N-(2-methylbenzylidene)butan-1-amine | 152126-84-6

• 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: N-(2-methylbenzylidene)butan-1-amine
• 英文别名: N-butyl-1-(2-methylphenyl)methanimine
• CAS: 152126-84-6
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: AMUSQMLXZMVKMC-UHFFFAOYSA-N

物化性质

• 沸点：
  266.8±19.0 °C(Predicted)
• 密度：
  0.87±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-methylbenzylidene)butan-1-amine 在 氢氧化钾 、 sodium hydroxide 、 氯化亚砜 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 反应 58.0h， 生成 4-(4-fluoro-phenyl)-5-formyl-1-isopropyl-3-o-tolyl-1H-pyrrole-2-carboxylic acid phenylamide
  参考文献：
  名称：

  Design and synthesis of novel, conformationally restricted HMG-CoA reductase inhibitors

  摘要：

  Using structure-based design, a novel series of conformationally restricted, pyrrole-based inhibitors of HMG-CoA reductase were discovered. Leading analogs demonstrated potent inhibition of cholesterol synthesis in both in vitro and in vivo models and may be useful for the treatment of hypercholesterolemia and related lipid disorders. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.097
• 作为产物：
  描述：

  正丁胺 、 2-甲基苯甲醛 在 zirconium(IV) tetraisopropoxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 N-(2-methylbenzylidene)butan-1-amine
  参考文献：
  名称：

  首个高效的两步/一锅异丙醇锆（IV）介导的羰基化合物还原胺化反应

  摘要：

  据报道，通过异丙醇锆（IV）介导的醛和酮的还原胺化反应，可以有效地合成各种伯胺和仲胺。使用了一系列不同的醛，酮和胺，以中等到极好的收率得到了预期的氨基产物。已通过形成瞬时亚胺物种和使用（R）-苯基乙胺作为手性诱导剂的非对映选择性形式推测了该反应的机理原理，从而以中等至优异的收率获得了预期的产物，非对映选择性高达100％。

  DOI：

  10.2174/1570180812666141215215120

文献信息

• Intramolecular C(sp³)N Coupling by Oxidation of Benzylic C,N-Dianions
  作者：Jenna L. Jeffrey、Emily S. Bartlett、Richmond Sarpong

  DOI：10.1002/anie.201209591

  日期：2013.2.18

  azacycles is reported. This reaction proceeds through the oxidation of benzylic C,N‐dianions with iodine and builds on an earlier discovery during the synthesis of the natural product lyconadin A. The current study employs conformationally unbiased substrates with less acidic CH bonds and less reactive nitrogen nucleophiles. ZnCl2 was identified as an important additive.

  多么一对！据报道，分子内 C(sp 3 )  N 偶联可提供氮杂环。该反应通过用碘氧化苄型 C,N-二价阴离子进行，并建立在合成天然产物 lyconadin A 期间的早期发现的基础上。目前的研究使用具有较低酸性 C  H 键和较低活性氮亲核试剂的构象无偏底物. ZnCl 2被确定为一种重要的添加剂。
• Au nanoparticle-immobilized l-cysteine-paired porous ionic copolymer as an efficient catalyst for additive-free oxidative coupling of alcohols and amines
  作者：Shengyu Du、Chenjun Zhang、Yuchen Jiang、Pingping Jiang、Yan Leng

  DOI：10.1016/j.catcom.2019.105746

  日期：2019.9

  Herein, an l-cysteine-paired ionic copolymer (DVB-[MimLcy]n) with mesoporosity was prepared by free radical copolymerization of divinylbenzene (DVB) and imidazolium ionic liquids (ILs), followed by anion-exchange with l-cysteine. Because of the rich functional groups of NH2, SH, and COO– and the porous framework, the DVB-[MimLcy]3 was revealed to be an ideal stabilizer for metal nanoparticles (NPs)

  本文中，升-半胱氨酸配对离子共聚物（DVB-[MimLcy] Ñ）与中孔是由二乙烯基苯（DVB）和咪唑鎓的离子液体（离子液体）的自由基共聚，随后用阴离子交换制备的升-半胱氨酸。由于富官能团NH 2，SH，和COO -和多孔框架中，DVB-[MimLcy] 3显露是用于金属纳米颗粒（NP）的理想的稳定剂。固定在DVB- [MimLcy] 3（Au a / DVB- [MimLcy] 3上的高度均匀分散的小Au NP（2-3 nm））可以通过广泛的醇类和有机胺的偶联，作为亚胺的无添加剂合成的高效多相催化剂，并且可以轻松回收并稳定重复使用数次。
• Synthesis of Secondary Aldimines from the Hydrogenative Cross-Coupling of Nitriles and Amines over Al₂O₃-Supported Ni Catalysts
  作者：Peng Zhou、Liang Jiang、Shuguo Wang、Xun Hu、Hongming Wang、Ziliang Yuan、Zehui Zhang

  DOI：10.1021/acscatal.9b01597

  日期：2019.9.6

  A heterogeneous Ni catalyst was discovered to be active in the synthesis of secondary cross-imines via hydrogenative coupling of nitriles and amines. The mesoporous Al2O3-supported Ni nanoparticles (abbreviated as Ni/m-Al2O3-600, where 600 represents the reduction temperature) were active in hydrogenative coupling of nitriles and amines reaction at 80 °C and 1 bar H2, affording corresponding cross-imines

  发现一种非均质的Ni催化剂可通过腈和胺的加氢偶合而在次级交叉亚胺的合成中发挥作用。在80°C和1 bar H 2下，介孔的Al 2 O 3负载的Ni纳米颗粒（缩写为Ni / m-Al 2 O 3 -600，其中600表示还原温度）在腈和胺的氢化反应中具有活性。，提供相应的交叉亚胺，产率在64.1–98.1％的范围内。密度泛函理论计算表明，苯甲腈（PhCN）氢化为苄胺（PhCH 2 NH 2）的活化能比PhCN和RNH 2的氢化交叉偶联的活化能高。Ni / m-Al 2 O 3 -600催化剂上的反应，表明后者反应更有利。理论计算与我们的实验结果非常吻合。
• Steric and Electronic Effects in Capsule-Confined Green Fluorescent Protein Chromophores
  作者：Anthony Baldridge、Shampa R. Samanta、Nithyanandhan Jayaraj、V. Ramamurthy、Laren M. Tolbert

  DOI：10.1021/ja1094606

  日期：2011.2.2

  The turn-on of emission in fluorescent protein chromophores sequestered in an "octaacid" capsule is controlled by stereoelectronic effects described by a linear free energy relationship. The stereochemical effects are governed by both the positions and volumes of the aryl substituents, while the electronic effects, including ortho effects, can be treated with Hammett sigma parameters. The use of substituent volumes rather than A values reflects packing of the molecule within the confines of the capsule.
• Activation of Fluorescent Protein Chromophores by Encapsulation
  作者：Anthony Baldridge、Shampa R. Samanta、Nithyanandhan Jayaraj、V. Ramamurthy、Laren M. Tolbert

  DOI：10.1021/ja908870k

  日期：2010.2.10

  Chromophores related to fluorescent proteins, when sequestered into the "octaacid" capsule, recover their fluorescence, The fluorescence recovery is related to the inhibition of torsional motions within the cavity, implicating the single-bond torsion as an important contributor to internal conversion within this important class of chromophores.