t-butyl N,N-dibromocarbamate | 358365-86-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: t-butyl N,N-dibromocarbamate
• 英文别名: tert-butyl dibromocarbamate；Carbamic acid, N,N-dibromo-, 1,1-dimethylethyl ester；tert-butyl N,N-dibromocarbamate
• CAS: 358365-86-3
• 化学式: C₅H₉Br₂NO₂
• 分子量: 274.94
• InChiKey: KCXLLRXVLYZWSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  t-butyl N,N-dibromocarbamate 在 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 tert-butyl 2-butylaziridine-1-carboxylate
  参考文献：
  名称：

  在末端氮丙啶中锂化诱导的从氮到碳的迁移。

  摘要：

  DOI：

  10.1002/anie.200604920
• 作为产物：
  描述：

  氨基甲酸叔丁酯 在 溴 、 potassium carbonate 作用下， 以 水 为溶剂， 反应 2.0h， 生成 t-butyl N,N-dibromocarbamate
  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
• 作为试剂：
  描述：

  甲基苯乙烯 在 t-butyl N,N-dibromocarbamate 、 sodium sulfite 、 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.33h， 生成 、
  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

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。
• TETRAHYDRO-PYRAN DERIVATIVES
  申请人：Kolczewski Sabine

  公开号：US20110190349A1

  公开（公告）日：2011-08-04

  The present invention relates to a compound of formula I wherein R 1 /R 2 are independently from each other hydrogen, (CR 2 ) o -cycloalkyl, optionally substituted by lower alkyl or hydroxy, or are lower alkyl or heterocycloalkyl, and o is 0 or 1; and R may be the same or different and is hydrogen or lower alkyl; or R 1 and R 2 may form together with the N atom to which they are attached a heterocycloalkyl group, selected from the group consisting of pyrrolidinyl, piperidinyl, 3-aza-bicyclo[3.1.0]hex-3-yl or 2-aza-bicyclo[3.1.0]hex-2-yl, which are optionally substituted by hydroxy; R 3 is S-lower alkyl, lower alkyl, lower alkoxy or cycloalkyl; R 3′ is hydrogen, lower alkyl substituted by halogen, lower alkyl or lower alkoxy R 4 is lower alkyl substituted by halogen, lower alkyl or lower alkoxy; X is —O— or —CH 2 —; X′ is —O— or —CH 2 —; with the proviso that one of X or X′ is always —O— and the other is —CH 2 —; or to a pharmaceutically acceptable acid addition salt, to a racemic mixture, or to its corresponding enantiomer and/or optical isomer thereof. It has been found that the compounds of formula I are good inhibitors of the glycine transporter 1 (GlyT-1) and therefore they may be used for the treatment of schizophrenia.

  本发明涉及一种化合物，其化学式为I，其中R1/R2独立地为氢、(CR2)o-环烷基，可选择地被较低的烷基或羟基取代，或者为较低的烷基或杂环烷基，o为0或1；而R可能相同也可能不同，为氢或较低的烷基；或者R1和R2可以与它们连接的N原子一起形成一个杂环烷基基团，选自吡咯烷基、哌啶基、3-氮杂双环[3.1.0]己基或2-氮杂双环[3.1.0]己基，可选择地被羟基取代；R3为S-较低的烷基、较低的烷基、较低的烷氧基或环烷基；R3'为氢、被卤素取代的较低的烷基、较低的烷基或较低的烷氧基；R4为被卤素取代的较低的烷基、较低的烷基或较低的烷氧基；X为—O—或—CH2—；X'为—O—或—CH2—；但其中X或X'中的一个始终为—O—，另一个为—CH2—；或者为药学上可接受的酸加合盐，为外消旋混合物，或为其对应的对映体和/或光学异构体。已发现，化合物I的抑制甘氨酸转运蛋白1（GlyT-1）的效果良好，因此可用于治疗精神分裂症。
• [EN] TETRAHYDRO-PYRAN DERIVATIVES AGAINST NEUROLOGICAL ILLNESSES<br/>[FR] DÉRIVÉS DE TÉTRAHYDROPYRANE DIRIGÉS CONTRE DES MALADIES NEUROLOGIQUES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2011095434A1

  公开（公告）日：2011-08-11

  The present invention relates to a compound of general formula (I) wherein X is -O- or -CH2-; X' is -O- or -CH2-; with the proviso that one of X or X' is always -O- and the other is -CH2-.It has been found that the compounds of general formula (I) are good inhibitors of the glycine transporter 1 (GIyT-1) and therefore they may be used for the treatment of schizophrenia, psychoses and other neurological conditions, including pain.

  本发明涉及一种通式(I)的化合物，其中X为-O-或-CH2-；X'为-O-或-CH2-；但其中一者为-O-，另一者为-CH2-。已发现通式(I)的化合物是甘氨酸转运体1（GIyT-1）的良好抑制剂，因此它们可以用于治疗精神分裂症、精神病和其他神经疾病，包括疼痛。
• A Metal-Free Three-Component Reaction of <i>trans</i>-β-Nitrostyrene Derivatives, Dibromo Amides, and Amines Leading to Functionalized Amidines
  作者：Meng Zhou、Jinlei Li、Chao Tian、Xiao Sun、Xiaoting Zhu、Yaohang Cheng、Guanghui An、Guangming Li

  DOI：10.1021/acs.joc.8b02998

  日期：2019.1.18

  metal-free, and multicomponent route for the preparation of N-acyl amidines from nitroalkene derivatives, dibromo amides, and amines has been developed that accesses an initial α,α-dibromonitroalkane intermediate that can undergo C–C bond cleavage. This protocol offers an alternative approach toward N-acyl amidines and features the rapid construction of amidine frameworks with high diversity and complexity

  从硝基烯烃衍生物，二溴酰胺和胺制备N-酰基am的温和，无金属，多组分途径已得到开发，该方法可使用初始的可经历C-C键断裂的α，α-二溴硝基烷中间体。该协议为N-酰基am提供了另一种方法，并具有快速构建具有高度多样性和复杂性的idine构架的特点。该方法还可以得到双am和α，β-不饱和am，它们是传统方法的挑战性靶标。
• Approach to Vicinal <i>t</i>-Boc-amino Dibromides via Catalytic Aminobromination of Nitrostyrenes without Using Chromatography and Recrystallization
  作者：Hao Sun、Jianlin Han、Padmanabha V. Kattamuri、Yi Pan、Guigen Li

  DOI：10.1021/jo302727v

  日期：2013.2.1

  A 1.0 mol % amount of K3PO4 center dot 3H(2)O was found to catalyze aminohalogenation reaction of nitrostyrenes with N,N-dibromo-tert-butylcarbamate (t-Boc-NBr2) in a dichloroethane system. Good to excellent yields and complete regioselectivity have been achieved by taking advantage of the GAP workup without using traditional purification techniques such as column chromatography and recrystallization. A new mechanism is proposed involving radical and ionic catalytic cycles and an intramolecular migration.