1,3-bis-n-propyliminoisoindoline | 93423-55-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1,3-bis-n-propyliminoisoindoline
• 英文别名: 1,3-bis(propylimino)isoindoline；Bis(propylimino)isoindoline；1-N,3-N-dipropylisoindole-1,3-diimine
• CAS: 93423-55-3
• 化学式: C₁₄H₁₉N₃
• 分子量: 229.325
• InChiKey: KVNABIQLCPEFFU-UHFFFAOYSA-N

物化性质

• 沸点：
  361.5±25.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  36.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2-二氰基苯 在 氨 、 sodium 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 28.0h， 生成 1,3-bis-n-propyliminoisoindoline
  参考文献：
  名称：

  The syntheses and structures of bis(alkylimino)isoindolines

  摘要：

  In this Letter, we present a synthetic and structural study into bis-imino substituted diiminoisoindolines, which can be synthesized either via CaCl2 mediated reaction of phthalonitrile with primary amines, or via direct reaction of these amines with unsubstituted diiminoisoindoline. The preferred synthesis does depend on the methodology, and in two cases singly substituted adducts were formed. The single crystal X-ray structures show that, with the exception of the bis-naphthyl compound, the anti conformation is preferred, and that the ionizable hydrogen atom resides on an exocyclic nitrogen rather than the central isoindoline nitrogen atom. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.134

文献信息

• SYNTHESIS OF 1,3-DIIMINOISOINDOLINES FROM 2-CYANOBENZALDEHYDE. REACTION OF<i>N</i>-(2-CYANOBENZYLIDENE)ANILINES WITH ELEMENTAL SULFUR IN LIQUID AMMONIA AND AMINES
  作者：Ryu Sato、Mikiya Nakayama、Yoshiki Yuzawa、Takehiko Goto、Minoru Saito

  DOI：10.1246/cl.1985.1887

  日期：1985.12.5

  Various 1,3-diimonoisoindolines were obtained by treating N-(2-cyanobenzylidene)anilines with elemental sulfur in liquid ammonia and amines. A novel route to isoindoline from 2-cyanobenzaldehyde was developed.

  通过在液氨和胺中用元素硫处理 N-（2-氰基亚苄基）苯胺，获得了各种 1,3-二亚甲基异二氢吲哚。开发了一种从 2-氰基苯甲醛制备异二氢吲哚的新途径。
• Lanthanide triiodide-catalyzed amination of phthalonitrile. The structure of 1-isopropylamino-3-(isopropylimino)isoindole
  作者：M. N. Bochkarev、T. V. Balashova、A. A. Maleev、I. I. Pestova、G. K. Fukin、E. V. Baranov、Yu. A. Kurskii

  DOI：10.1007/s11172-008-0293-3

  日期：2008.10

  (Ln = Gd or Nd) afford 1,3-bis(alkylimino)isoindolines (Alk = Me (1), Prn (2), or Pri (3), respectively). Under analogous conditions, 2-aminopyridine gives 1,3-bis(2-pyridylimino)isoindoline (4). The X-ray diffraction study of compound 3 showed that, in the crystalline state, this compound exists as the isomer, 1-isopropylamino-3-(isopropylimino)isoindole.

  在催化量的 LnI3（Ln = Nd 或 Dy）或 LnI3(THF)3（Ln = Gd 或 Nd）存在下，邻苯二甲腈与 MeNH2、PrnNH2 和 PriNH2 的反应得到 1,3-双（烷基亚氨基）异二氢吲哚（ Alk = Me (1)、Prn (2) 或 Pri (3)。在类似条件下，2-氨基吡啶生成 1,3-双（2-吡啶亚氨基）异二氢吲哚 (4)。化合物 3 的 X 射线衍射研究表明，在结晶状态下，该化合物以异构体 1-异丙基氨基-3-（异丙基亚氨基）异吲哚存在。
• ELEMENTAL SULFUR-CATALYZED SYNTHESIS OF<i>N</i>,<i>N</i>′-DISUBSTITUTED 1,3-DIIMINOISOINDOLINES FROM PHTHALONITRILE WITH AMMONIA AND AMINES
  作者：Ryu Sato、Toshihide Senzaki、Yoshihiro Shikazaki、Takehiko Goto、Minoru Saito

  DOI：10.1246/cl.1984.1423

  日期：1984.8.5

  Various N,N′-disubstituted 1,3-diiminoisoindolines were synthesized by.the elemental sulfur-catalyzed reaction of phthalonitrile with ammonia and some primary amines in excellent yields. Several functionalized isoindolines were also obtained in high yields.

  通过元素硫催化邻苯二腈与氨和一些伯胺的反应，合成了各种 N,N′-二取代的 1,3-二亚氨基异吲哚啉，产量极高。此外，还以高产率获得了几种官能化的异吲哚胺。
• SATO, RYU;SENZAKI, TOSHIHIDE;SHIKAZIKI, YOSHIHIRO;GOTO, TAKEHIKO;SAITO, M+, CHEM. LETT., 1984, N 8, 1423-1426
  作者：SATO, RYU、SENZAKI, TOSHIHIDE、SHIKAZIKI, YOSHIHIRO、GOTO, TAKEHIKO、SAITO, M+

  DOI：——

  日期：——
• The syntheses and structures of bis(alkylimino)isoindolines
  作者：Ingrid-Suzy Tamgho、James T. Engle、Christopher J. Ziegler

  DOI：10.1016/j.tetlet.2013.08.134

  日期：2013.11

  In this Letter, we present a synthetic and structural study into bis-imino substituted diiminoisoindolines, which can be synthesized either via CaCl2 mediated reaction of phthalonitrile with primary amines, or via direct reaction of these amines with unsubstituted diiminoisoindoline. The preferred synthesis does depend on the methodology, and in two cases singly substituted adducts were formed. The single crystal X-ray structures show that, with the exception of the bis-naphthyl compound, the anti conformation is preferred, and that the ionizable hydrogen atom resides on an exocyclic nitrogen rather than the central isoindoline nitrogen atom. (C) 2013 Elsevier Ltd. All rights reserved.