tert-butyl N-diethoxyphosphoryl-N-(3-phenylpropyl)carbamate | 1026842-43-2

• 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: tert-butyl N-diethoxyphosphoryl-N-(3-phenylpropyl)carbamate
• CAS: 1026842-43-2
• 化学式: C₁₈H₃₀NO₅P
• 分子量: 371.414
• InChiKey: RGJKKFCBTCLYBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对甲苯磺酸 、 tert-butyl N-diethoxyphosphoryl-N-(3-phenylpropyl)carbamate 以 乙醇 为溶剂， 反应 6.0h， 以61%的产率得到Toluene-4-sulfonic acid; compound with 3-phenyl-propylamine
  参考文献：
  名称：

  An Optimized Version of Gabriel-Type Nucleophilic Amination

  摘要：

  N-Alkylation of primary alkyl bromides with diethyl N-sodio-N-(t-butoxycarbonyl)phosphoramidate 1 carried out in boiling acetonitrile in the presence of 10mol% of tetrabutylammonium bromide as catalyst leads to the corresponding N-alkyl derivatives 2a-1. Deprotection of 2 by refluxing with p-toluenesulfonic acid in ethanol affords ammonium tosylates 3a-1 in reasonable yields.

  DOI：

  10.1080/00397910008086868
• 作为产物：
  描述：

  1-溴-3-苯基丙烷 、 Diethyl N-sodio-N-(tert-butoxycarbonyl)phosphoramidate 在 四丁基溴化铵 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 tert-butyl N-diethoxyphosphoryl-N-(3-phenylpropyl)carbamate
  参考文献：
  名称：

  An Optimized Version of Gabriel-Type Nucleophilic Amination

  摘要：

  N-Alkylation of primary alkyl bromides with diethyl N-sodio-N-(t-butoxycarbonyl)phosphoramidate 1 carried out in boiling acetonitrile in the presence of 10mol% of tetrabutylammonium bromide as catalyst leads to the corresponding N-alkyl derivatives 2a-1. Deprotection of 2 by refluxing with p-toluenesulfonic acid in ethanol affords ammonium tosylates 3a-1 in reasonable yields.

  DOI：

  10.1080/00397910008086868

文献信息

• NEW PROTOCOL FOR CONVERTING ALCOHOLS INTO AMINES
  作者：Anna Klepacz、Andrzej Zwierzak

  DOI：10.1081/scc-100103987

  日期：2001.1

  The reactions between diethyl N-(t-butoxycarbonyl)phosphoramidate 1. diisopropyl azodicarboxylate (DIAD), triphenylphosphine (TPP) and primary or secondary alcohols lead to the corresponding diethyl N-alkyl-N-(t-butoxycarbonyl)phosphoramidates 2a-o. Deprotection of crude 2 by refluxing with p-toluenesulfonic acid monohydrate in ethanol affords ammonium tosylates 3a-o in moderate to good overall yields. The N-alkylation of 1 proceeds stereoselectively with complete inversion of the configuration of the alkyl group.
• An Optimized Version of Gabriel-Type Nucleophilic Amination
  作者：Andrzej Zwierzak

  DOI：10.1080/00397910008086868

  日期：2000.7

  N-Alkylation of primary alkyl bromides with diethyl N-sodio-N-(t-butoxycarbonyl)phosphoramidate 1 carried out in boiling acetonitrile in the presence of 10mol% of tetrabutylammonium bromide as catalyst leads to the corresponding N-alkyl derivatives 2a-1. Deprotection of 2 by refluxing with p-toluenesulfonic acid in ethanol affords ammonium tosylates 3a-1 in reasonable yields.