N-(3,5-di-tert-butyl-4-hydroxybenzyl)-N-phenylamine | 32559-14-1

• 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-(3,5-di-tert-butyl-4-hydroxybenzyl)-N-phenylamine
• 英文别名: (3,5-di-tert-butyl-4-hydroxybenzyl)(phenyl)amine；N-(3,5-di-tert-butyl-4-hydroxybenzyl)aniline；2,6-di-tert-butyl-4-((phenylamino)methyl)phenol；N-Phenyl-3.5-di-tert-butyl-4-hydroxybenzylamin；4-(Anilinomethyl)-2,6-di-tert-butylphenol；4-(anilinomethyl)-2,6-ditert-butylphenol
• CAS: 32559-14-1
• 化学式: C₂₁H₂₉NO
• 分子量: 311.467
• InChiKey: LIGJHWSYVIBRGG-UHFFFAOYSA-N

物化性质

• 熔点：
  104-105 °C
• 沸点：
  399.3±37.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3,5-di-tert-butyl-4-hydroxybenzyl)-N-phenylamine 、 对甲苯磺酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 18.0h， 生成
  参考文献：
  名称：

  Inhibitors of lipoprotein(a) assembly

  摘要：

  Compounds of the general structure A and B were investigated for their activity as lipoprotein(a), [Lp(a)], assembly (coupling) inhibitors. SAR around the amino acid derivatives (structure A) gave compound 14-6 as a potent coupling inhibitor. Oral closing of compound 14-6 to Lp(a) transgenic mice and cymologous monkeys resulted in a > 30% decrease in plasma Lp(a) levels after 1-2 weeks of treatment at 100 mg/kg/day.) (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2002.04.001
• 作为产物：
  描述：

  苯胺 、 3,5-二叔丁基-4-羟基苯甲醛 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 生成 N-(3,5-di-tert-butyl-4-hydroxybenzyl)-N-phenylamine
  参考文献：
  名称：

  Inhibitors of lipoprotein(a) assembly

  摘要：

  Compounds of the general structure A and B were investigated for their activity as lipoprotein(a), [Lp(a)], assembly (coupling) inhibitors. SAR around the amino acid derivatives (structure A) gave compound 14-6 as a potent coupling inhibitor. Oral closing of compound 14-6 to Lp(a) transgenic mice and cymologous monkeys resulted in a > 30% decrease in plasma Lp(a) levels after 1-2 weeks of treatment at 100 mg/kg/day.) (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2002.04.001

文献信息

• Metal-free transamidation of benzoylpyrrolidin-2-one and amines under aqueous conditions
  作者：Devaneyan Joseph、Myeong Seong Park、Sunwoo Lee

  DOI：10.1039/d1ob00967b

  日期：——

  in the presence of DTBP and TBAI to afford the transamidated products in good yields. The reactions were conducted under aqueous conditions and good functional group tolerance was achieved. Both aliphatic and aromatic primary amines displayed good activity under metal-free conditions. A radical reaction pathway is proposed.

  N-酰基内酰胺酰胺，如苯甲酰吡咯烷-2-酮、苯甲酰哌啶-2-酮和苯甲酰西泮-2-酮在DTBP和TBAI存在下与胺反应，以良好的收率得到转酰胺基产物。该反应在水性条件下进行，并获得了良好的官能团耐受性。脂肪族和芳香族伯胺在无金属条件下均表现出良好的活性。提出了一种自由基反应途径。
• Switchable Radical Carbonylation by Philicity Regulation
  作者：Bin Lu、Minghao Xu、Xiaotian Qi、Min Jiang、Wen-Jing Xiao、Jia-Rong Chen

  DOI：10.1021/jacs.2c06677

  日期：2022.8.17

  acyl radical to form the relatively stabilized cyanoalkyl acyl-DMAP salts that engaged in the subsequent substitution with the nucleophilic amines to produce the single carbonylation products. The reaction proceeded smoothly with excellent selectivity in the presence of various amine nucleophiles at room temperature, generating valuable amides and α-ketoamides in a versatile and controlled fashion.

  涉及作为容易获得的 C1 合成子的 CO 的羰基化反应已成为从原料化学品构建羰基化合物的最重要工具之一。尽管有许多通过离子或自由基途径进行羰基化反应的催化方法，但这些方法的一个固有限制是需要控制从相同和简单的起始材料中可转换的单羰基化和双羰基化形成增值产品。在这里，我们描述了一种新策略，该策略利用光氧化还原催化来调节胺偶联配偶体的亲水性，从而驱动可切换的自由基羰基化反应。在双羰基化中，胺首先通过单电子转移氧化转化为氮自由基阳离子并与CO偶联形成氨基甲酰基自由基，其进一步与起始的氰基烷基酰基自由基进行自由基交叉偶联以提供双羰基化产物。在添加化学计量的 4-二甲氨基吡啶 (DMAP) 后，DMAP 竞争性地捕获最初形成的氰基烷基酰基自由基以形成相对稳定的氰基烷基酰基-DMAP 盐，该盐参与随后的亲核胺取代以产生单一羰基化产物。在室温下，在各种胺类亲核试剂存在下，反应以优异的选择性顺利进行，以通用和可控的方式生成有价值的酰胺和
• ——
  作者：S. V. Bukharov、G. N. Nugumanova、N. A. Mukmeneva

  DOI：10.1023/a:1024910004024

  日期：——

  The acid dissociation of 3,5-di-tert-butyl-4-hydroxybenzyl acetate in the presence of bases or in dimethylformamide favors reaction of this compound with weakly basic nucleophilies.
• ——
  作者：S. V. Bukharov、V. V. Syakaev、S. N. Pod''yachev、G. N. Nugumanova、N. A. Mukmeneva

  DOI：10.1023/a:1020490525414

  日期：——

  Solvolysis of 3,5-di-tert-butyl-4-hydroxybenzyl acetate in alcohol solutions involves intermediate-formation of 2,6-di-tert-butyl-4-methylene-1-benzoquinone that further takes up a molecule of the alcohol.
• Inhibitors of lipoprotein(a) assembly
  作者：Karen E Sexton、Helen T Lee、Mark Massa、Janak Padia、William C Patt、Peggy Liao、Jason K Pontrello、Bruce D Roth、Mark A Spahr、Randy Ramharack

  DOI：10.1016/j.bmc.2002.04.001

  日期：2003.11

  Compounds of the general structure A and B were investigated for their activity as lipoprotein(a), [Lp(a)], assembly (coupling) inhibitors. SAR around the amino acid derivatives (structure A) gave compound 14-6 as a potent coupling inhibitor. Oral closing of compound 14-6 to Lp(a) transgenic mice and cymologous monkeys resulted in a > 30% decrease in plasma Lp(a) levels after 1-2 weeks of treatment at 100 mg/kg/day.) (C) 2003 Elsevier Ltd. All rights reserved.