1-butyl-2-methyleneaziridine | 98435-24-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-butyl-2-methyleneaziridine
• 英文别名: N-butyl-2-methyleneaziridine；N-n-butylmethyleneaziridine；1-butyl-2-methylen-aziridine；1-Butyl-2-methylen-aziridin；1-Butyl-2-methylideneaziridine
• CAS: 98435-24-6
• 化学式: C₇H₁₃N
• 分子量: 111.187
• InChiKey: RIQIVIGKSCZTLT-UHFFFAOYSA-N

物化性质

• 沸点：
  150.8±10.0 °C(Predicted)
• 密度：
  0.87±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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-butyl-2-methyleneaziridine 以10%的产率得到
  参考文献：
  名称：

  ALPER, HOWARD;HAMEL, NATHALIE, TETRAHEDRON LETT., 28,(1987) N 28, 3237-3240

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(2-bromoprop-2-enyl)-N-butylamine 在 氨 、 sodium amide 作用下， 生成 1-butyl-2-methyleneaziridine
  参考文献：
  名称：

  Synthesis of N-Allylidene-alkylamines

  摘要：

  DOI：

  10.1021/ja01150a145

文献信息

• Palladium-catalyzed hydrocarbonation of methyleneaziridines with carbon pronucleophiles
  作者：Byoung Ho Oh、Itaru Nakamura、Yoshinori Yamamoto

  DOI：10.1016/s0040-4039(02)02410-3

  日期：2002.12

  The reaction of methyleneaziridine 1 with carbon pronucleophiles (2, H-CR3) proceeds smoothly in the presence of a palladium catalyst affording the corresponding hydrocarbonation products 5 in good to high yield.

  在钯催化剂的存在下，亚甲基氮丙啶1与碳原核亲核体（2，H-CR 3）的反应平稳进行，从而以高至高收率提供相应的烃化产物5。
• Regiospecific synthesis of α-methylene-β-lactams by a homogeneous palladium catalyzed ring expansion-carbonylation reaction
  作者：Howard Alper、Nathalie Hamel

  DOI：10.1016/s0040-4039(00)95481-9

  日期：1987.1

  Tetrakis(triphenylphosphine)palladium(O) [or palladium acetate and added triphenylphosphine] catalyzes the carbonylation of methyleneaziridines to α-methylene-β-lactams at room temperature and one atmosphere.

  四（三苯基膦）钯（O）[或乙酸钯和添加的三苯基膦]在室温和一种大气压下催化亚甲基氮丙啶羰基化为α-亚甲基-β-内酰胺。
• Cycloaddition of 2-Methyleneaziridines with Isocyanates Catalyzed by Tin Iodide
  作者：Hiroki Takahashi、Seiji Yasui、Shinji Tsunoi、Ikuya Shibata

  DOI：10.1002/ejoc.201201305

  日期：2013.1

  2-Methyleneaziridines proved to be good substrates for the cycloaddition with isocyanates, for which a tin iodide system, Bu2SnI2–LiI, was employed as an effective catalyst. Products were derived from N-attack of the ring-opened metalloenamine intermediate.

  2-亚甲基氮丙啶被证明是与异氰酸酯环加成的良好底物，其中碘化锡体系 Bu2SnI2-LiI 被用作有效的催化剂。产物源自开环金属烯胺中间体的 N-攻击。
• Catalytic Cycloaddition of 2-Methyleneaziridines with 1,1-Dicyanoalkenes
  作者：Hiroki Takahashi、Seiji Yasui、Shinji Tsunoi、Ikuya Shibata

  DOI：10.1021/ol500062a

  日期：2014.2.21

  2-Methyleneaziridine are a good substrate for the catalytic synthesis of cyclopentylidenamines via a [3 + 2] cycloaddition of 1,1-dicyanoalkenes using Bu2SnI2 as an effective catalyst. A C-attack from 2-methyleneaziridine yielded the desired products.
• Palladium-Catalyzed Ring-Opening Reaction of Methyleneaziridines with Carboxylic Acids:  Synthesis of α-Amidoketones
  作者：Byoung Ho Oh、Itaru Nakamura、Yoshinori Yamamoto

  DOI：10.1021/jo035739g

  日期：2004.4.1

  In the presence of palladium catalysts, the reaction of methyleneaziridines 1 with carboxylic acids 2 proceeded smoothly to give the corresponding alpha-amidoketones 3 in good to high yields.