cis-2,3-dimethylaziridine | 930-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丙烷
• 英文名称: cis-2,3-dimethylaziridine
• 英文别名: (2S,3R)-2,3-dimethylaziridine
• CAS: 930-19-8
• 化学式: C₄H₉N
• 分子量: 71.1222
• InChiKey: DNPSMEGHIHDFAJ-ZXZARUISSA-N

物化性质

• 沸点：
  81.1-81.5 °C(Press: 739 Torr)
• 密度：
  0.796±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cis-2,3-dimethylaziridine 在 氨 、 水 作用下， 生成 rac-2,3-diaminobutane
  参考文献：
  名称：

  Stereochemistry of the Opening of the Imine Ring with Ethylamine^1,2

  摘要：

  DOI：

  10.1021/ja01560a064
• 作为产物：
  描述：

  threo-2-Azido-3-iodobutane 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以84%的产率得到cis-2,3-dimethylaziridine
  参考文献：
  名称：

  The conversion of an aziridine to a .beta.-lactam

  摘要：

  DOI：

  10.1021/jo00296a070

文献信息

• Aziridine ring expansion sequences
  作者：A. Hassner、Susan S. Burke

  DOI：10.1016/s0040-4020(01)97420-4

  日期：1974.1

  β-Chloroamine hydrochlorides, produced stereospecifically and regiospecifically from aziridines with anhydrous hydrogen chloride in ether, are condensed with sodium carbonate in dry DMSO to afford isomerically pure 2-oxazolidinones.

  用无水氯化氢在乙醚中从氮丙啶立体定向和区域特异性生成的β-氯胺盐酸盐与碳酸钠在干燥的DMSO中缩合，得到异构纯的2-恶唑烷酮。
• 2-Cyclopropylindoloquinones and Their Analogues as Bioreductively Activated Antitumor Agents:  Structure−Activity <i>in Vitro</i> and Efficacy <i>in Vivo</i>
  作者：Matthew A. Naylor、Mohammed Jaffar、John Nolan、Miriam A. Stephens、Susan Butler、Kantilal B. Patel、Steven A. Everett、Gerald E. Adams、Ian J. Stratford

  DOI：10.1021/jm9608422

  日期：1997.7.1

  2-cyclopropyl and 5-(2-methylaziridinyl) derivatives, and of these, 5-(aziridin-1-yl)-2-cyclopropyl-3-(hydroxymethyl)-1-methylindole-4 ,7-dione (21) and 3-(hydroxymethyl)-5-(2-methylaziridin-1-yl)-1,2-dimethylindole+ ++-4,7-dione (54) were evaluated in vivo. Both compounds showed antitumor activity both as single agents and in combination with radiation, with some substantial improvements over EO9 (3)

  已经合成了一系列 2-环烷基-和 2-烷基-3-(羟甲基)-1-甲基吲哚醌和相应的氨基甲酸酯，并在 5 位被各种取代和未取代的氮丙啶取代。体外对缺氧细胞的细胞毒性取决于 5-氮丙啶基或 3-羟甲基类似物的取代氮丙啶基取代基的存在。5-甲氧基衍生物的活性取决于3-(氨基甲酰氧基)甲基取代基的存在。增加 2 位的空间体积会降低化合物对缺氧细胞的有效性。2-环丙基取代基比 2-异丙基取代基更有效达 2 个数量级，这表明可能导致毒性的自由基开环反应。非融合的 2-环丙基线粒体比先前报道的相关融合的环丙基线粒体更有效。醌/半醌单电子对的还原电位在-286至-380 mV范围内。半醌自由基与氧反应，速率常数为 2-8 x 10(8) dm3 mol-1 s-1。涉及双电子还原的对苯二酚在细胞毒性介导中的作用。体外最有效的化合物是 2-环丙基和 5-(2-甲基氮丙啶) 衍生物，其中 5-(氮丙啶-1-基
• Cinchona Alkaloid Amides/Dialkylzinc Catalyzed Enantioselective Desymmetrization of Aziridines with Phosphites
  作者：Masashi Hayashi、Noriyuki Shiomi、Yasuhiro Funahashi、Shuichi Nakamura

  DOI：10.1021/ja309963w

  日期：2012.11.28

  The first highly enantioselective desymmetrization of aziridines with phosphites has been developed. Excellent yields and enantio-selectivities were observed for the reaction with various aziridines using a new class of readily accessible chiral catalysts derived from 9-amino-9-deoxy-epi-cinchonas alkaloids. In studies probing the reaction mechanism, we observed some complexes for the cinchona alkaloid amide-Zn(II) by ESI-MS analysis
• Zoch, Hans-Georg; Kinzel, Elke; Szeimies, Guenter, Chemische Berichte, 1981, vol. 114, # 3, p. 968 - 974
  作者：Zoch, Hans-Georg、Kinzel, Elke、Szeimies, Guenter

  DOI：——

  日期：——
• Reactions of <i>cis</i> ‐2,3‐Dimethylaziridine, 3‐Pyrroline and Pyrrolidine with Me ₃ Al and Me ₃ Ga: Adducts and Dimeric Amides
  作者：Yuankui Zhang、Peter H. M. Budzelaar、Jan M. M. Smits、René de Gelder、Paul R. Hageman、Anton W. Gal

  DOI：10.1002/ejic.200390091

  日期：2003.2

  AbstractThe reactions of Me3Al and Me3Ga with cis‐2,3‐dimethylaziridine (1‐H), 3‐pyrroline (2‐H) and pyrrolidine (3‐H) have been investigated. At room temperature, monomeric adducts [Me3M·LH] are obtained (M = Al, Ga; L = 1−3). [Me3Al·1‐H] is the first example of a structurally characterized adduct of an aziridine and a group 13 metal. On heating in mesitylene, all adducts except [Me3Ga·2‐H] evolve methane to form the corresponding amides; the Ga complexes require somewhat higher temperatures for this reaction. In contrast to the unsubstituted aziridine derivatives (which are trimers), dimethylaziridine amides Me2M‐1 are dimers, as shown by X‐ray crystallography. NMR spectroscopic data suggest the occurrence of a cis‐trans equilibrium for these dimers in solution. For the pyrroline and pyrrolidine derivatives, the X‐ray structures suggested large changes in the C−C and C−N bond lengths on formation of the adducts and amides. However, DFT calculations reveal that these changes are artefacts, and that the real bond length changes are fairly modest. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)