N-Boc-2-bromo-2-methylpropylamine | 358365-97-6

• 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-bromo-2-methylpropylamine
• 英文别名: tert-butyl (1-bromo-2-methylpropan-2-yl)carbamate；tert-butyl N-(2-bromo-2-methylpropyl)carbamate
• CAS: 358365-97-6
• 化学式: C₉H₁₈BrNO₂
• 分子量: 252.151
• InChiKey: UQUXJJUPVLIZLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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-methylpropylamine 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以78%的产率得到2-bromo-2-methylpropylamine 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：

  tert-butyl N-bromo-N-(2-bromo-2-methylpropyl)carbamate 在 水 、 sodium sulfite 作用下， 生成 N-Boc-2-bromo-2-methylpropylamine
  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

• TRPM8 receptor antagonists
  申请人：Dompé S.p.A.

  公开号：EP2481727A1

  公开（公告）日：2012-08-01

  Compounds acting as selective antagonists of Transient Receptor Potential cation channel subfamily M member 8 (hereinafter referred to as TRPM8), having formula: wherein R is selected from: - H, CN, NO2, SO2NH2, SO2NHR' and SO2NR'2, where R' is selected from linear or branched C1-C4 alkyl; X is selected from: - F, Cl, CH3, NH2 and OH Y is selected from: - O, CH2, NH and SO2 R1, R2, R3 and R4, indipendently one from the other, are selected from - H and linear or branched C1-C4 alkyl; Z is selected from: - NR6 and R6R7N+, where R6 and R7 indipendently one from the other, are selected from: • H and linear or branched C1-C4 alkyl R5 is a residue selected from: - H and linear or branched C1-C4 alkyl Het is a heteroaryl group selected from - a substituted or not substituted pyrrolyl, a substituted or not substituted N-methylpyrrolyl, a substituted or not substituted thiophenyl, a substituted or not substituted furanyl and a substituted or not substituted pyridinyl. Said compounds are useful in the treatment of pathologies depending on TRPM8 activity such as pain, cancer, inflammation, ischaemia, neurodegeneration, stroke, psychiatric disorders, inflammatory conditions, urological disorders.

  作为Transient Receptor Potential阳离子通道亚家族M成员8（以下简称为TRPM8）的选择性拮抗剂的化合物，其化学式为：其中R选择自：- H、CN、NO2、SO2NH2、SO2NHR'和SO2NR'2，其中R'选择自直链或支链的C1-C4烷基；X选择自：- F、Cl、CH3、NH2和OHY选择自：- O、CH2、NH和SO2R1、R2、R3和R4，独立地选择自- H和直链或支链的C1-C4烷基；Z选择自：- NR6和R6R7N+，其中R6和R7独立地选择自：• H和直链或支链的C1-C4烷基R5是选择自：- H和直链或支链的C1-C4烷基Het是选择自：- 取代或未取代的吡咯基、取代或未取代的N-甲基吡咯基、取代或未取代的噻吩基、取代或未取代的呋喃基和取代或未取代的吡啶基。这些化合物在治疗依赖于TRPM8活性的病理病变如疼痛、癌症、炎症、缺血、神经退行性疾病、中风、精神障碍、炎症性疾病、泌尿系统疾病方面是有用的。