1-苯乙基-1H-苯并[d][1,2,3]三唑 | 63777-68-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 中文名称: 1-苯乙基-1H-苯并[d][1,2,3]三唑
• 英文名称: 1-phenethyl-1H-benzo[d][1,2,3]triazole
• 英文别名: 1-(2-phenethyl)benzotriazole；N-1-phenethylbenzotriazole；1-phenethylbenzotriazole；1-phenethyl-1H-benzotriazole；1-Phenaethyl-1H-benzotriazol；1-(2-phenylethyl)benzotriazole
• CAS: 63777-68-4
• 化学式: C₁₄H₁₃N₃
• 分子量: 223.277
• InChiKey: GBHXISDJTKHBFA-UHFFFAOYSA-N

物化性质

• 沸点：
  405.9±24.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)
• 溶解度：
  2.1 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	[1-(Benzotriazol-1-yl)-2-phenylethyl]-trimethylsilane	——	C17H21N3Si	295.45
  ——	1-(2-phenyl-1-phenylthioethyl)benzotriazole	111198-12-0	C20H17N3S	331.441
  1-甲基苯并三唑	1-methyl-1H-benzo[d][1,2,3]triazole	13351-73-0	C7H7N3	133.153
  ——	1-(2-phenyl-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)ethyl)-1H-benzo[d][1,2,3]triazole	1449418-23-8	C23H30N4O	378.517

反应信息

• 作为反应物：
  描述：

  1-苯乙基-1H-苯并[d][1,2,3]三唑 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以92%的产率得到3-(2-phenylethyl)-3H-1,2,3-benzotriazole 1-oxide
  参考文献：
  名称：

  Conversions by Dimethyldioxirane of 1-Alkylbenzotriazoles into Their N-Oxides and of 2-Alkylbenzotriazoles into 2-Alkyl-trans-4,5,6,7-diepoxy-4,5,6,7-tetrahydrobenzotriazoles

  摘要：

  Dimethyldioxirane converted 1-alkylbenzotriazoles 4 to the corresponding 3-alkylbenzotriazole 1-oxides 5 in good yields, but transformed 2-alkylbenzotriazoles 12 into 2-alkyl-trans-4,5,6,7-diepoxy-4,5,6,7-tetrahydrobenzotriazoles 13.

  DOI：

  10.1021/jo010194g
• 作为产物：
  描述：

  1-iodomethylbenzotriazole 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 1-苯乙基-1H-苯并[d][1,2,3]三唑
  参考文献：
  名称：

  Katritzky, Alan R.; Hughes, Craig V.; Rachwal, Stanislaw, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1579 - 1588

  摘要：

  DOI：

文献信息

• Aqueous Micellar Medium in Organic Synthesis: Alkylations and Michael Reactions of Benzotriazole
  作者：Sabir Hussain Mashraqui、Sukeerthi Kumar、Chandrasekhar Dayal Mudaliar

  DOI：10.1246/bcsj.74.2133

  日期：2001.11

  cetyltrimethylammonium bromide in catalyzing C–N bond formation has been studied with respect to N-alkylations of benzotriazole (Bt). Alkylations with various alkylating agents and the addition of Bt across activated double bonds in the Michael fashion occurred successfully in fair-to-good yields in the aqueous micellar regime. These reactions provided a mixture of N-1 and N-2 alkylated products, with a marked preference

  关于苯并三唑 (Bt) 的 N-烷基化，研究了十六烷基三甲基溴化铵水胶束催化 C-N 键形成的可行性。在水性胶束体系中，用各种烷化剂烷基化和以迈克尔方式在活化的双键上添加 Bt 成功地发生了从公平到良好的产率。这些反应提供了 N-1 和 N-2 烷基化产物的混合物，N-1 异构体明显优于 N-2 异构体。已通过实验评估胶束催化，表明与它们的水性对应物相比，对这些烷基化的胶束贡献超过 50%。由于 N-烷基苯并三唑具有潜在的生物学意义，因此本胶束程序为其他可用方法提供了方便的替代方法。
• Stereoselective Radical Azidooxygenation of Alkenes
  作者：Bo Zhang、Armido Studer

