1-benzyl-2-isopropylidene-3-methylaziridine

• 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-benzyl-2-isopropylidene-3-methylaziridine
• 英文别名: 1-Benzyl-2-methyl-3-propan-2-ylideneaziridine；1-benzyl-2-methyl-3-propan-2-ylideneaziridine
• 化学式: C₁₃H₁₇N
• 分子量: 187.285
• InChiKey: LITJABBYJALVME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-(2-bromo-3-methyl-2-butenyl)-benzylamine 在 四甲基乙二胺 、 氨 、 仲丁基锂 、 sodium 、 ferric nitrate 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 7.0h， 生成 1-benzyl-2-isopropylidene-3-methylaziridine
  参考文献：
  名称：

  Generation and electrophilic substitution reactions of 3-lithio-2-methyleneaziridines

  摘要：

  2-Methyleneaziridinyl anions can be produced by selective deprotonation of the parent aziridine at C-3 using sec-BuLi/TMEDA. Subsequent reaction with a wide variety of electrophiles including MeI, ICH2CH2CH2CH2Cl, PhCH2Br, allyl bromide, Me3SiCl, Bu3SnCl, PhCHO and Ph2CO provides the corresponding C-3 substituted derivatives in moderate to good yields (43-91%). In the case of homochiral methyleneaziridines bearing an (S)-alpha-methylbenzyl group on nitrogen, high levels of diastereocontrol (up to 90%de) can be achieved in this lithiation/alkylation sequence. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.083

文献信息

• Generation and electrophilic substitution reactions of 3-lithio-2-methyleneaziridines
  作者：Cyril Montagne、Natacha Prévost、Jason J. Shiers、Gildas Prié、Sabitur Rahman、Jerome F. Hayes、Michael Shipman

  DOI：10.1016/j.tet.2006.06.083

  日期：2006.9

  2-Methyleneaziridinyl anions can be produced by selective deprotonation of the parent aziridine at C-3 using sec-BuLi/TMEDA. Subsequent reaction with a wide variety of electrophiles including MeI, ICH2CH2CH2CH2Cl, PhCH2Br, allyl bromide, Me3SiCl, Bu3SnCl, PhCHO and Ph2CO provides the corresponding C-3 substituted derivatives in moderate to good yields (43-91%). In the case of homochiral methyleneaziridines bearing an (S)-alpha-methylbenzyl group on nitrogen, high levels of diastereocontrol (up to 90%de) can be achieved in this lithiation/alkylation sequence. (c) 2006 Elsevier Ltd. All rights reserved.