteric amino aldehydes and isocyanides in the presence of a catalyst selected from an arylboronic acid or an aryl borinic acid is provided.