N-Boc-2-bromo-2-phenylethylamine | 358365-87-4

• 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: N-Boc-2-bromo-2-phenylethylamine
• 英文别名: Tert-butyl (2-bromo-2-phenylethyl)carbamate；tert-butyl N-(2-bromo-2-phenylethyl)carbamate
• CAS: 358365-87-4
• 化学式: C₁₃H₁₈BrNO₂
• 分子量: 300.195
• InChiKey: CFYGNZZNXHSSEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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-Boc-2-bromo-2-phenylethylamine 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以88%的产率得到2-bromo-2-phenylethylamine hydrochloride
  参考文献：
  名称：

  Regioselective aminobromination of terminal alkenes

  摘要：

  The addition of t-butyl N,N-dibromocarbamate (BBC) to a variety of terminal alkenes has been studied. The reaction was spontaneously initiated and proceeded smoothly in refluxing dichloromethane. The N-bromo adducts, formed upon addition, could be reduced in situ with aqueous sodium sulfite to give the corresponding 2-bromo-N-Boc-amines. Immediate deprotection of these compounds with gaseous HCl or p-toluenesulfonic acid afforded 2-bromoamine hydrochlorides or tosylates in pure state and good overall yields. The observed regioselectivity for anti-Markovnikov addition, as proven by NMR and MS, is fully consistent with the radical-chain mechanism proposed for the reaction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00907-4
• 作为产物：
  描述：

  t-butyl N,N-dibromocarbamate 在 水 、 sodium sulfite 作用下， 以 二氯甲烷 为溶剂， 生成 N-Boc-2-bromo-2-phenylethylamine
  参考文献：
  名称：

  t-Butyl N,N-dibromocarbamate (BBC)—new reagent for aminobromination of terminal alkenes

  摘要：

  t-Butyl N,N-dibromocarbamate, easily obtained by bromination of t-butyl carbamate in aqueous potassium carbonate, reacts smoothly with a variety of terminal alkenes to afford the corresponding beta -bromo-N-Boc-amines upon reduction with aqueous sodium sulphite. Immediate deprotection of N-Boc-amines with gaseous HCl yields beta -bromoamine hydrochlorides in good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00662-1

文献信息

• Regioselective aminobromination of terminal alkenes
  作者：Anna Śliwińska、Andrzej Zwierzak

  DOI：10.1016/s0040-4020(03)00907-4

  日期：2003.7

  The addition of t-butyl N,N-dibromocarbamate (BBC) to a variety of terminal alkenes has been studied. The reaction was spontaneously initiated and proceeded smoothly in refluxing dichloromethane. The N-bromo adducts, formed upon addition, could be reduced in situ with aqueous sodium sulfite to give the corresponding 2-bromo-N-Boc-amines. Immediate deprotection of these compounds with gaseous HCl or p-toluenesulfonic acid afforded 2-bromoamine hydrochlorides or tosylates in pure state and good overall yields. The observed regioselectivity for anti-Markovnikov addition, as proven by NMR and MS, is fully consistent with the radical-chain mechanism proposed for the reaction. (C) 2003 Elsevier Ltd. All rights reserved.
• t-Butyl N,N-dibromocarbamate (BBC)—new reagent for aminobromination of terminal alkenes
  作者：Anna Klepacz、Andrzej Zwierzak

  DOI：10.1016/s0040-4039(01)00662-1

  日期：2001.7

  t-Butyl N,N-dibromocarbamate, easily obtained by bromination of t-butyl carbamate in aqueous potassium carbonate, reacts smoothly with a variety of terminal alkenes to afford the corresponding beta -bromo-N-Boc-amines upon reduction with aqueous sodium sulphite. Immediate deprotection of N-Boc-amines with gaseous HCl yields beta -bromoamine hydrochlorides in good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.