4-(1H-benzo[d][1,2,3]triazol-1-yl)butan-2-one | 2038-93-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 4-(1H-benzo[d][1,2,3]triazol-1-yl)butan-2-one
• 英文别名: 4-(benzotriazol-1-yl)-2-butanone；4-benzotriazol-1-yl-butan-2-one；1-<3-Oxo-butyl>-benztriazol；4-(Benzotriazol-1-yl)butan-2-one
• CAS: 2038-93-9
• 化学式: C₁₀H₁₁N₃O
• mdl: MFCD00963795
• 分子量: 189.217
• InChiKey: CIHZUALRGFSWGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(1H-benzo[d][1,2,3]triazol-1-yl)butan-2-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.75h， 以89%的产率得到4-(benzotriazol-1-yl)-butan-2-ol
  参考文献：
  名称：

  制备各种对映体纯的（苯并三唑-1-基）-和（苯并三唑-2-基）-烷-2-醇

  摘要：

  （S）-（-）-（Benzotriazol-1-yl）-和（S）-（-）-（benzotriazol-2-yl）-alkan-2-ols 7a - 9a，7b - 9b及其（R） -（+）-乙酸盐10a – 12a和10b – 12b通过荧光假单胞菌（Amano AK）的脂肪酶以高对映体过量的形式制备，其中乙酸叔丁酯催化外消旋醇4a – 6a和4b – 6b的对映选择性乙酰化。-丁基甲基醚或甲苯，在23°C下。该转化的对映选择性取决于E值为30至57的烷基链的长度。由1 H-苯并三唑和相应的卤代酮合成了数个苯并三唑取代的酮1a – 3a和1b – 3b。在水中或含有5％v / v的水的有机溶剂中，在30°C下用贝克酵母将这些化合物进行立体选择性还原，得到（S）-（-）-醇。在外消旋醇4a - 6a和4b - 6b的动力学拆分中观察到更好的立体选择性（ee = 69–92％，转化率为44–5

  DOI：

  10.1016/j.tetasy.2006.08.019
• 作为产物：
  描述：

  T406石油添加剂 、 丁烯酮 反应 24.0h， 以53%的产率得到4-(1H-benzo[d][1,2,3]triazol-1-yl)butan-2-one
  参考文献：
  名称：

  Green, efficient and practical Michael addition of arylamines to α,β-unsaturated ketones

  摘要：

  The aza-Michael addition of aromatic amines to alpha,beta-unsaturated ketones was carried out effectively at room temperature in good to excellent yields without any catalyst or solvent. It was significant that part of adducts could be collected in almost quantitative yield without column chromatography. This procedure offered a green, efficient, and practical approach for the synthesis of beta-amino ketones. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.082

文献信息

• Uncatalysed intermolecular aza-Michael reactions
  作者：Florian Medina、Nathalie Duhal、Christophe Michon、Francine Agbossou-Niedercorn

  DOI：10.1016/j.crci.2012.11.001

  日期：2013.4

  Résumé The catalyst-free reactions of activated alkenes with primary and secondary amines were investigated leading to various mono- and di-hydroamination products, the latter being rare and original. These reactions were shown to depend first on the strength of the nucleophile. Temperature and steric hindrance of the reagents were the other key factors controlling the selectivity of these aza-Michael reactions. In spite of their poor nucleophilicities, some N-heterocyclic amines could react with different activated alkenes affording valuable intermediates. Such results tended to demonstrate the hydrogen-bonding interactions between activated alkenes and poly-nitrogen aromatic cycles may control these concerted or fully conjugate aza-Michael additions. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.doc

  简历 摘要 研究了活性烯烃与一级和二级胺的无催化剂反应，生成多种单氢胺化和双氢胺化产物，后者较为罕见且具有原创性。这些反应首先取决于亲核试剂的强度。温度和试剂的立体阻碍是控制这些氮杂迈克尔反应选择性的其他关键因素。尽管某些含氮杂环胺的亲核性较差，但它们仍能与不同的活性烯烃反应，生成有价值的中间体。这些结果倾向于表明，活性烯烃与多氮芳香环之间的氢键相互作用可能控制这些协同或完全共轭的氮杂迈克尔加成反应。 补充材料： 本文的补充材料以单独文件提供： mmc1.doc
• Tri- and bi-cyclic heteroaryl histamine-3 receptor ligands
  申请人：Altenbach J. Robert

