N,N-bis(4-methoxyphenyl)octylamine | 172782-56-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-bis(4-methoxyphenyl)octylamine
• 英文别名: 4-methoxy-N-(4-methoxyphenyl)-N-octylaniline
• CAS: 172782-56-8
• 化学式: C₂₂H₃₁NO₂
• 分子量: 341.494
• InChiKey: XEHHDHKVOQYMMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氯苯甲醚 、 N-辛基对甲氧基苯胺 在 Pd-PEPPSI-IPentCl 、 sodium t-butanolate 作用下， 以 氘代苯 为溶剂， 生成 N,N-bis(4-methoxyphenyl)octylamine
  参考文献：
  名称：

  伯烷基胺和仲苯胺在Pd-NHC催化胺化反应中的速率和计算研究：用NHC配体合理化单芳基化和二芳基化的选择性。

  摘要：

  已经测量了伯烷基胺与不同的Pd-NHC催化剂的相对芳基化速率，以及仲苯胺产物的相对芳基化速率，以试图理解对单芳基化胺产品具有高选择性所必需的关键配体设计特征。随着NHC的N-芳基环上的取代基尺寸增加，单芳基化的选择性增加，并且通过氯化NHC环的背面进一步提高了单芳基化的选择性。为了理解用不同催化剂获得的选择性，已经对该转化的催化循环进行了计算。

  DOI：

  10.1002/chem.201903362

文献信息

• Selective Monoarylation of Primary Amines Using the Pd-PEPPSI-IPent^ClPrecatalyst
  作者：Sepideh Sharif、Richard P. Rucker、Nalin Chandrasoma、David Mitchell、Michael J. Rodriguez、Robert D. J. Froese、Michael G. Organ

  DOI：10.1002/anie.201502822

  日期：2015.8.10

  A single set of reaction conditions for the palladium‐catalyzed amination of a wide variety of (hetero)aryl halides using primary alkyl amines has been developed. By combining the exceptionally high reactivity of the Pd‐PEPPSI‐IPentCl catalyst (PEPPSI=pyridine enhanced precatalyst preparation, stabilization, and initiation) with the soluble and nonaggressive sodium salt of BHT (BHT=2,6‐di‐tert‐butyl‐hydroxytoluene)

  已经开发了使用伯烷基胺对钯催化的多种（杂）芳基卤化物进行胺化反应的一套反应条件。通过将Pd-PEPPSI-IPent Cl催化剂的超高反应性（PEPPSI =吡啶增强的预催化剂的制备，稳定化和引发）与BHT的可溶性非侵蚀性钠盐（BHT = 2,6-二叔丁基-六元和五元（杂）芳基卤化物都经过高效且选择性的胺化作用。
• Efficient and Versatile Buchwald-Hartwig Amination of (Hetero)aryl Chlorides Using the Pd-PEPPSI-IPr^(NMe2)2Precatalyst in the Presence of Carbonate Base
  作者：Yin Zhang、Vincent César、Guy Lavigne

  DOI：10.1002/ejoc.201500030

  日期：2015.3

  precatalyst Pd-PEPPSI-IPr(NMe2)2, in which the IPr ligand was modified by attachment of two dimethylamino groups on to the 4- and 5-positions of the imidazolyl heterocycle, was found to show high catalytic efficiency in the Buchwald-Hartwig amination under mild conditions using Cs2CO3 as a weak base, using a low catalyst loading of 1 mol-%. The protocol is applicable to aryl chlorides bearing base-sensitive

  发现前催化剂 Pd-PEPPSI-IPr(NMe2)2 中的 IPr 配体通过将两个二甲氨基连接到咪唑基杂环的 4 位和 5 位进行修饰，在 Buchwald-在温和条件下使用 Cs2CO3 作为弱碱进行 Hartwig 胺化，使用 1 mol% 的低催化剂负载量。该协议适用于带有碱敏感取代基的芳基氯化物，例如 4-氯苯乙酮与苯胺的偶联。它还可以与空前广泛的胺一起使用，包括强碱性仲烷基胺、伯芳基胺和伯烷基胺。
• Well-defined NHC–Pd(II)–Im (NHC=N-heterocyclic carbene; Im=1-methylimidazole) complex catalyzed C–N coupling of primary amines with aryl chlorides
  作者：Lei Zhu、Yue-Mei Ye、Li-Xiong Shao

  DOI：10.1016/j.tet.2012.01.008

  日期：2012.3

  We report herein a well-defined NHC-Pd(II)-Im(NHC=N-heterocyclic carbene; Im=1-methylimidazole) complex catalyzed C-N coupling of primary amines with aryl chlorides. Under the optimal reaction conditions, a variety of primary amines can be coupled with aryl chlorides to give the amination products in good to high yields within 4 h. It is worthy of noting here that the NHC-Pd(II)-Im complex showed especially high catalytic activity toward challenging sterically hindered substrates including both of aryl amines and aryl chlorides. In addition, alkyl amines were also proved to be suitable reaction partners to give the corresponding amination products in good to high yields. (C) 2012 Elsevier Ltd. All rights reserved.
• Rate and Computational Studies for Pd‐NHC‐Catalyzed Amination with Primary Alkylamines and Secondary Anilines: Rationalizing Selectivity for Monoarylation versus Diarylation with NHC Ligands
  作者：Christopher Lombardi、Richard P. Rucker、Robert D. J. Froese、Sepideh Sharif、Pier Alexandre Champagne、Michael G. Organ

  DOI：10.1002/chem.201903362

  日期：2019.11.7

  have been measured, as have the relative rates of arylation of the secondary aniline product in an attempt to understand the key ligand design features necessary to have high selectivity for the monoarylated amine product. As the substituents on the N-aryl ring of the NHC increase in size, selectivity for monoarylation increases and this is further enhanced by chlorinating the back of the NHC ring.

  已经测量了伯烷基胺与不同的Pd-NHC催化剂的相对芳基化速率，以及仲苯胺产物的相对芳基化速率，以试图理解对单芳基化胺产品具有高选择性所必需的关键配体设计特征。随着NHC的N-芳基环上的取代基尺寸增加，单芳基化的选择性增加，并且通过氯化NHC环的背面进一步提高了单芳基化的选择性。为了理解用不同催化剂获得的选择性，已经对该转化的催化循环进行了计算。