N-(4-methoxybenzyl)-N,N-diphenylamine | 148963-14-8

• 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-methoxybenzyl)-N,N-diphenylamine
• 英文别名: (4-methoxylbenzyl)diphenylamine；N-[(4-methoxyphenyl)methyl]-N-phenylaniline
• CAS: 148963-14-8
• 化学式: C₂₀H₁₉NO
• 分子量: 289.377
• InChiKey: STSHXVASZLRNPN-UHFFFAOYSA-N

物化性质

• 沸点：
  445.0±28.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-methoxybenzyl)-N,N-diphenylamine 在 氧气 作用下， 以 乙腈 为溶剂， 生成 9-[(4-methoxyphenyl)methyl]carbazole
  参考文献：
  名称：

  Comparison of Oxidative and Excited State Cyclizations of N-Benzyldiphenylamines to N-Benzylcarbazoles

  摘要：

  Pulse radiolysis of a family of N-benzyldiphenylamines in aerated cyclohexane results in oxidative cyclization products, i.e., the corresponding N-benzylcarbazoles, as does direct photolysis at 254 nm. Chemical oxidation and bulk electrolysis lead to benzidine formation as the major product, with the competing cyclization pathway becoming minor. Photoinduced electron transfer sensitization induces formation of a radical ion pair in which back electron transfer quenches net reaction. No significant amounts of products deriving from bond cleavage of an intermediate cation radical could be detected in any of the reactions. AM1 calculations show lower barriers for the initial cyclization through a triplet state than through an intermediate cation radical or dication.

  DOI：

  10.1021/ja00103a014
• 作为产物：
  描述：

  N,N-二苯基-4-甲氧基苯甲酰胺 在 三氟甲磺酸酐 、 二氢吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 以50%的产率得到N-(4-methoxybenzyl)-N,N-diphenylamine
  参考文献：
  名称：

  叔酰胺的高化学选择性无金属还原

  摘要：

  该通讯描述了叔酰胺通过无金属化学选择性还原为相应胺的过程。Hantzsch 酯用作温和的还原剂，用于还原三氟甲磺酸酐活化的酰胺，提供具有高官能团耐受性的叔胺。

  DOI：

  10.1021/ja077463q

文献信息

• Direct reductive amination using triethylsilane and catalytic bismuth(III) chloride
  作者：Takehiko Matsumura、Masahisa Nakada

  DOI：10.1016/j.tetlet.2014.01.132

  日期：2014.3

  Direct reductive amination (DRA) using triethylsilane (TESH) and catalytic bismuth(III) chloride (BiCl3) is described for the first time. The use of TESH and BiCl3 provides easy handling, low cost, non-toxicity, and a mild Lewis acid activity, thereby meeting the demand for green and sustainable chemistry. The developed DRA is highly chemoselective and applicable to less-basic amines. The experimental

  首次描述了使用三乙基硅烷（TESH）和催化氯化铋（III）（BiCl 3）的直接还原胺化（DRA）。TESH和BiCl 3的使用提供了易于处理，低成本，无毒和温和的路易斯酸活性，从而满足了对绿色和可持续化学的需求。研发的DRA具有高度的化学选择性，适用于碱性较低的胺。这项研究的实验结果表明，发达的DRA可以被BiCl 3催化，通过TESH可以逐渐将其还原为Bi（0）或低价的铋，而TESCl，Bi（0）和Bi（0）可以被BiSH 3催化。TESC1在一定程度上催化了DRA。
• Concise synthesis of aromatic tertiary amines via a double Petasis–borono Mannich reaction of aromatic amines, formaldehyde, and organoboronic acids
  作者：Jiayi Wang、Pinzhen Li、Qiaoying Shen、Gonghua Song

  DOI：10.1016/j.tetlet.2014.03.131

  日期：2014.7

  A simple and efficient strategy to construct aromatic tertiary amines via a double Petasis–borono Mannich reaction of aromatic amines, formaldehyde, and organoboronic acids has been developed. The transformation provides a useful method for the synthesis of amine derivatives.

