2[(2-bromobenzyl)oxy]aniline hydrochloride

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2[(2-bromobenzyl)oxy]aniline hydrochloride
• 英文别名: 2-[(2-Bromophenyl)methoxy]aniline;hydrochloride
• 化学式: C₁₃H₁₂BrNO*ClH
• 分子量: 314.609
• InChiKey: KPTFCTPXLWUCCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  35.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2[(2-bromobenzyl)oxy]aniline hydrochloride 在 tris(dibenzylideneacetone)dipalladium (0) 三叔丁基膦 、 potassium carbonate 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以86%的产率得到5,11-二氢二苯并[b,e][1,4]噁氮杂卓
  参考文献：
  名称：

  An Efficient Assembly of Heterobenzazepine Ring Systems Utilizing an Intramolecular Palladium-Catalyzed Cycloamination

  摘要：

  Azaheterocyclic compounds are interesting and medicinally relevant targets. Herein we disclose an improved synthesis into the oxazepine and thiazepine ring systems. The key step in the synthesis exploits recent advancements in the palladium-catalyzed amination reaction, which was utilized to form the seven-membered rings. General conditions for this reaction were Pd(2)dba(3), P(t-BU)(3), NaO-t-Bu alone or with K2CO3, in toluene. The scope of the reaction was investigated, and has been shown to be effective on a variety of substrates as illustrated.

  DOI：

  10.1021/jo026546g
• 作为产物：
  描述：

  2-bromobenzyl 2-nitrophenyl ether 在 盐酸 、 铁粉 作用下， 以 异丙醇 为溶剂， 反应 17.0h， 以80%的产率得到2[(2-bromobenzyl)oxy]aniline hydrochloride
  参考文献：
  名称：

  An Efficient Assembly of Heterobenzazepine Ring Systems Utilizing an Intramolecular Palladium-Catalyzed Cycloamination

  摘要：

  Azaheterocyclic compounds are interesting and medicinally relevant targets. Herein we disclose an improved synthesis into the oxazepine and thiazepine ring systems. The key step in the synthesis exploits recent advancements in the palladium-catalyzed amination reaction, which was utilized to form the seven-membered rings. General conditions for this reaction were Pd(2)dba(3), P(t-BU)(3), NaO-t-Bu alone or with K2CO3, in toluene. The scope of the reaction was investigated, and has been shown to be effective on a variety of substrates as illustrated.

  DOI：

  10.1021/jo026546g

文献信息

• Process for producing new oxazepine derivatives
  申请人：AJINOMOTO CO. INC

  公开号：US20020133004A1

  公开（公告）日：2002-09-19

  A process for producing a 5-substituted-5,11-dihydro-debenzo [b,e] [1,4] oxazepine compound, wherein a [2-(2-bromobenzyloxy)phenyl]amide derivative having a substituent introduced through amido bond, the substituent locating at the 5-position of the final compound, as the starting material, is subjected to the intramolecular arylation and then the obtained product is reduced. In particular, (R)-1-[(4-methoxyphenyl)acetyl]pyrrolidine-2-carboxylic acid [2-(2-bromo benzyloxy)phenyl]amide is subjected to the intramolecular arylation to obtain (R)-[[2-(5,11-dihydro-dibenzo[b,e][1,4]oxazepine-5-carbonyl)pyrrolidin]-1-yl]-2-(4-methoxyphenyl)ethanone and then this product is reduced.

  一种制备5-取代-5，11-二氢-二苯并[b，e][1,4]噁唑啉化合物的方法，其中以[R]-1-[(4-甲氧基苯基)乙酰基]吡咯烷-2-羧酸[2-(2-溴苄氧基)苯基]酰胺作为起始物质，通过分子内芳基化反应，然后还原所得产物。具体来说，将[R]-[2-(2-溴苄氧基)苯基]酰胺-[1-[(4-甲氧基苯基)乙酰基]吡咯烷-2-羧酸]经过分子内芳基化反应，得到(R)-[[2-(5,11-二氢-二苯并[b,e][1,4]噁唑啉-5-羰基)吡咯烷-1-基]-2-(4-甲氧基苯基)乙酮，然后还原该产物。
• NOVEL PROCESSES FOR PREPARING OXAZEPINE DERIVATIVES
  申请人：Ajinomoto Co., Inc.

  公开号：EP1219611A1

  公开（公告）日：2002-07-03

  A [2-(2-bromobenzyloxy)phenyl] amide derivative having a substituent introduced through amido bond, the substituent locating at the 5-position of the final compound, as the starting material, is subjected to the intramolecular arylation and then the obtained product is reduced. In particular, (R)-1-[(4-methoxyphenyl)acetyl]pyrrolidine-2-carboxylic acid [2-(2-bromo benzyloxy)phenyl]amide is subjected to the intramolecular arylation to obtain (R)-[[2-(5,11-dihydrodibenzo[b,e][1,4]oxazepine-5-carbonyl) pyrrolidin]-1-yl]-2-(4-methoxyphenyl)ethanone and then this product is reduced. This process is particularly useful for producing 5-substituted-5,11-dihydrodibenzo[b,e][1,4]oxazepine derivatives, particularly 5,11-dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo- [b,e][1,4]oxazepine, on an industrial scale.

  一种[2-(2-溴苄氧基)苯基]酰胺衍生物作为起始原料，具有通过氨基键引入的取代基，该取代基位于最终化合物的 5 位，对其进行分子内芳基化反应，然后将得到的产物还原。其中，(R)-1-[(4-甲氧基苯基)乙酰基]吡咯烷-2-羧酸[2-(2-溴苄氧基)苯基]酰胺经分子内芳基化反应得到(R)-[[2-(5、11-二氢二苯并[b,e][1,4]氧氮杂卓-5-羰基)吡咯烷]-1-基]-2-(4-甲氧基苯基)乙酮，然后将该产物还原。该工艺特别适用于工业化生产 5-取代-5,11-二氢二苯并[b,e][1,4]氧氮杂卓衍生物，尤其是 5,11-二氢-5-[1-(4-甲氧基苯乙基)-2-吡咯烷基甲基]二苯并[b,e][1,4]氧氮杂卓。
• Novel Polycyclic Heterocycles. II. Derivatives of 5,11-Dihydrodibenz[b,e][1,4]oxazepine¹
  作者：Harry L. Yale、Francis Sowinski

  DOI：10.1021/jm00335a008

  日期：1964.9