1-bromo-2-(tert-butoxycarbonyl)amino-2-phenyl ethane | 478538-80-6

• 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: 1-bromo-2-(tert-butoxycarbonyl)amino-2-phenyl ethane
• 英文别名: Carbamic acid, (2-bromo-1-phenylethyl)-, 1,1-dimethylethyl ester；tert-butyl N-(2-bromo-1-phenylethyl)carbamate
• CAS: 478538-80-6
• 化学式: C₁₃H₁₈BrNO₂
• 分子量: 300.195
• InChiKey: CISQKOWVTCOHDF-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：

  1-bromo-2-(tert-butoxycarbonyl)amino-2-phenyl ethane 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 (+/-)-2-bromo-1-phenyl-ethylamine; hydrochloride
  参考文献：
  名称：

  Ionic addition of t-butyl N,N-dibromocarbamate (BBC) to alkenes and cycloalkenes

  摘要：

  The addition of t-butyl N,N-dibromocarbamate (BBC) to alkenes and cycloalkenes in the presence of BF3.Et2O proceeds smoothly at -20degreesC in CH2Cl2 affording upon reduction with aqueous Na2SO3 the corresponding beta-bromo-N-Bocamines. Immediate deprotection of these adducts with gaseous HCl yields beta-bromoamine hydrochlorides in moderate yields. The regioselectivity typical for Markovnikov addition was observed for styrene. Stereospecific anti-addition of BBC to cyclohexene and (E)-hex-3-ene, as proven by H-1 NMR evidence, is compatible with an ionic addition pathway and can be rationalized by assuming the intermediate complex formation between BBC and BF3. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.040
• 作为产物：
  描述：

  苯乙烯 、 t-butyl N,N-dibromocarbamate 在 三氟化硼乙醚 、 sodium sulfite 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到1-bromo-2-(tert-butoxycarbonyl)amino-2-phenyl ethane
  参考文献：
  名称：

  Ionic addition of t-butyl N,N-dibromocarbamate (BBC) to alkenes and cycloalkenes

  摘要：

  The addition of t-butyl N,N-dibromocarbamate (BBC) to alkenes and cycloalkenes in the presence of BF3.Et2O proceeds smoothly at -20degreesC in CH2Cl2 affording upon reduction with aqueous Na2SO3 the corresponding beta-bromo-N-Bocamines. Immediate deprotection of these adducts with gaseous HCl yields beta-bromoamine hydrochlorides in moderate yields. The regioselectivity typical for Markovnikov addition was observed for styrene. Stereospecific anti-addition of BBC to cyclohexene and (E)-hex-3-ene, as proven by H-1 NMR evidence, is compatible with an ionic addition pathway and can be rationalized by assuming the intermediate complex formation between BBC and BF3. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.040

文献信息

• Novel phenylalkyl diamine and amide analogs
  申请人：——

  公开号：US20030105079A1

  公开（公告）日：2003-06-05

  The present invention relates to novel 1,2- or 1,3-diamine and amide compounds and pharmaceutically useful salts thereof and methods for treating central nervous system diseases. The present 1,2- or 1,3-diamine and amide compounds have high binding affinity to the sigma receptor.

  本发明涉及新型的1,2-或1,3-二胺和酰胺化合物及其具有药用价值的盐，并提供了治疗中枢神经系统疾病的方法。本发明的1,2-或1,3-二胺和酰胺化合物具有高亲和力与sigma受体结合。
• US7078537B2
  申请人：——

  公开号：US7078537B2

  公开（公告）日：2006-07-18
• Ionic addition of t-butyl N,N-dibromocarbamate (BBC) to alkenes and cycloalkenes
  作者：Anna Śliwińska、Andrzej Zwierzak

  DOI：10.1016/j.tetlet.2003.10.040

  日期：2003.12

  The addition of t-butyl N,N-dibromocarbamate (BBC) to alkenes and cycloalkenes in the presence of BF3.Et2O proceeds smoothly at -20degreesC in CH2Cl2 affording upon reduction with aqueous Na2SO3 the corresponding beta-bromo-N-Bocamines. Immediate deprotection of these adducts with gaseous HCl yields beta-bromoamine hydrochlorides in moderate yields. The regioselectivity typical for Markovnikov addition was observed for styrene. Stereospecific anti-addition of BBC to cyclohexene and (E)-hex-3-ene, as proven by H-1 NMR evidence, is compatible with an ionic addition pathway and can be rationalized by assuming the intermediate complex formation between BBC and BF3. (C) 2003 Elsevier Ltd. All rights reserved.