  公开号：US20050272736A1

  公开（公告）日：2005-12-08

  Compounds of formula (I) wherein R 1 or R 2 is a tricyclic or bicyclic ring, each of which contains at least two heteroatoms, and R 1 , R 2 , R 3 , R 3a , R 3b , R 4 , R 5 , L, X, X′, Y, Y′, Z, and Z′ are as defined herein, are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands. Also disclosed are pharmaceutical compositions comprising the histamine-3 receptor ligands, methods for using such compounds and compositions, and a process for preparing compounds within the scope of formula (I).

  式（I）中R1或R2为含有至少两个杂原子的三环或二环环，其中R1、R2、R3、R3a、R3b、R4、R5、L、X、X′、Y、Y′、Z和Z′如本文所定义，在预防或改善组织胺-3受体配体引起的病症或紊乱方面具有治疗作用。还公开了包含组织胺-3受体配体的药物组合物，使用这类化合物和组合物的方法，以及制备符合式（I）范围内化合物的过程。
• Tri-and bi-cyclic heteroaryl histamine-3 receptor ligands
  申请人：Altenbach J. Robert

  公开号：US20050256309A1

  公开（公告）日：2005-11-17

  Compounds of formula (I) wherein R 1 or R 2 is a tricyclic or bicyclic ring, each of which contains at least two heteroatoms, and R 1 , R 2 , R 3 , R 3a , R 3b , R 4 , R 5 , L, X, X′, Y, Y′, Z, and Z′ are as defined herein, are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands. Also disclosed are pharmaceutical compositions comprising the histamine-3 receptor ligands, methods for using such compounds and compositions, and a process for preparing compounds within the scope of formula (I).

  式（I）中R1或R2为含有至少两个杂原子的三环或二环环，其中R1、R2、R3、R3a、R3b、R4、R5、L、X、X′、Y、Y′、Z和Z′如本文所定义，在预防或改善组织胺-3受体配体引起的病症或紊乱方面具有治疗作用。还公开了包含组织胺-3受体配体的药物组合物，使用这类化合物和组合物的方法，以及制备符合式（I）范围内化合物的方法。
• Borinic Acid Catalyzed Regioselective <i>N</i>-Alkylation of Azoles
  作者：Shrey P. Desai、Matthew T. Zambri、Mark S. Taylor

  DOI：10.1021/acs.joc.2c00281

  日期：2022.4.15

  described. In the presence of diphenylborinic acid (Ph2BOH) and an amine cocatalyst, heterocyclic nucleophiles such as 1,2,3- and 1,2,4-triazoles, substituted tetrazoles, and purine are activated toward selective N-functionalization. The scope of electrophilic partners includes enones, 2-vinylpyridine, phenyl vinyl sulfone, a dehydroalanine derivative, and epoxides. Mechanistic studies, including in situ

  描述了一种用烯烃或环氧化物亲电子试剂对周围的唑型杂环进行区域选择性N-烷基化的方法。在二苯基硼酸 (Ph 2 BOH) 和胺助催化剂的存在下，杂环亲核试剂如 1,2,3-和 1,2,4-三唑、取代的四唑和嘌呤被活化为选择性N官能化。亲电子伙伴的范围包括烯酮、2-乙烯基吡啶、苯基乙烯基砜、脱氢丙氨酸衍生物和环氧化物。讨论了机理研究，包括原位11 B NMR 光谱和动力学分析。
• Katritzky, A. R.; Rachwal, S.; Hughes, C. V., Polish Journal of Chemistry, 1992, vol. 66, # 10, p. 1633 - 1652
  作者：Katritzky, A. R.、Rachwal, S.、Hughes, C. V.、Wang, Z.

  DOI：——

  日期：——