1,3-bis(isopropylimino)isoindoline | 104830-26-4

• 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(isopropylimino)isoindoline
• 英文别名: 1,3-bis(isopropylimino)isoindole；1H-Isoindol-3-amine, N-(1-methylethyl)-1-[(1-methylethyl)imino]-；1-N,3-N-di(propan-2-yl)isoindole-1,3-diimine
• CAS: 104830-26-4
• 化学式: C₁₄H₁₉N₃
• 分子量: 229.325
• InChiKey: KQLKMLZRRHBJGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 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

• 作为反应物：
  描述：

  tris(bis(trimethylsilyl)amido)ytterbium(III) 、 1,3-bis(isopropylimino)isoindoline 以 四氢呋喃 为溶剂， 以91.1%的产率得到ytterbium tris[1,3-bis(isopropylimino)isoindolinate]
  参考文献：
  名称：

  1,3-Bis(alkylimino)isoindolinates of rare earth metals: Synthesis, molecular structure and photoluminescence

  摘要：

  The rare earth metal isoindolinates Ln((i)PrL)(3) (Ln = Sc (1), Y (2), Eu (3), Dy (4), Yb (5); (i)PrL= 1,3-bis(isopropylimino)isoindolinate anion) and [(MeL)Ce](2)(mu-Mel)(4) (6) (MeL = 1,3-bis(methylimino)isoindolinate anion) were synthesized by reactions of the amides Ln[N(SiMe(3))(2)](3) with 1,3-bis(isopropylimino)isoindoline ((i)PrLH) or 1,3-bis(methylimino)isoindoline (MeLH), respectively. The X-ray diffraction study revealed that in monomeric molecules of the isopropyl-substituted compounds 2 and 4 the cations Ln(3+) are eta(2)-coordinated by three isoindolinate ligands. The methyl-substituted 6 exists in a crystal as a dinner containing two terminal eta(2)-coordinated ligands and four bridging isoindolinate ligands two of which are bonded to Ce atoms in eta(3) fashion (eta:eta:eta-N,N,N) but two others in eta(4) manner (eta:eta(2):eta-N,N,N). All the obtained complexes in solutions exhibited ligand-centered photoluminescence, the spectra of which consist of one broadened band with a maximum at 400-450 nm. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2009.05.020
• 作为产物：
  描述：

  1,3-二亚胺基异吲哚啉 、 异丙胺 以 叔丁醇 为溶剂， 反应 16.0h， 以68%的产率得到1,3-bis(isopropylimino)isoindoline
  参考文献：
  名称：

  Design, synthesis, and biological activity of diiminoisoindolines as complement component 3a antagonists

  摘要：

  The failure to fully regulate the inflammation response has been linked to diseases such as rheumatoid arthritis, septic shock syndrome, and asthma. The human complement system initiates and regulates the inflammation response through a cascade of regulatory factors, Complement Component 3a (C3a) is an essential regulatory factor and inhibiting its binding to a C3a receptor will diminish the inflammation response by disrupting the cascade. We report the design, synthesis, in vitro and in vivo activity of diiminoisoindolines as C3a antagonists. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00522-4

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。
• Design, synthesis, and biological activity of diiminoisoindolines as complement component 3a antagonists
  作者：Eugene B. Grant、Deodialsingh Guiadeen、Monica Singer、Dennis Argentieri、Dennis J. Hlasta、Michael Wachter

  DOI：10.1016/s0960-894x(01)00522-4

  日期：2001.11

  The failure to fully regulate the inflammation response has been linked to diseases such as rheumatoid arthritis, septic shock syndrome, and asthma. The human complement system initiates and regulates the inflammation response through a cascade of regulatory factors, Complement Component 3a (C3a) is an essential regulatory factor and inhibiting its binding to a C3a receptor will diminish the inflammation response by disrupting the cascade. We report the design, synthesis, in vitro and in vivo activity of diiminoisoindolines as C3a antagonists. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 1,3-Bis(alkylimino)isoindolinates of rare earth metals: Synthesis, molecular structure and photoluminescence
  作者：Alexander A. Maleev、Tatyana V. Balashova、Georgy K. Fukin、Marina A. Katkova、Mikhail A. Lopatin、Mikhail N. Bochkarev

  DOI：10.1016/j.poly.2009.05.020

  日期：2010.1

  The rare earth metal isoindolinates Ln((i)PrL)(3) (Ln = Sc (1), Y (2), Eu (3), Dy (4), Yb (5); (i)PrL= 1,3-bis(isopropylimino)isoindolinate anion) and [(MeL)Ce](2)(mu-Mel)(4) (6) (MeL = 1,3-bis(methylimino)isoindolinate anion) were synthesized by reactions of the amides Ln[N(SiMe(3))(2)](3) with 1,3-bis(isopropylimino)isoindoline ((i)PrLH) or 1,3-bis(methylimino)isoindoline (MeLH), respectively. The X-ray diffraction study revealed that in monomeric molecules of the isopropyl-substituted compounds 2 and 4 the cations Ln(3+) are eta(2)-coordinated by three isoindolinate ligands. The methyl-substituted 6 exists in a crystal as a dinner containing two terminal eta(2)-coordinated ligands and four bridging isoindolinate ligands two of which are bonded to Ce atoms in eta(3) fashion (eta:eta:eta-N,N,N) but two others in eta(4) manner (eta:eta(2):eta-N,N,N). All the obtained complexes in solutions exhibited ligand-centered photoluminescence, the spectra of which consist of one broadened band with a maximum at 400-450 nm. (C) 2009 Elsevier Ltd. All rights reserved.