benzyl N-benzyl-N-(1-phenyl-3-butenyl)carbamate | 470678-04-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl N-benzyl-N-(1-phenyl-3-butenyl)carbamate
• 英文别名: benzyl N-benzyl-N-(1-phenylbut-3-enyl)carbamate
• CAS: 470678-04-7
• 化学式: C₂₅H₂₅NO₂
• 分子量: 371.479
• InChiKey: FLFVHQDNLWKAPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzyl N-benzyl-N-(1-phenyl-3-butenyl)carbamate 在 正丁基锂 、 二氯二茂锆 作用下， 生成 (3RS,5RS)-1-benzyl-3-methyl-5-phenylpyrrolidin-2-one 、 (3SR,5RS)-1-benzyl-3-methyl-5-phenylpyrrolidin-2-one
  参考文献：
  名称：

  Asymmetric synthesis of di- and trisubstituted pyrrolidinones via zirconium-mediated intramolecular coupling of N-3-alkenyl carbamates

  摘要：

  N-3-Alkenyl carbamates, which are readily available in enantiomerically pure form, undergo a stereoselective intramolecular coupling under the effect of a Cp2ZrCl2/2n-BuLi reagent. The influence of the carbamate structure on the stereoselectivity was tested. The reaction gives an easy access to various di-and trisubstituted enantiopure pyrrolidinones. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.026
• 作为产物：
  描述：

  n-苄基苯甲酰胺 在 吡啶 、 正丁基锂 、 三氟化硼乙醚 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 benzyl N-benzyl-N-(1-phenyl-3-butenyl)carbamate
  参考文献：
  名称：

  无环酰胺向α-烷基化胺的通用转化。

  摘要：

  已经开发了一种通用且有效的方法，用于通过N，O-缩醛TMS醚（一种出色的N-酰基酰亚胺离子的前体）对无环酰胺进行通用官能化。

  DOI：

  10.1039/b201719a

文献信息

• Diastereoselective synthesis of 6-functionalized 4-aryl-1,3-oxazinan-2-ones and their application in the synthesis of 3-aryl-1,3-aminoalcohols and 6-arylpiperidine-2,4-diones
  作者：Sven Mangelinckx、Yahya Nural、H. Ali Dondas、Bram Denolf、Reijo Sillanpää、Norbert De Kimpe

  DOI：10.1016/j.tet.2010.03.113

  日期：2010.6

  Halocyclocarbamation of benzyl N-(1-phenyl-3-butenyl)carbamates afforded 6-functionalized 4-aryl-1,3-oxazinan-2-ones with moderate to excellent diastereoselectivity depending on the N-substituent. Importantly, in contrast to reported cyclocarbamations of homoallylic carbamates, which are generally trans-diastereoselective, cyclization of N-unsubstituted Cbz-protected homoallylamines led to cis-1,3-oxazinan-2-ones, predominantly. The use of N-benzylated and in situ prepared N-silylated derivatives resulted however in trans-selectivity. Transition states are proposed to explain the stereochemical influence of the N-substituent on the cyclocarbamations. The functionalized 1,3-oxazinan-2-ones could be further elaborated towards biologically or synthetically important 6-arylpiperidine-2,4-diones and 3-aryl-1,3-aminoalcohols. (C) 2010 Elsevier Ltd. All rights reserved.
• The versatile conversion of acyclic amides to α-alkylated amines
  作者：Young-Ger Suh、Dong-Yun Shin、Jae-Kyung Jung、Seok-Ho Kim

  DOI：10.1039/b201719a

  日期：2002.5.9

  A general and efficient method for the versatile functionalization of acyclic amide via N,O-acetal TMS ether, an excellent precursor for the N-acyliminium ion, has been developed.

  已经开发了一种通用且有效的方法，用于通过N，O-缩醛TMS醚（一种出色的N-酰基酰亚胺离子的前体）对无环酰胺进行通用官能化。
• Asymmetric synthesis of di- and trisubstituted pyrrolidinones via zirconium-mediated intramolecular coupling of N-3-alkenyl carbamates
  作者：Clément Denhez、Jean-Luc Vasse、Dominique Harakat、Jan Szymoniak

  DOI：10.1016/j.tetasy.2007.01.026

  日期：2007.2

  N-3-Alkenyl carbamates, which are readily available in enantiomerically pure form, undergo a stereoselective intramolecular coupling under the effect of a Cp2ZrCl2/2n-BuLi reagent. The influence of the carbamate structure on the stereoselectivity was tested. The reaction gives an easy access to various di-and trisubstituted enantiopure pyrrolidinones. (c) 2007 Elsevier Ltd. All rights reserved.