1-(4-bromobenzyl)-2-(bromomethyl)aziridine | 497239-65-3

• 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-(4-bromobenzyl)-2-(bromomethyl)aziridine
• 英文别名: 1-(4-Bromo-benzyl)-2-bromomethyl-aziridine；2-(bromomethyl)-1-[(4-bromophenyl)methyl]aziridine
• CAS: 497239-65-3
• 化学式: C₁₀H₁₁Br₂N
• 分子量: 305.012
• InChiKey: DNBZZDVFUSNFDL-UHFFFAOYSA-N

物化性质

• 沸点：
  324.9±17.0 °C(Predicted)
• 密度：
  1.762±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-bromobenzyl)-2-(bromomethyl)aziridine 在 magnesium 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以70%的产率得到N-(4-溴苄基)-2-丙烯-1-胺
  参考文献：
  名称：

  Electron transfer induced ring opening of 2-(bromomethyl)aziridines by magnesium in methanol

  摘要：

  Magnesium metal in methanol was used as a simple electron transfer induced ring-opening reagent of 2-(bromomethyl)aziridines to afford allylamines derivatives in 70-90% yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00728-7
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到1-(4-bromobenzyl)-2-(bromomethyl)aziridine
  参考文献：
  名称：

  Electron transfer induced ring opening of 2-(bromomethyl)aziridines by magnesium in methanol

  摘要：

  Magnesium metal in methanol was used as a simple electron transfer induced ring-opening reagent of 2-(bromomethyl)aziridines to afford allylamines derivatives in 70-90% yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00728-7

文献信息

• Synthesis of 2-[(Arylmethylene)amino]cyclopropanecarbonitriles via a Two-Step Ring Transformation of 2-(Cyanomethyl)aziridines
  作者：Norbert De Kimpe、Sven Mangelinckx、Matthias D’hooghe、Sietske Peeters

  DOI：10.1055/s-0028-1088000

  日期：2009.4

  Reaction of 2-(cyanomethyl)aziridines with N-bromosuccinimide in dichloromethane results in the formation of 3-[(arylmethylene)amino]-4-bromobutanenitriles in high yield. The latter β-amino-γ-bromobutanenitriles were converted into separable trans- and cis-2-[(arylmethylene)amino]cyclopropanecarbonitriles through a 1,3-cyclization by reaction with potassium tert-butoxide, thus culminating in a two-step ring transformation of 2-(cyano­methyl)aziridines into 2-[(arylmethylene)amino]cyclopropanecarbonitriles.

  2-(氰基甲基)氮杂环丁烯与N-溴琥珀酰亚胺在二氯甲烷中的反应生成高收率的3-[(芳烯基)氨基]-4-溴丁腈。后者的β-氨基-γ-溴丁腈通过与醋酸钾的反应进行1,3-环化，转化为可分离的反式和顺式2-[(芳烯基)氨基]环丙烷碳腈，从而完成了2-(氰基甲基)氮杂环丁烯到2-[(芳烯基)氨基]环丙烷碳腈的两步环转化。
• Synthesis of 1-Arylmethyl-2-(cyanomethyl)aziridines and Their Ring Transformation into Methyl <i>N</i>-(2-Cyanocyclopropyl)benzimidates
  作者：Matthias D'hooghe、Sven Mangelinckx、Evelien Persyn、Willem Van Brabandt、Norbert De Kimpe

  DOI：10.1021/jo060425p

  日期：2006.5.1

  α-dichlorobenzyl)amino)butanenitriles with sodium methoxide in methanol resulted in novel methyl N-(2-chloro-1-(cyanomethyl)ethyl)benzimidates, although in low yields. The latter γ-chloro nitriles were smoothly converted into methyl N-(2-cyanocyclopropyl)benzimidates as precursors of biologically relevant β-ACC derivatives through a 1,3-cyclization protocol by reaction with potassium tert-butoxide in THF