  通过芳香胺，甲醛和有机硼酸的双重Petasis-borono Mannich反应，开发了一种简单有效的方法来构建芳香叔胺。该转化为合成胺衍生物提供了有用的方法。
• One-pot reductive amination of aldehydes catalyzed by a hydrio-iridium(III) complex in aqueous medium
  作者：Rung-Yi Lai、Chun-I. Lee、Shiuh-Tzung Liu

  DOI：10.1016/j.tet.2007.11.079

  日期：2008.2

  A combination of sodium tetrakis[3,5-di(trifluoromethyl)phenyl]borate [NaBArF4] and hydrio-iridium(III) complex efficiently catalyzed the one-pot reductive amination of aldehydes with various amines and ammonia in water under mild conditions in good to excellent yields.

  四[3,5-二（三氟甲基）苯基]硼酸钠[NaBAr F 4 ]和氢铱（III）配合物的组合可在温和条件下有效催化水中的各种胺和氨进行一锅还原醛化胺化反应产量高到极好。
• A Simple and Convenient Method for the Synthesis of N,N-Diaryl Tertiary Amines
  作者：Michael Findlater、Francis Wekesa、Neha Phadke、Claire Jahier、David Cordes

  DOI：10.1055/s-0033-1340820

  日期：——

  Abstract Direct preparation of tertiary amines in which two substituents are aromatic is described. In the presence of either the inorganic base sodium tert-butoxide or the sterically hindered organic base diisopropylethylamine, the alkylation of secondary diarylamines is achieved smoothly. In contrast to methods previously reported in the literature, this procedure is high-yielding and does not require

  摘要 描述了直接制备其中两个取代基为芳族的叔胺的方法。在无机碱叔丁醇钠或位阻有机碱二异丙基乙胺的存在下，仲二芳基胺的烷基化可顺利实现。与先前文献中报道的方法相比，该方法收率高，并且不需要使用过渡金属催化剂或不溶于官能团的氢化物还原剂。 描述了直接制备其中两个取代基为芳族的叔胺的方法。在无机碱叔丁醇钠或位阻有机碱二异丙基乙胺的存在下，仲二芳基胺的烷基化可顺利实现。与先前文献中报道的方法相比，该方法收率高，并且不需要使用过渡金属催化剂或不溶于官能团的氢化物还原剂。
• Multifunctionalized polyethylene glycol derivative and preparation method therefor
  申请人：XIAMEN SINOPEG BIOTECH CO., LTD.

  公开号：US11324827B2

  公开（公告）日：2022-05-10

  Disclosed are a multifunctionalized polyethylene glycol derivative and a preparation method therefor. The derivative has an H-shaped structure as represented by formula (1) and comprises one linear core LPEG and four PEG branch chains, where n1, n2, n3, and n4 respectively are the degrees of polymerization of the branch chains, U1 and U2 are trivalent branching groups connecting the core LPEG to two of the PEG branch chains, F1 and F2 contain a functional group or a protected form R01 thereof and may or may not contain a branched group G, correspondingly, the number of R01 is one or more, F1 and F2 are either identical or different, any one linking group in the molecule or any linking group formed with an adjacent heteroatom group can either remain stable or be degraded, and any one PEG segment in the molecule is discretely polydispersed or monodispersed. The multifunctional polyethylene glycol is flexible and diverse in terms of branch structures and the lengths of branching arms, has various parameters and performance indicators that are adjustable and easy to control, and has a broad applicability.

  本发明公开了一种多功能聚乙二醇衍生物及其制备方法。该衍生物具有由式（1）表示的 H 型结构，包括一个线性核心 LPEG 和四个 PEG 支链，其中 n1、n2、n3 和 n4 分别为支链的聚合度，U1 和 U2 为连接核心 LPEG 和两个 PEG 支链的三价支化基团、F1 和 F2 含有一个官能团或其保护形式 R01，可以含有或不含有支链基团 G，相应地，R01 的数目为一个或多个，F1 和 F2 要么相同要么不同，分子中的任何一个连接基团或与相邻杂原子基团形成的任何连接基团要么保持稳定，要么降解，分子中的任何一个 PEG 段离散多分散或单分散。多功能聚乙二醇的支链结构和支臂长度灵活多样，各种参数和性能指标可调且易于控制，具有广泛的适用性。