tert-butyl N-[(E)-2-benzyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]-1-phenylprop-2-enyl]carbamate | 1204391-07-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: tert-butyl N-[(E)-2-benzyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]-1-phenylprop-2-enyl]carbamate
• CAS: 1204391-07-0
• 化学式: C₂₆H₃₄N₂O₄
• 分子量: 438.567
• InChiKey: XQFNCTAXPPZRCQ-DYTRJAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  tert-butyl 3-phenylprop-1-enylcarbamate 、 benzaldehyde N-boc imine 在 磷酸二苯酯 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 7.0h， 以55.556%的产率得到
  参考文献：
  名称：

  Brønsted acid-catalyzed Mannich reaction through dual activation of aldehydes and N-Boc-imines

  摘要：

  在Brønsted酸催化剂的存在下，醛和N-Boc-胺醇均被转化为烯基氨酸酯和N-Boc-亚胺盐，分别作为活化亲核试剂和电泳试剂，从而产生前所未有的Mannich加合物。

  DOI：

  10.1039/c5cc07290e

文献信息

• Brønsted acid-catalyzed Mannich reaction through dual activation of aldehydes and N-Boc-imines
  作者：Taichi Kano、Yusuke Aota、Daisuke Asakawa、Keiji Maruoka

  DOI：10.1039/c5cc07290e

  日期：——

  In the presence of a Brønsted acid catalyst, both aldehydes and N-Boc-aminals were converted to enecarbamates and N-Boc-iminium salts as activated nucleophiles and electrophiles, respectively, giving unprecedented Mannich adducts.

  在Brønsted酸催化剂的存在下，醛和N-Boc-胺醇均被转化为烯基氨酸酯和N-Boc-亚胺盐，分别作为活化亲核试剂和电泳试剂，从而产生前所未有的Mannich加合物。
• Trimethylchlorosilane-promoted aza-Mannich reaction of enecarbamates and aldimines
  作者：Pengcheng Wu、Deqin Lin、Xiaoxia Lu、Li Zhou、Jian Sun

  DOI：10.1016/j.tetlet.2009.09.097

  日期：2009.12

  A trimethylchlorosilane-promoted aza-Mannich reaction is reported utilizing enecarbamates as the nucleophile and aromatic N-Boc aldimines as the electrophile. A variety of nucleophiles and electrophiles are tolerated by the reaction conditions, delivering the adduct products in excellent yields with high E-stereoselectivities. (C) 2009 Elsevier Ltd. All rights reserved.
• N-Boc-aminals as easily accessible precursors for less accessible N-Boc-imines: facile synthesis of optically active propargylamine derivatives using Mannich-type reactions
  作者：Taiga Yurino、Yusuke Aota、Daisuke Asakawa、Taichi Kano、Keiji Maruoka

  DOI：10.1016/j.tet.2016.03.076

  日期：2016.6

  We developed a facile and practical synthesis of N-Boc-aminals, which can be used as precursors for less accessible N-Boc-imines. Aminals were obtained via simple dehydration condensation reactions of t-butyl carbamate (BocNH2) and various aldehydes in acetic anhydride, followed by filtration and washing with hexane. The obtained N-Boc-alkynylaminals could be successfully applied in enantioselective

  我们开发了一种简便实用的N -Boc-氨基缩醛合成方法，可以将其用作不太容易获得的N -Boc-亚胺的前体。通过简单的脱水缩合反应，得到缩醛胺吨丁基氨基甲酸酯（BocNH 2）和在乙酸酐各种醛，随后过滤并用己烷洗涤。所获得的N -Boc-炔基laminals可以成功地用于手性磷酸催化的对映选择性曼尼希型反应，从而提供光学活性的炔丙基胺衍生物。