N-tert-butoxycarbonyl-1-propylbut-3-enamine | 1335042-33-5

• 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: N-tert-butoxycarbonyl-1-propylbut-3-enamine
• 英文别名: Tert-butyl hept-1-en-4-ylcarbamate；tert-butyl N-hept-1-en-4-ylcarbamate
• CAS: 1335042-33-5
• 化学式: C₁₂H₂₃NO₂
• 分子量: 213.32
• InChiKey: IVUJCEAEFHYMLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-1-propylbut-3-enamine 、 对甲基苯磺酰异氰酸酯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Pd(II)-Catalyzed Allylic C–H Amination for the Preparation of 1,2- and 1,3-Cyclic Ureas

  摘要：

  A general synthesis of 1,2- and 1,3-cyclic ureas is accomplished by intramolecular allylic C-H amination employing Pd(TFA)(2)/bis-sulfoxide as a catalyst. By careful modification of substrates and catalyst, a variety of 1,2-cyclic ureas are accessible from not previously employed terminal olefins substituted in allylic or vinylic positions. Furthermore, MS4A is found to be an effective additive for the synthesis of 1,3-cyclic ureas in good yields and excellent diastereoselectivities.

  DOI：

  10.1021/ol5037453
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 1-Propyl-but-3-enylamine 以 四氢呋喃 为溶剂， 生成 N-tert-butoxycarbonyl-1-propylbut-3-enamine
  参考文献：
  名称：

  Pd(II)-Catalyzed Allylic C–H Amination for the Preparation of 1,2- and 1,3-Cyclic Ureas

  摘要：

  A general synthesis of 1,2- and 1,3-cyclic ureas is accomplished by intramolecular allylic C-H amination employing Pd(TFA)(2)/bis-sulfoxide as a catalyst. By careful modification of substrates and catalyst, a variety of 1,2-cyclic ureas are accessible from not previously employed terminal olefins substituted in allylic or vinylic positions. Furthermore, MS4A is found to be an effective additive for the synthesis of 1,3-cyclic ureas in good yields and excellent diastereoselectivities.

  DOI：

  10.1021/ol5037453

文献信息

• Indium-Mediated Asymmetric Barbier-Type Allylation of Aldimines in Alcoholic Solvents:  Synthesis of Optically Active Homoallylic Amines
  作者：Tirayut Vilaivan、Chutima Winotapan、Vorawit Banphavichit、Tetsuro Shinada、Yasufumi Ohfune

  DOI：10.1021/jo0477244

  日期：2005.4.1

  Chiral aldimines derived from phenylglycinol were diastereoselectively allylated with indium powder/allyl bromide in alcoholic solvents. Both aliphatic and aromatic aldimines provided good yield of the desired products with high diastereoselectivity. A racemization-free protocol for removal of the phenylglycinol auxiliary was also developed. The stereochemical assignment of the homoallylic amine was

  将衍生自苯甘醇的手性醛亚胺在酒精溶剂中与铟粉/溴代烯丙基酯非对映选择性地烯丙基化。脂族和芳族醛亚胺都提供了具有高非对映选择性的所需产物的良好产率。还开发了用于消去苯基甘醇辅助剂的无消旋方案。通过NMR光谱对均烯丙基胺进行立体化学分配，并提出了过渡态模型来解释选择性。