N-benzyl-(1-phenyl-2-methyl-butyl)amine | 1004517-72-9

• 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-benzyl-(1-phenyl-2-methyl-butyl)amine
• 英文别名: N-benzyl-2-methyl-1-phenylbutan-1-amine
• CAS: 1004517-72-9
• 化学式: C₁₈H₂₃N
• 分子量: 253.387
• InChiKey: SZNJDYVDCGBJEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-碘丁烷 、 N-Benzylidenebenzylamine N-oxide 在 indium 、 copper(l) iodide 作用下， 以 水 为溶剂， 反应 24.0h， 以80%的产率得到N-benzyl-(1-phenyl-2-methyl-butyl)amine
  参考文献：
  名称：

  Indium (Zinc)−Copper-Mediated Barbier-Type Alkylation Reaction of Nitrones in Water: Synthesis of Amines and Hydroxylamines

  摘要：

  An efficient method for the Barbier-type alkylation reaction of various nitrones (including chiral version) and alkyl halides in water is described. The amines and hydroxylamines can be obtained in good yields, depending on the judicious choice of the metal complexes used.

  DOI：

  10.1021/ol8027362

文献信息

• Unprecedented Nucleophilic Additions of Highly Polar Organometallic Compounds to Imines and Nitriles Using Water as a Non-Innocent Reaction Medium
  作者：Giuseppe Dilauro、Marzia Dell'Aera、Paola Vitale、Vito Capriati、Filippo Maria Perna

  DOI：10.1002/anie.201705412

  日期：2017.8.14

  inert atmospheres with dry volatile organic solvents and often low temperatures, the addition of highly polar organometallic compounds to non‐activated imines and nitriles proceeds quickly, efficiently, and chemoselectively with a broad range of substrates at room temperature and under air with water as the only reaction medium. Secondary amines and tertiary carbinamines are furnished in yields of up to

  与在惰性气氛下使用干燥的挥发性有机溶剂并通常在低温下进行的经典方法相比，在非活化的亚胺和腈中向非活化亚胺和腈中添加高极性有机金属化合物可快速，高效且在室温下对多种底物进行化学选择性并在空气中以水为唯一反应介质。仲胺和叔卡宾胺的收率高达99％以上。在有机亚胺化合物向亚胺的水上亲核加成中观察到的显着的溶剂D / H同位素效应表明，水上催化源自质子跨有机-水界面的转移。水分子之间的强分子间氢键可能在不利于质子分解的过程中起关键作用，在其他质子传递介质（例如甲醇）中广泛存在。这项工作为重塑水中许多基本的s-block金属介导的有机转化奠定了基础。
• Indium−Copper-Mediated Barbier−Grignard-Type Alkylation Reaction of Imines in Aqueous Media
  作者：Zhi-Liang Shen、Teck-Peng Loh

  DOI：10.1021/ol702263b

  日期：2007.12.1

  developed for Barbier-Grignard-type alkylation reactions of simple imines, using a one-pot condensation of various aldehydes, amines (including aliphatic and chiral version), and alkyl iodides in water or aqueous media. The reactions proceeded efficiently at room temperature to give the desired products in moderate to good yields. Good diastereoselectivities were obtained when using L-valine methyl

  开发了一种有效的In / CuI / InCl3系统，用于在水或水性介质中一锅缩合各种醛，胺（包括脂肪族和手性版本）和烷基碘的简单亚胺的Barbier-Grignard型烷基化反应。反应在室温下有效地进行，以中等至良好的产率得到所需的产物。当使用L-缬氨酸甲酯作为底物时，获得了良好的非对映选择性。
• Indium–Silver- and Zinc–Silver-Mediated Barbier–Grignard-Type Alkylation Reactions of Imines by Using Unactivated Alkyl Halides in Aqueous Media
  作者：Zhi-Liang Shen、Hao-Lun Cheong、Teck-Peng Loh

  DOI：10.1002/chem.200701468

  日期：2008.2.18

  efficient and practical method for the Barbier-Grignard-type alkylation reactions of simple imines by using a one-pot condensation of various aldehydes, amines (including the aliphatic and chiral version), and secondary alkyl iodides has been developed. The reaction proceeded more efficiently in water than in organic solvents. Without the use of CuI, it mainly gave the imine self-reductive coupling product

  在In或Zn / AgI / InCl（3）存在的情况下，通过使用一锅缩合的各种醛，胺（包括脂肪族和手性化合物）的简单亚胺进行Barbier-Grignard型烷基化反应的高效实用方法版本），并且已经开发了仲烷基碘。该反应在水中比在有机溶剂中更有效地进行。不使用CuI，它主要得到亚胺自还原偶联产物，它不是烷基化产物。当使用L-缬氨酸甲酯作为底物时，获得了良好的非对映选择性（高达92：8 dr）。
• PROCESS FOR PRODUCING 1-SUBSTITUTED TRANS-4-(SUBSTITUTED AMINO) PIPERIDIN-3-OL
  申请人：Aikawa Toshiaki

  公开号：US20110172431A1

  公开（公告）日：2011-07-14

  A process is provided for producing a 1-substituted trans-4-(substituted amino)piperidin-3-ol represented by formula (III-1): The process includes a step of reacting a 1-substituted-3,4-epoxypiperidine represented by formula (I): with an amine compound represented by formula (II) in the presence of an inorganic lithium salt. By utilizing the process, trans-4-aminopiperidin-3-ol compounds useful as various chemical products, such as medicine intermediates, can be produced.

  提供了一种生产1-取代的反式-4-(取代氨基)哌啶-3-醇的过程，其化学式为(III-1)：该过程包括以下步骤：将一种化学式为(I)的1-取代-3,4-环氧哌啶与一种化学式为(II)的胺化合物在无机锂盐存在下反应。通过利用该过程，可以生产用途广泛的反式-4-氨基哌啶-3-醇化合物，如药物中间体等化学产品。
• PROCESS FOR PRODUCING 1-SUBSTITUTED TRANS-4-(SUBSTITUTED AMINO)PIPERIDIN-3-OL
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2351738A1

  公开（公告）日：2011-08-03

  A process for producing a 1-substituted trans-4-(substituted amino)piperidin-3-ol represented by formula (III-1): wherein R1 represents an aromatic carbocyclic group, an alkyl group having 1 to 12 carbon atoms which may be substituted with one or more aromatic carbocyclic groups, an alkenyl group having 2 to 14 carbon atoms which may be substituted with one or more aromatic carbocyclic groups, or an alkynyl group having 2 to 12 carbon atoms which may be substituted with one or more aromatic carbocyclic groups, and the like, which comprises a step of reacting a 1-substituted-3,4-epoxypiperidine represented by formula (I): with an amine compound represented by formula (II) in the presence of an inorganic lithium salt. By utilizing the process, trans-4-aminopiperidin-3-ol compounds useful as various chemical products, such as medicine intermediates, can be produced.

  一种生产式 (III-1) 所代表的 1-取代反式-4-(取代氨基)哌啶-3-醇的工艺： 其中 R1 代表芳香族碳环基团、具有 1 至 12 个碳原子且可被一个或多个芳香族碳环基团取代的烷基、具有 2 至 14 个碳原子且可被一个或多个芳香族碳环基团取代的烯基、或具有 2 至 12 个碳原子且可被一个或多个芳香族碳环基团取代的炔基等、 其中包括使式（I）代表的 1-取代-3,4-环氧哌啶反应的步骤： 与式 (II) 所代表的胺化合物反应 在无机锂盐存在下进行。利用该工艺可生产出反式-4-氨基哌啶-3-醇化合物，该化合物可用作各种化学产品，如医药中间体。