1H-pyrrol-2-ylmethylbenzylamine | 95116-31-7

• 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: 1H-pyrrol-2-ylmethylbenzylamine
• 英文别名: 1H-Pyrrole-2-methanamine, N-(phenylmethyl)-；1-phenyl-N-(1H-pyrrol-2-ylmethyl)methanamine
• CAS: 95116-31-7
• 化学式: C₁₂H₁₄N₂
• mdl: MFCD16661956
• 分子量: 186.257
• InChiKey: YOGRUDYQEJQNLR-UHFFFAOYSA-N

物化性质

• 熔点：
  95-98 °C(Solv: toluene (108-88-3); cyclohexane (110-82-7))
• 沸点：
  327.3±22.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1H-pyrrol-2-ylmethylbenzylamine 在 吡啶 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 29.0h， 生成 [(E)-4-[benzyl(1H-pyrrol-2-ylmethyl)amino]but-2-enyl] methyl carbonate
  参考文献：
  名称：

  Highly Enantioselective Synthesis of Tetrahydro-β-Carbolines and Tetrahydro-γ-Carbolines Via Pd-Catalyzed Intramolecular Allylic Alkylation

  摘要：

  A novel Pd-catalyzed intramolecular allylic alkylation of indoles allows THBCs and THGCs to be effectively synthesized in high yields and excellent enantiomeric excesses (ee up to 97%).

  DOI：

  10.1021/ja054109o
• 作为产物：
  描述：

  N-benzyl-N-(1H-pyrrolylmethylidene)amine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以71.3%的产率得到1H-pyrrol-2-ylmethylbenzylamine
  参考文献：
  名称：

  吡啶-胺-吡咯配体复合 [RhI(cod)]+ 和 [IrI(cod)]+ 的多样性

  摘要：

  [RhI(cod)]+ 和 [IrI(cod)]+ 通过新的吡啶-胺-吡咯配体 Py–CH2–N(R)–CH2–Pyr–H (HLR; R = H, Bzl, Bu ) 和相应的吡啶-胺-吡咯配体 [Py-CH2-N(R)-CH2-Pyr]- (LR-; R = H, Bzl, Bu, CH2Py) 已被研究。中性配体 HLR (R = H, Bu, Bzl) 得到 [(HLR)MI(cod)]+ (M = Rh, Ir)，其中 HLR 通过吡啶氮 (NPy) 和胺氮充当双齿配体(NRamine)。[(HLH)MI(cod)]PF6 (M = Rh: [1]PF6 和 M = Ir: [2]PF6) 的晶体结构已经确定。[(HLR)MI(cod)]+ (M = Rh, Ir; R = H, Bzl, Bu) 的去质子化产生中性复合物 [(LR)MI(cod)] (M = Rh, Ir)单阴离子配体

  DOI：

  10.1002/(sici)1099-0682(199909)1999:9<1581::aid-ejic1581>3.0.co;2-1

文献信息

• Pyrrole-based metallo-macrocycles and cryptands
  作者：Paul D. Beer、Andrew G. Cheetham、Michael G. B. Drew、O. Danny Fox、Elizabeth J. Hayes、Toby D. Rolls

  DOI：10.1039/b210099a

  日期：2003.2.11

  is reported. These ligands self-assemble with zinc(II), nickel(II) and copper(II) to afford neutral, dinuclear metallomacrocycles and trinuclear metallocryptands. The assembled metallo compounds have been characterised by a range of techniques, including 1H NMR, UV-vis spectroscopy, elemental analysis, mass spectrometry and X-ray crystallography. Some preliminary anion binding studies have also been

  二硫代氨基甲酸酯的合成 配体基于吡咯框架的报道。这些配体与锌（II），镍（II）和铜（II）自组装，以提供中性，双核金属大环和三核金属链烷烃。组装的金属化合物已通过多种技术进行了表征，包括1 H NMR， 紫外线可见 光谱学， 元素分析， 质谱 和 X射线晶体学。还进行了一些初步的阴离子结合研究，使用电子光谱学和电化学。镍大环 对乙酸盐有一定的亲和力，而铜穴状对乙酸盐有亲和力 苯甲酸酯阴离子。穴状铜还表现出对一系列阴离子的显着电化学反应。
• Diversity in Complexation of [RhI(cod)]+ and [IrI(cod)]+ by Pyridine-Amine-Pyrrole Ligands
  作者：Bas de Bruin、Reinout J. N. A. M. Kicken、Nicolaas F. A. Suos、Maurice P. J. Donners、Carolien J. den Reijer、Albertus J. Sandee、René de Gelder、Jan M. M. Smits、Anton W. Gal、Anton L. Spek

  DOI：10.1002/(sici)1099-0682(199909)1999:9<1581::aid-ejic1581>3.0.co;2-1

  日期：1999.9

  = Ir. The neutral complexes [Py–CH2–N(R)–CH2–Pyr}MI(cod)] (M = Rh, Ir) cannot be oxidised selectively with H2O2. This is in marked contrast to the previously observed selective oxidation of the corresponding cationic complexes [Py–CH2–N(R)–CH2–Py}RhI(cod)]+. Rhodium complex 5 is an active catalyst for the stereoregular polymerisation of phenylacetylene, whereas iridium complex 6 is inactive.

