N-Boc-2-bromohexylamine | 358365-99-8

• 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-Boc-2-bromohexylamine
• 英文别名: tert-butyl N-(2-bromohexyl)carbamate
• CAS: 358365-99-8
• 化学式: C₁₁H₂₂BrNO₂
• 分子量: 280.205
• InChiKey: JKOPHBHAFRPYOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 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-bromohexylamine 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-bromohexylamine hydrochloride
  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
• 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-bromohexylamine
  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

• Dimerization and Isomerization Reactions of α-Lithiated Terminal Aziridines
  作者：David M. Hodgson、Philip G. Humphreys、Steven M. Miles、Christopher A. J. Brierley、John G. Ward

  DOI：10.1021/jo701901t

  日期：2007.12.1

  The scope of dimerization and isomerization reactions of α-lithiated terminal aziridines is detailed. Regio- and stereoselective deprotonation of simple terminal aziridines with lithium 2,2,6,6-tetramethylpiperidide (LTMP) or lithium dicyclohexylamide (LiNCy2) generates trans-α-lithiated terminal aziridines. These latter species can then undergo dimerization or isomerization reactions depending on

  详细描述了α-锂化的末端氮丙啶的二聚和异构化反应的范围。用2,2,6,6-四甲基哌啶锂（LTMP）或二环己酰胺锂（LiNCy 2）对简单的末端氮丙啶进行区域和立体选择性去质子化，生成反式-α-锂化的末端氮丙啶。然后，根据N-保护基团的性质，这些后面的物质可以进行二聚或异构化反应。带有N-烷氧羰基（Boc）保护的α-锂化的末端氮丙啶经过N-到C- [1,2]的迁移，得到NH反式-叠氮基酯。相反，带有N-有机磺酰基的氮丙啶[叔丁基磺酰基（Bus）]保护剂进行快速二聚，生成2-烯-1,4-二胺；如果存在侧链烯烃，则进行非对映选择性环丙烷化，生成2-氨基双环[3.1.0]己烷。所有这些反应都被用作制备合成和生物学重要靶标的关键步骤。
• 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.
• Lithiation-Induced Migrations from Nitrogen to Carbon in Terminal Aziridines
  作者：David M. Hodgson、Philip G. Humphreys、Zhaoqing Xu、John G. Ward

  DOI：10.1002/anie.200604920

  日期：2007.3.19