N-(4-chlorobenzyl)-N-isopropylpropan-2-amine | 359445-35-5

• 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-(4-chlorobenzyl)-N-isopropylpropan-2-amine
• 英文别名: N-[(4-chlorophenyl)methyl]-N-propan-2-ylpropan-2-amine
• CAS: 359445-35-5
• 化学式: C₁₃H₂₀ClN
• 分子量: 225.762
• InChiKey: SEZANFJHQLQHGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(4-chlorobenzyl)-N-isopropylpropan-2-amine 在 碘 、 sodium carbonate 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以84%的产率得到N-(4-氯苄基)异丙基胺
  参考文献：
  名称：

  Transformation of N,N-diisopropylarylmethylamines into N-isopropylarylmethylamines with molecular iodine

  摘要：

  N,N-Diisopropylarylmethylamines were smoothly converted into the corresponding N-isopropylaryl-methylamines by the reaction with molecular iodine in the presence of Na2CO3 in chloroform at 60 degrees C. Other related tertiary amines were also transformed into the corresponding secondary amines by the reaction with molecular iodine under the same reaction conditions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.044
• 作为产物：
  描述：

  4-氯-N,N-二异丙基苯甲酰胺 在 三氟甲磺酸酐 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 0.5h， 以91%的产率得到N-(4-chlorobenzyl)-N-isopropylpropan-2-amine
  参考文献：
  名称：

  Amide Activation by Tf2O: Reduction of Amides to Amines by NaBH4 under Mild Conditions

  摘要：

  报道了一种快速且实用的酰胺还原为胺的方法。该方法包括使用Tf2O对酰胺进行活化，然后在室温下用四氢呋喃中的硼氢化钠进行还原。各种酰胺/内酰胺都能以良好到优异的产率生成相应的胺，即使是对立体的酰胺和二级酰胺也如此。该方法还具有其他优点，如对TBDPS基团的耐受性、反应时间短、操作简便以及纯化过程简单。

  DOI：

  10.1055/s-0030-1258111

文献信息

• Nickel-Catalyzed Alkylarylation of Activated Alkenes with Benzyl-amines via C−N Bond Activation
  作者：Hui Yu、Bin Hu、Hanmin Huang

  DOI：10.1002/chem.201800543

  日期：2018.5.17

  A nickel‐catalyzed alkylarylation of active alkenes with tertiary benzylamines was achieved by charge‐transfer‐complex promoted C−N bond activation. The reaction proceeded through initial Ni‐catalyzed C−N bond activation, followed by sequential radical addition, redox and proton abstraction with cleaved amine moiety in the absence of oxidant, and provides an efficient method to prepare various alkyl‐substituted

  通过电荷转移络合物促进的C-N键活化，实现了镍与叔苄基胺催化的活性烯烃烷基芳基化反应。该反应通过最初的Ni催化的C-N键活化而进行，然后在不存在氧化剂的情况下依次进行自由基加成，氧化还原和带有裂解的胺部分的质子提取，为制备各种烷基取代的羟吲哚和二氢喹啉酮提供了一种有效的方法。产量。
• Charge-Transfer Complex Promoted C–N Bond Activation for Ni-Catalyzed Carbonylation
  作者：Hui Yu、Bao Gao、Bin Hu、Hanmin Huang

  DOI：10.1021/acs.orglett.7b01488

  日期：2017.7.7

  A new strategy was developed for activation of C–N bond via formation of an amine–I2 charge-transfer complex, which facilitates the inert C–N bond activation via oxidative addition with Ni(0). This strategy has been successfully applied in the Ni-catalyzed carbonylation of benzylamines via direct insertion of CO into the C–N bond, which provided a straightforward and rapid approach to arylacetamides

  通过形成胺-I 2电荷转移络合物，开发了一种激活C–N键的新策略，该方法通过与Ni（0）的氧化加成促进了惰性C–N键的激活。通过将CO直接插入C–N键中，该策略已成功地应用于Ni催化的苄胺的羰基化反应，这为在催化量的I 2和Ni催化剂存在下芳基乙酰胺的制备提供了一种直接而快速的方法。机理研究表明，通过氧化加成产生的苄基自由基参与了本反应。
• Amide Activation by Tf2O: Reduction of Amides to Amines by NaBH4 under Mild Conditions
  作者：Pei-Qiang Huang、Shao-Hua Xiang、Jian Xu、Hong-Qiu Yuan

  DOI：10.1055/s-0030-1258111

  日期：2010.7

  An expeditious and practical method for the reduction of amides to amines is reported. The method is consisted of activation of amides with Tf2O followed by reduction with sodium borohydride in THF at room temperature. Various amides/lactams gave the corresponding amines in good to excellent yields, even with hindered amides and secondary amides. This method also presents other advantages such as TBDPS-group tolerance, short reaction time, simple workup and purification procedure.

  报道了一种快速且实用的酰胺还原为胺的方法。该方法包括使用Tf2O对酰胺进行活化，然后在室温下用四氢呋喃中的硼氢化钠进行还原。各种酰胺/内酰胺都能以良好到优异的产率生成相应的胺，即使是对立体的酰胺和二级酰胺也如此。该方法还具有其他优点，如对TBDPS基团的耐受性、反应时间短、操作简便以及纯化过程简单。
• Nickel-Catalyzed Benzylation of Aryl Alkenes with Benzylamines via C–N Bond Activation
  作者：Hui Yu、Bin Hu、Hanmin Huang

  DOI：10.1021/acs.joc.8b02279

  日期：2018.11.16

  example of nickel-catalyzed Heck-type benzylation of aryl olefins with various benzylamines as benzyl electrophiles, and the benzylic C–N bond cleavage was efficiently promoted by the amine–I2 charge transfer complex (CT complex). The combination of low-cost NiCl2 and I2 has been found to facilitate Heck reaction of tertiary benzylamines and alkenes into various benzyl-substituted alkenes in good to

  我们开发了第一个实例，用各种苄胺作为苄基亲电子体，镍催化芳基烯烃的Heck型苄基化，而胺I 2电荷转移络合物（CT络合物）有效地促进了苄基C–N键的裂解。已经发现低成本NiCl 2和I 2的组合以良好至优异的产率促进叔苄胺和烯烃的Heck反应成各种苄基取代的烯烃。提出了这种非常规的Heck反应，首先通过与Ni（0）的C–N键的氧化加成反应形成苄基，然后通过自由基加成被芳基烯烃捕获，然后进行单电子转移氧化还原和质子提取没有氧化剂和外部碱。
• Transformation of N,N-diisopropylarylmethylamines into N-isopropylarylmethylamines with molecular iodine
  作者：Masatoshi Ezawa、Katsuhiko Moriyama、Hideo Togo

  DOI：10.1016/j.tetlet.2015.10.044

  日期：2015.12

  N,N-Diisopropylarylmethylamines were smoothly converted into the corresponding N-isopropylaryl-methylamines by the reaction with molecular iodine in the presence of Na2CO3 in chloroform at 60 degrees C. Other related tertiary amines were also transformed into the corresponding secondary amines by the reaction with molecular iodine under the same reaction conditions. (C) 2015 Elsevier Ltd. All rights reserved.