  [RhI(cod)]+ 和 [IrI(cod)]+ 通过新的吡啶-胺-吡咯配体 Py–CH2–N(R)–CH2–Pyr–H (HLR; R = H, Bzl, Bu ) 和相应的吡啶-胺-吡咯配体 [Py-CH2-N(R)-CH2-Pyr]- (LR-; R = H, Bzl, Bu, CH2Py) 已被研究。中性配体 HLR (R = H, Bu, Bzl) 得到 [(HLR)MI(cod)]+ (M = Rh, Ir)，其中 HLR 通过吡啶氮 (NPy) 和胺氮充当双齿配体(NRamine)。[(HLH)MI(cod)]PF6 (M = Rh: [1]PF6 和 M = Ir: [2]PF6) 的晶体结构已经确定。[(HLR)MI(cod)]+ (M = Rh, Ir; R = H, Bzl, Bu) 的去质子化产生中性复合物 [(LR)MI(cod)] (M = Rh, Ir)单阴离子配体
• Enantioselective Functionalization of Indoles and Pyrroles via an in Situ-Formed Spiro Intermediate
  作者：Chun-Xiang Zhuo、Qing-Feng Wu、Qiang Zhao、Qing-Long Xu、Shu-Li You

  DOI：10.1021/ja403535a

  日期：2013.6.5

  Herein we report a highly enantioselective synthesis of polycyclic indoles and pyrroles with up to 99% ee by an iridium catalyst system consisting of a commercially available iridium precursor and a readily accessible ligand. Investigation of the reaction mechanism led to the discovery of an unprecedented dearomatized spiro intermediate and its in situ migration phenomenon. The new reaction mode features

  在此，我们报告了通过由市售的铱前体和易于获得的配体组成的铱催化剂系统，高度对映选择性合成多环吲哚和吡咯的 ee 高达 99%。对反应机理的研究导致发现了一种前所未有的脱芳构化螺环中间体及其原位迁移现象。新的反应模式的特点是将取代基从吲哚 C-3 位置切换到 C-2 位置（在吡咯的情况下从 C-2 位置切换到 C-3 位置）而不损失对映体纯度，提供了设计对映纯多环吲哚和吡咯的不对称结构的新概念。
• 10.1039/d4cc00959b
  作者：Kumar, Dharmendra、Unnikrishnan, Urmila、Kuram, Malleswara Rao

  DOI：10.1039/d4cc00959b

  日期：——

  challenge. A simple copper-catalyzed strategy for synthesizing C-substituted piperazinones is described, employing easily accessible diazo compounds and 1,2-diamines. The reaction proceeded via chemo-selective carbene insertion at the comparatively less nucleophilic amine, followed by instantaneous cyclization. The protocol was further extended to access NH-free piperazinone, and the synthesis of a Mianserin

  将不对称二胺化学选择性 N-H 插入卡宾是一个长期存在的挑战。描述了一种简单的铜催化合成C-取代哌嗪酮的策略，使用容易获得的重氮化合物和 1,2-二胺。该反应通过化学选择性卡宾插入亲核性相对较低的胺进行，然后瞬时环化。该方案进一步扩展以获取不含 NH 的哌嗪酮，并合成米安色林衍生物。
• New Pyrrole Inhibitors of Monoamine Oxidase:  Synthesis, Biological Evaluation, and Structural Determinants of MAO-A and MAO-B Selectivity
  作者：Giuseppe La Regina、Romano Silvestri、Marino Artico、Antonio Lavecchia、Ettore Novellino、Olivia Befani、Paola Turini、Enzo Agostinelli

  DOI：10.1021/jm060882y

  日期：2007.3.1

  A series of new pyrrole derivatives have been synthesized and evaluated for their monoamine oxidase (MAO) A and B inhibitory activity and selectivity. N-Methyl,N-(benzyl),N-(pyrrol-2-ylmethyl)amine (7) and N-(2-benzyl),N-(1-methylpyrrol-2-ylmethyl)amine (18) were the most selective MAO-B (7, SI = 0.0057) and MAO-A (18, SI = 12500) inhibitors, respectively. Docking and molecular dynamics simulations gave structural insights into the MAO-A and MAO-B selectivity. Compound 18 forms an H-bond with Gln215 through its protonated amino group into the MAO-A binding site. This H-bond is absent in the 7/MAO-A complex. In contrast, compound 7 places its phenyl ring into an aromatic cage of the MAO-B binding pocket, where it forms charge-transfer interactions. The slightly different binding pose of 18 into the MAO-B active site seems to be forced by a bulkier Tyr residue, which replaces a smaller Ile residue present in MAO-A.