(3,5-dinitrophenyl)(2-methylaziridin-1-yl)methanone | 63378-99-4

• 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: (3,5-dinitrophenyl)(2-methylaziridin-1-yl)methanone
• 英文别名: (3,5-Dinitrophenyl)-(2-methylaziridin-1-yl)methanone
• CAS: 63378-99-4
• 化学式: C₁₀H₉N₃O₅
• 分子量: 251.199
• InChiKey: OXIFHJWXWLUEQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  428.6±35.0 °C(Predicted)
• 密度：
  1.522±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3,5-dinitrophenyl)(2-methylaziridin-1-yl)methanone 在 三苯基硼酸酯 、 (R)-1,1'-Bi-2-naphthol 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以49%的产率得到(R)-(3,5-dinitrophenyl)(2-methylaziridin-1-yl)methanone
  参考文献：
  名称：

  N-酰基氮丙啶的对映选择性合成和立体选择性开环

  摘要：

  动力学拆分的Ñ通过亲核开环，用（实现-acylaziridines - [R）-BINOL硼催化的条件下，所述手性改性剂（; Ar为3,5-二硝基苯基参见方案）。消耗的氮丙啶对映体可以进一步转化为对映体富集的1,2-氯酰胺，同时回收（R）-BINOL。

  DOI：

  10.1002/anie.201204224
• 作为产物：
  描述：

  3,5-二硝基苯甲酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 19.0h， 生成 (3,5-dinitrophenyl)(2-methylaziridin-1-yl)methanone
  参考文献：
  名称：

  Scalable Synthesis of N-Acylaziridines from N-Tosylaziridines

  摘要：

  N-Acylaziridines are important starting materials for the synthesis of chiral amine derivatives. The traditional methods for producing these activated aziridines have significant drawbacks. The gram scale synthesis of N-acylaziridines by deprotection of N-tosylaztridines and reprotection with N-hydroxysuccinimide derivatives is described. Mono- and disubstituted aziridines perform well, with complete retention of stereochemical purity. The consistently moderate yields are linked to the N-tosylaziridine deprotection step, while acylation with N-hydroxysuccinimide derivatives is highly efficient.

  DOI：

  10.1021/jo401267j

文献信息

• Enantiospecific Synthesis of β-Substituted Tryptamines
  作者：Heather N. Rubin、Kinney Van Hecke、Jonathan J. Mills、Jennifer Cockrell、Jeremy B. Morgan

  DOI：10.1021/acs.orglett.7b02474

  日期：2017.9.15

  interest for development as small molecule therapeutics. The ring opening of aziridines with indoles is a powerful method for tryptamine synthesis where isomer formation can be controlled. 3,5-Dinitrobenzoyl (DNB)-protected aziridines undergo regioselective, enantiospecific ring opening to produce β-substituted tryptamines for a series of indoles. Attack at the more substituted aziridine carbon occurs in

  功能化的色胺是发展为小分子治疗剂的目标靶标。氮丙啶与吲哚的开环是一种用于色胺合成的有效方法，可控制异构体的形成。3,5-二硝基苯甲酰基（DNB）保护的氮丙啶经历区域选择性，对映体特异性开环，以生成一系列吲哚的β-取代色胺。对更多取代的氮丙啶碳的攻击以类似于S N 2的方式发生，以产生作为合成前体的DNB-色胺。
• Phosphine-Catalyzed Heine Reaction
  作者：Allen Martin、Kathleen Casto、William Morris、Jeremy B. Morgan

  DOI：10.1021/ol202410v

  日期：2011.10.21

  Aziridines are important synthetic Intermediates which readily undergo ring-opening reactions. It is demonstrated that electron-rich phosphines are efficient catalysts for the regioselective rearrangement of N-acylaziridines to oxazolines. The reactions occur in excellent yield under neutral conditions. Evidence is provided for an addition/elimination mechanism by generation of a phosphonium intermediate. Similar intermediates may be useful for the development of alternate aziridine ring-opening processes and stereoselective synthesis with enantiopure phosphines.