N-(2-氯苄基)苯胺 | 41001-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(2-氯苄基)苯胺
• 中文别名: (2-氯苄基)-苯基-胺
• 英文名称: N-(2-chlorobenzyl)aniline
• 英文别名: N-(2-chlorobenzyl)benzenamine；N-(2-chloro-benzyl)-aniline；N-(2-Chlor-benzyl)-anilin；Phenyl-(2-chlor-benzyl)-amin；N-(o-chlorobenzyl)aniline；N-Phenyl-N-o-chlor-benzylamin；N-(2-chlorobenzyl)-N-phenylamine；N-[(2-chlorophenyl)methyl]aniline
• CAS: 41001-24-5
• 化学式: C₁₃H₁₂ClN
• mdl: MFCD03210813
• 分子量: 217.698
• InChiKey: SWKUGGDNDCPQIF-UHFFFAOYSA-N

物化性质

• 熔点：
  40 °C
• 沸点：
  337.6±17.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2921499090

反应信息

• 作为反应物：
  描述：

  N-(2-氯苄基)苯胺 在 氨 、 potassium amide 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 5,6-dihydrophenanthridine
  参考文献：
  名称：

  Benzyne cyclization route to benzo[c]phenanthridine alkaloids. Synthesis of chelerythrine, decarine, and nitidine

  摘要：

  DOI：

  10.1021/jo00243a020
• 作为产物：
  描述：

  2-氯-N-苯基苯甲酰胺 在 四氯化钛 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到N-(2-氯苄基)苯胺
  参考文献：
  名称：

  方便，通用地将酰胺还原为低价钛的胺

  摘要：

  AbstractLow‐valent titanium readily prepared in situ from TiCl4 and Mg powder in THF is found to be an active agent for the reduction of amides which were previously considered to be inert towards low‐valent titanium. The reaction proceeds under very mild conditions, and is applicable to all types of amides, primary, secondary and tertiary, to produce the corresponding amines in good to excellent yields. This new finding provides a practical, convenient and general method for the important transformation of amides to amines. A plausible reaction mechanism is proposed.magnified image

  DOI：

  10.1002/adsc.201300355

文献信息

• Direct One‐Pot Reductive N‐Alkylation of Nitroarenes by using Alcohols with Supported Gold Catalysts
  作者：Chun‐Hong Tang、Lin He、Yong‐Mei Liu、Yong Cao、He‐Yong He、Kang‐Nian Fan

  DOI：10.1002/chem.201100393

  日期：2011.6.20

  Gold standard support! The direct reductive mono‐ or di‐N‐alkylation of aromatic nitro compounds with alcohols, using a hydrogen‐borrowing strategy, was efficiently promoted by a ligand‐free titania‐supported gold catalyst system (see scheme). A variety of nitroarenes were selectively converted into the corresponding secondary or tertiary amines in good to excellent yields without any co‐catalysts

  黄金标准支持！不含氢的二氧化钛负载的金催化剂体系有效地促进了使用氢借用策略使芳香族硝基化合物与醇直接还原成单-或二-N-烷基化反应（参见方案）。在不使用任何助催化剂（例如碱和稳定配体）的情况下，可以将各种硝基芳烃以良好的优良性能选择性地转化为相应的仲胺或叔胺。
• Green synthesis and catalytic properties of palladium nanoparticles for the direct reductive amination of aldehydes and hydrogenation of unsaturated ketones
  作者：Mahmoud Nasrollahzadeh

  DOI：10.1039/c4nj01440e

  日期：——

  This paper reports on the synthesis and use of palladium nanoparticles as heterogeneous catalysts for the reductive amination of aldehydes and hydrogenation of unsaturated ketones. This method has the advantages of high yields, simple methodology and easy work up. The catalyst can be recovered and reused several times without significant loss of catalytic activity.

  本文报道了钯纳米粒子的合成及其作为非均相催化剂用于醛的还原胺化和不饱和酮加氢的应用。该方法具有收率高，方法简单，后处理容易的优点。催化剂可以回收并重复使用几次，而不会显着降低催化活性。
• A Rapid and Additive-Free Ruthenium-Catalyzed Reductive Amination of Aromatic Aldehydes
  作者：Christian Kerner、Sascha-Dominic Straub、Y. Sun、Werner R. Thiel

  DOI：10.1002/ejoc.201600515

  日期：2016.6

  2-[2-(dimethylamino)pyrimidin-4-yl]pyridine} is highly reactive in catalyzing the reductive amination of aromatic aldehydes through in situ generated imines with 2-propanol as the hydrogen source following a transfer-hydrogenation mechanism. This transformation does not require any activating additives and is applicable to a broad variety of aldehydes.

  钌配合物 [(η6-cymene)Ru(Cl)(dpmpy)]+ dpmpy = 2-[2-(二甲基氨基)pyrimidin-4-yl]pyridine} 在催化芳香醛的还原胺化时具有高活性原位生成亚胺，以 2-丙醇为氢源，遵循转移加氢机制。这种转变不需要任何活化添加剂，适用于多种醛。
• Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride
  作者：Veronica Airoldi、Oreste Piccolo、Gabriella Roda、Rebecca Appiani、Francesco Bavo、Riccardo Tassini、Stefano Paganelli、Sebastiano Arnoldi、Marco Pallavicini、Cristiano Bolchi

  DOI：10.1002/ejoc.201901614

  日期：2020.1.16

  Aldehydes and ketones were reductively aminated by a one‐pot procedure using a recyclable iron‐based Lewis catalyst, Aquivion‐Fe, to promote imine formation, and NaBH4 as reductant in cyclopentyl methyl ether and methanol. The developed protocol was successfully applied to the preparation of Cinacalcet, an important active pharmaceutical ingredient.

  使用可循环使用的铁基路​​易斯催化剂Aquivion-Fe，通过一锅法将醛和酮还原胺化，以促进亚胺的形成，并用NaBH 4作为环戊基甲基醚和甲醇中的还原剂。所开发的方案已成功应用于重要活性药物成分Cinacalcet的制备。
• Enhanced Hydride Donation Achieved Molybdenum Catalyzed Direct <i>N</i>-Alkylation of Anilines or Nitroarenes with Alcohols: From Computational Design to Experiment
  作者：Weikang Li、Ming Huang、Jiahao Liu、Yong-Liang Huang、Xiao-Bing Lan、Zongren Ye、Cunyuan Zhao、Yan Liu、Zhuofeng Ke

  DOI：10.1021/acscatal.1c02956

  日期：2021.8.20

  An example of homogeneous Mo-catalyzed direct N-alkylation of anilines or nitroarenes with alcohols is presented. The DFT aimed design suggested the easily accessible bis-NHC-Mo(0) complex features a strong hydride-donating ability, achieving effective N-alkylation of anilines or challenging nitroarenes with alcohols. The enhanced hydride-donating strategy should be useful in designing highly active

  介绍了均相 Mo 催化的苯胺或硝基芳烃与醇的直接N-烷基化的例子。DFT 目标设计表明，易于获得的双-NHC-Mo(0) 配合物具有强大的氢化物供体能力，可实现苯胺的有效N-烷基化或用醇挑战硝基芳烃。增强的氢化物捐赠策略应该有助于设计用于借氢转化的高活性系统。