2-溴-4-甲基苯基氨基甲酸叔丁酯 | 364607-53-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-溴-4-甲基苯基氨基甲酸叔丁酯
• 英文名称: tert-butyl (2-bromo-4-methylphenyl)carbamate
• 英文别名: N-BOC 2-Bromo-4-methylaniline；tert-butyl N-(2-bromo-4-methylphenyl)carbamate
• CAS: 364607-53-4
• 化学式: C₁₂H₁₆BrNO₂
• 分子量: 286.169
• InChiKey: PMCPXFWJWZNKJK-UHFFFAOYSA-N

物化性质

• 沸点：
  297.6±33.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2921430090

SDS

2-溴-4-甲基苯基氨基甲酸叔丁酯MSDS英文版

反应信息

• 作为反应物：
  描述：

  2-溴-4-甲基苯基氨基甲酸叔丁酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 四(三苯基膦)钯 sodium acetate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 甲苯 为溶剂， 生成 9-methylbenzo[f][1,7]naphthyridin-5-amine
  参考文献：
  名称：

  [EN] COMPOUNDS AND COMPOSITIONS AS TLR ACTIVITY MODULATORS
  [FR] COMPOSÉS ET COMPOSITIONS SERVANT DE MODULATEURS DE L'ACTIVITÉ DES TLR

  摘要：

  该发明提供了一类新型化合物，包括这些化合物的药物组合物以及使用这些化合物来治疗或预防与Toll样受体相关的疾病或紊乱的方法，包括TLR7和TLR8。在一个方面，这些化合物可用作辅助剂，以增强疫苗的效果（公式I），其中：X3为N；X4为N或CR3；X5为-CR4=CR5。

  公开号：

  WO2009111337A1
• 作为产物：
  描述：

  2-溴-4-甲基苯胺 在 4-二甲氨基吡啶 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 2-溴-4-甲基苯基氨基甲酸叔丁酯
  参考文献：
  名称：

  Indole Synthesis by Controlled Carbolithiation of o-Aminostyrenes

  摘要：

  An effective synthesis of the functionalized indole ring system has been developed from substituted o-aminostyrene starting material. Our methodology involves a novel cascade reaction sequence of alkyllithium addition to the styrene double bond and subsequent trapping of the intermediate organolithium with a suitable electrophile, followed by an in situ ring closure and dehydration to generate the indole ring. This new reaction sequence allows for the introduction of molecular diversity at all positions on the indole scaffold. The procedure was shown to be successful with a range of both C and N substituents on the o-aminostyrenes. The reaction sequence was tolerant to the reactivity range of alkyllithiums such as tert-, sec-, and n-butyllithium. The electrophiles used were DMF, which generated indole products with C-2 unsubstituted, and nitriles, which incorporated the nitrile substituent at C-2. The o-aminostyrene starting materials were generated by a Pd-catalyzed cross-coupling reaction of a vinyl boronic acid equivalent with the readily available substituted o-bromoanilines.

  DOI：

  10.1021/jo048723e

文献信息

• Palladium-Catalyzed Carbamate-Directed Regioselective Halogenation: A Route to Halogenated Anilines
  作者：Firouz Matloubi Moghaddam、Ghazal Tavakoli、Borna Saeednia、Peter Langer、Behzad Jafari

  DOI：10.1021/acs.joc.6b00329

  日期：2016.5.6

  N-arylcarbamates under mild conditions for the first time. Although being weakly coordinating, N-arylcarbamates act very well as a removable directing group for activation of C–H bonds. The developed procedure results in extremely valuable halogenated N-arylcarbmates that can further be hydrolyzed to halogenated anilines. The obtained reaction conditions showed broad scope and wide functional group tolerance