  DOI：10.1021/ol402106x

  日期：2013.9.6

  Radical azidooxygenation of various alkenes is described. A readily prepared N3-iodine(III) reagent acts as a clean N3-radical precursor. Radical generation is achieved with TEMPONa acting as a mild organic reducing reagent. The C-radical generated after N3-radical addition is efficiently trapped by in situ generated TEMPO. Yields are good to excellent, and for cyclic systems azidooxygenation occurs

  描述了各种烯烃的自由基叠氮加氧。易于制备的N 3-碘（III）试剂可作为纯净的N 3-自由基前体。TEMPONa作为温和的有机还原剂可实现自由基的产生。N 3自由基加成后生成的C自由基被原位生成的TEMPO有效地捕获。产率是好还是极好，并且对于循环系统，叠氮加氧以优异的非对映选择性发生。
• Aerobic Electrochemical C_sp³–N Coupling between Aliphatic Carboxylic Acids and N-heterocycles
  作者：Ruonan Chen、Hongyan Yuan、Yawen Wang、Hongyu Chen、Yanhua Zhang

  DOI：10.1021/acs.organomet.2c00455

  日期：2023.1.9

  Csp3–N coupling between aliphatic carboxylic acids and N-heterocycles via electrochemical decarboxylation is reported. Various N-alkylation products are successfully obtained in moderate to good yields in the presence of CF3SO2Na at a constant current in CH3CN under ambient conditions. With the help of the Co(OAc)2·4H2O catalyst, this electrochemical synthesis exhibits satisfying functional-group tolerance

  报道了通过电化学脱羧作用在脂肪族羧酸和 N-杂环之间进行C sp 3 –N 偶联。在环境条件下，在 CH 3 CN 中以恒定电流在 CF 3 SO 2 Na存在下，以中等到良好的收率成功地获得了各种 N-烷基化产物。在 Co(OAc) 2 ·4H 2 O 催化剂的帮助下，这种电化学合成对伯羧酸和仲羧酸都表现出令人满意的官能团耐受性，这在以前的工作中并不适用。
• Compounds that enhance Atoh-1 expression
  申请人：MASSACHUSETTS EYE & EAR INFIRMARY

  公开号：EP2732819A2

  公开（公告）日：2014-05-21

  This invention generally provides compounds, pharmaceutical compositions, and methods for their use, which include methods that result in increased expression in an Atoh1 gene (e.g., Hath1) in a biological cell. More specifically, the invention relates to the treatment of diseases and/or disorders that would benefit from increased Atoh1 expression, e.g. a hearing impairment or imbalance disorder associated with a loss of auditory hair cells, or a disorder associated with abnormal cellular proliferation.

  本发明一般提供化合物、药物组合物及其使用方法，其中包括导致生物细胞中 Atoh1 基因（如 Hath1）表达增加的方法。更具体地说，本发明涉及可从 Atoh1 表达增加中获益的疾病和/或失调症的治疗，例如与听觉毛细胞丧失有关的听力损伤或失调症，或与细胞异常增殖有关的失调症。
• Compounds that enhance Atoh1 expression
  申请人：Massachusetts Eye & Ear Infirmary

  公开号：US10406163B2

  公开（公告）日：2019-09-10

  This invention generally provides compounds, pharmaceutical compositions, and methods for their use, which include methods that result in increased expression in an Atoh1 gene (e.g., Hath1) in a biological cell. More specifically, the invention relates to the treatment of diseases and/or disorders that would benefit from increased Atoh1 expression, e.g., a hearing impairment or imbalance disorder associated with a loss of auditory hair cells, or a disorder associated with abnormal cellular proliferation.

  本发明一般提供化合物、药物组合物及其使用方法，其中包括导致生物细胞中Atoh1基因（如Hath1）表达增加的方法。更具体地说，本发明涉及可从 Atoh1 表达增加中获益的疾病和/或失调症的治疗，例如，与听觉毛细胞丧失有关的听力损伤或失调症，或与细胞异常增殖有关的失调症。