2-(2,3,4,5-tetramethylcyclopent-2-en-1-ylidene)ethan-1-amine | 308116-90-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 2-(2,3,4,5-tetramethylcyclopent-2-en-1-ylidene)ethan-1-amine
• CAS: 308116-90-7
• 化学式: C₁₁H₁₉N
• 分子量: 165.279
• InChiKey: OXRZXXXAZCKJFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  26.02
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  盐酸 、 氯化铱(III) 水合物 、 2-(2,3,4,5-tetramethylcyclopent-2-en-1-ylidene)ethan-1-amine 以 乙醇 为溶剂， 以21%的产率得到[(η5-Me4C5(CH2)2NH3)IrCl2]Cl2
  参考文献：
  名称：

  Side chain functionalized η5-tetramethyl cyclopentadienyl complexes of Rh and Ir with a pendant primary amine group

  摘要：

  Conversion of 2-(2,3,4,5-tetramethylcyclopentadien) ethylamine tautomere C5Me4H2(CHCH2)NH2 (1) with MCl3 center dot n H2O (M = Rh, Ir) under acidic conditions gives the respective mu-chloro-bridged chelates [(eta(5)-Me4Cp(CH2)(2)NH3)RhCl2](2)Cl-2 (2) and [(eta(5)-Me4Cp(CH2)(2)NH3)IrCl2](2)Cl-2 (3). The dimeric complexes are received as ammonium salts and thus display good solubility in strong donor solvents such as water and DMSO. Addition of triphenyl phosphine converts Rh-dimer 2 into the mononuclear phosphine complex 4. Under basic conditions, no intramolecular coordination of the pendant NH2 is observed and thus the primary amino group of 4 reacts selectively with succinic anhydride by formation of a peptide bond. Hence, the electrophilic metal center and the latent nucleophilic nitrogen, which represent complementary functionalities, can be addressed separately under the appropriate reaction conditions. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.01.056

文献信息

• Easy preparation of Cp*-functionalized N-heterocyclic carbenes and their coordination to rhodium and iridium
  作者：André Pontes da Costa、Mercedes Sanaú、Eduardo Peris、Beatriz Royo

  DOI：10.1039/b901195a

  日期：——

  A simple high-yielding method for the preparation of a tetramethylcyclopentadienyl-NHC ligand is described. This ligand has been successfully coordinated to Rh and Ir. A related Cp*-NHC ligand with a -CH(2)CMePh- linker between the Cp* and the NHC is also described, together with its coordination to Rh and Ir. This latter ligand, affords the orthocyclometallation of the phenyl ring yielding a constrained

  描述了用于制备四甲基环戊二烯基-NHC配体的简单的高产率方法。该配体已成功配位至Rh和Ir。还描述了在Cp *和NHC之间带有-CH（2）CMePh-接头的相关Cp * -NHC配体，及其与Rh和Ir的配位。后一种配体提供苯环的邻环金属化，从而产生约束结构，其中配体是三齿的。所有配合物均已被充分表征，并描述了其晶体结构。还报道了关于仲醇的β-烷基化和苯胺与伯醇的N-烷基化的初步催化结果。