  这项研究首次描述了一种在温和条件下对N-芳基氨基甲酸酯进行邻位选择性卤化的有效方法。N-芳基氨基甲酸酯虽然协调性较弱，但可作为活化C-H键的可移动的导向基团发挥很好的作用。所开发的方法产生了非常有价值的卤代N-芳基氨基甲酸酯，其可以进一步水解为卤代苯胺。所获得的反应条件显示出宽范围和宽泛的官能团耐受性。所有产品均以极高的选择性高收率形成。
• NHC-Catalyzed Atroposelective Acylation of Phenols: Access to Enantiopure NOBIN Analogs by Desymmetrization
  作者：Shenci Lu、Si Bei Poh、Zi-Qiang Rong、Yu Zhao

  DOI：10.1021/acs.orglett.9b02425

  日期：2019.8.2

  Herein we present a highly efficient N-heterocyclic-carbene (NHC)-catalyzed atroposelective acylation of amino bisphenols to provide access to a wide range of 1,1′-biaryl-2,2′-amino alcohols (NOBIN analogs) in high yield and with uniformly excellent enantioselectivity. This catalytic system is shown to proceed through a combination of desymmetrization and secondary kinetic resolution to produce the axially

  本文中，我们介绍了一种高效的N-杂环卡宾（NHC）催化的氨基双酚atroposelective酰化反应，以高产率提供广泛的1,1'-biaryl-2,2'-氨基醇（NOBIN类似物）并具有一致优异的对映选择性。已显示该催化体系通过脱对称和二级动力学拆分的组合进行，以产生具有优异对映选择性的轴向手性产物。
• Rhodium-Catalyzed Tandem Conjugate Addition−Mannich Cyclization Reaction: Straightforward Access to Fully Substituted Tetrahydroquinolines
  作者：So Won Youn、Ju-Hyun Song、Dai-Il Jung

  DOI：10.1021/jo800914c

  日期：2008.7.1

  A new Rh(I)-catalyzed tandem conjugate addition−Mannich cyclization reaction of imine-substituted electron-deficient alkenes with arylboronic acids has been developed to afford 2,3,4-trisubstituted 1,2,3,4-tetrahydroquinolines. This is the first example involving imine group as a secondary electrophile in Rh(I)-catalyzed tandem reactions.

  已开发出一种新的Rh（I）催化的串联共轭加成反应-亚胺取代的电子缺陷烯烃与芳基硼酸的曼尼希环化反应，得到2,3,4-三取代的1,2,3,4-四氢喹啉。这是第一个涉及亚胺基作为Rh（I）催化串联反应中的第二亲电子试剂的例子。
• A Rh(II)- or Ag(I)-Catalyzed Formal C–O Bond Insertion of Cyclic Hemiaminal with Aryl Diazoacetate
  作者：Wenhao Hu、Cong Xu、Xiangrong Liu、Xiongda Xie、Lin Deng、Xinfang Xu、Albert S. C. Chan

  DOI：10.1055/a-1623-1490

  日期：2021.12

  This method provides an efficient way to construct six- and seven-membered N-heterocycles containing a biaryl linkage. This reaction features a gem-difunctionalization process of diazo compounds with cyclic hemiaminals, delivering α-hydroxyl-β-amino ester derivatives with a tertiary carbon center through a formal C–O bond-insertion transformation.

  已经开发了一种通过原位生成的两种反应中间体的会聚组装的温和简便的合成方法。该方法提供了一种构建含有联芳基键的六元和七元 N-杂环的有效方法。该反应的特点是重氮化合物与环状半缩醛的双功能化过程，通过正式的 C-O 键插入转化，提供具有叔碳中心的 α-羟基-β-氨基酯衍生物。
• Homogenous suspension of immunopotentiating compounds and uses thereof
  申请人：Skibinski David

  公开号：US09408907B2

  公开（公告）日：2016-08-09

  The present invention generally relates to homogeneous suspensions of small molecule immune potentiators (SMIPs) that are capable of stimulating or modulating an immune response in a subject in need thereof. The homogeneous suspensions may be used in combinations with various antigens or adjuvants for vaccine therapies.

  本发明通常涉及能够刺激或调节受需要者免疫反应的小分子免疫增强剂（SMIPs）的均匀悬浮液。这些均匀悬浮液可以与各种抗原或佐剂结合在一起用于疫苗治疗。