  在DMSO中用氰化钾处理后，可以由相应的2-（溴甲基）氮丙啶高产率地制备1-芳基甲基-2-（氰基甲基）氮丙啶。在CCl 4中用N-氯琥珀酰亚胺将氮丙啶部分开环，然后在甲醇中用甲醇钠处理由此形成的4-氯-3-（N-氯-N-（α，α-二氯苄基）氨基）丁腈。新颖甲基ñ - （2-氯-1-（氰基甲基）乙基）benzimidates，虽然在低的产率。后者的γ-氯腈通过与钾反应的1,3-环化方案被平滑地转化为N-（2-氰基环丙基）苯并亚甲基丙烯酸酯作为生物相关的β-ACC衍生物的前体在THF中的叔丁醇盐。
• New Synthesis of Propargylic Amines from 2-(Bromomethyl)aziridines. Intermediacy of 3-Bromoazetidinium Salts
  作者：Matthias D'hooghe、Willem Van Brabandt、Norbert De Kimpe

  DOI：10.1021/jo035759i

  日期：2004.4.1

  propargylamines in high overall yields (64−77%) by transformation of 1-(arylmethyl)-2-(bromomethyl)aziridines into N,N-di(arylmethyl)-N-(2-propynyl)amines via N-(2,3-dibromopropyl)amines and N-(2-bromo-2-propenyl)amines. The conversion of N-(2,3-dibromopropyl)amines into N-(2-bromo-2-propenyl)amines is based on a novel analogue of the Hofmann elimination. A Yamaguchi−Hirao alkylation, a Sonogashira

  通过将1-（芳甲基）-2-（溴甲基）氮丙啶转化为N，N-二（芳甲基）-N-（2-炔丙基）胺通过N-（2,3-二溴丙基）胺和N-（2-溴-2-丙烯基）胺。的转化ñ - （2,3-二溴丙基）胺成ñ - （2-溴-2-丙烯基）胺是基于霍夫曼消除反应的新型类似物。Yamaguchi-Hirao烷基化，Sonogashira偶联或加氢芳基化反应将这些炔丙基胺进一步官能化，成为可能有趣的化合物，可用于医药和农业化学用途。
• Novel Synthesis of <i>cis</i>-3,5-Disubstituted Morpholine Derivatives
  作者：Matthias D'hooghe、Tim Vanlangendonck、Karl W. Törnroos、Norbert De Kimpe

  DOI：10.1021/jo060313y

  日期：2006.6.1

  using bromine in dichloromethane. The latter morpholine has been used as a substrate for the synthesis of the corresponding 3,5-di(methoxymethyl)morpholine and 3,5-di(cyanomethyl)morpholine upon nucleophilic displacement of both bromo atoms. Further evaluation of this protocol toward the synthesis of 4-arylmethyl- and 4-alkylmethyl-3,5-di(bromomethyl)morpholines showed that the premised cyclization of the

  1-叔丁基-2-（烯丙氧基甲基）氮丙啶已首次使用苯在二氯甲烷中的亲电试剂诱导的闭环反应非对映选择性地转化为顺式-3,5-二（溴甲基）-4-叔丁基吗啉。后者的吗啉已被用作在两个溴原子亲核取代后合成相应的3,5-二（甲氧基甲基）吗啉和3,5-二（氰基甲基）吗啉的底物。对该协议对4-芳基甲基和4-烷基甲基-3,5-二（溴甲基）吗啉的合成的进一步评估表明，将相应的2-（烯丙氧基甲基）氮丙啶以3,5-二（溴甲基）为前提的环化反应吗啉仅在N上进行良好-新戊基吗啉，随后将其转化为3-氧杂-7-硫杂-9-氮杂双环[3.3.1]壬烷衍生物。同样，在某些其他情况下，所需的3,5-二（溴甲基）吗啉以低收率分离并转化为相应的3,5-二（氰甲基）吗啉。
• Synthesis of quaternary allylammonium salts via ring opening of 1-benzyl-2-(bromomethyl)aziridines
  作者：Matthias D'hooghe、Willem Van Brabandt、Norbert De Kimpe

  DOI：10.1016/s0040-4020(03)00771-3

  日期：2003.7

  Treatment of 1-benzyl-2-(bromomethyl)aziridine, and some aryl substituted analogues, with an excess of iodomethane resulted in N-allyl-N-benzyl-N,N-dimethylammonium salts, in good yields. These quaternary allylammonium salts are of importance in different fields, from organic synthesis and polymeric chemistry to agricultural use. (C) 2003 Elsevier Science Ltd. All rights reserved.