(1H-benzo[d][1,2,3]triazol-1-yl)(naphthalen-2-yl)methanone | 177960-06-4

• 物质功能分类: 化学试剂 - 有机试剂 - 肼
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1H-benzo[d][1,2,3]triazol-1-yl)(naphthalen-2-yl)methanone
• 英文别名: (1H-1,2,3-benzotriazol-1-yl)(naphthalen-2-yl)methanone；1-(2-Naphthoyl) benzotriazole；benzotriazol-1-yl(naphthalen-2-yl)methanone
• CAS: 177960-06-4
• 化学式: C₁₇H₁₁N₃O
• 分子量: 273.294
• InChiKey: BYKCXRMGOQXTMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (1H-benzo[d][1,2,3]triazol-1-yl)(naphthalen-2-yl)methanone 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.25h， 生成 4-hydroxy-6-(2-naphthyl)-2H-pyran-2-one
  参考文献：
  名称：

  Facile Syntheses of 2,2-Dimethyl-6-(2-oxoalkyl)-1,3-dioxin-4-ones and the Corresponding 6-Substituted 4-Hydroxy-2-pyrones

  摘要：

  A variety of 2,2-dimethyl-6-(2-oxoalkyl)-1,3-dioxin-4-ones 5a-l and the corresponding 6-substituted 4-hydroxy-2-pyrones 3a-l were prepared in high yields under mild reaction conditions by the reaction of 2,2,6-trimethyl-1,3-dioxin-4-one 4 with 1-acylbenzotriazoles 9 in the presence of LDA followed by thermal cyclization of 5a-l to 3a-1. Synthesis of novel 6-(1-benzoylalkyl)-2,2-dimethyl-1,3-dioxin-4-ones 12a-c was achieved by alkylation of dioxinone 5a and their subsequent cyclization gave 5-alkyl-4-hydroxy-2-pyrones 13a-c.

  DOI：

  10.1021/jo050307m
• 作为产物：
  描述：

  2-萘甲酸 在 N-溴代丁二酰亚胺(NBS) 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (1H-benzo[d][1,2,3]triazol-1-yl)(naphthalen-2-yl)methanone
  参考文献：
  名称：

  10.3998/ark.5550190.p010.129

  摘要：

  DOI：

  10.3998/ark.5550190.p010.129

文献信息

• Nickel-Catalyzed Reductive Cross-Coupling of <i>N</i>-Acyl and <i>N</i>-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides
  作者：Erdong Qu、Shangzhang Li、Jin Bai、Yan Zheng、Wanfang Li

  DOI：10.1021/acs.orglett.1c03535

  日期：2022.1.14

  Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to

  在此，我们报道了一种方便获得的N-酰基苯并三唑与烷基、烯基和芳基硝基化合物的 Ni 催化还原转酰胺基反应，该反应以良好的收率和广泛的底物范围提供了各种酰胺。相同的催化反应条件也适用于N-磺酰基苯并三唑，它可以与硝基芳烃和硝基烷烃进行平滑的还原偶联，得到相应的磺酰胺。
• Transfer Hydrogenation in Water: Enantioselective, Catalytic Reduction of α-Cyano and α-Nitro Substituted Acetophenones
  作者：Omid Soltani、Martin A. Ariger、Henar Vázquez-Villa、Erick M. Carreira

  DOI：10.1021/ol1008894

  日期：2010.7.2

  Catalytic reduction of α-substituted acetophenones under conditions involving asymmetric transfer hydrogenation in water is described. The reaction is conducted in water and open to air, and formic acid is used as reductant.

  描述了在涉及水中不对称转移氢化的条件下催化还原α-取代的苯乙酮。该反应在水中进行并且对空气开放，并且甲酸用作还原剂。
• Iridium Diamine Catalyst for the Asymmetric Transfer Hydrogenation of Ketones
  作者：Henar Vázquez-Villa、Stefan Reber、Martin A. Ariger、Erick M. Carreira

  DOI：10.1002/anie.201102732

  日期：2011.9.12

  A simple and very efficient chiral aqua iridium(III) diamine complex leads to excellent enantioselectivities in the asymmetric transfer hydrogenation of various α‐cyano and α‐nitro ketones. The catalyst provides the ortho‐substituted aromatic alcohols with especially high ee values. The diamine ligands can be used directly as chiral ligands; conversion into the corresponding sulfamide is not necessary

  一个简单而高效的手性水合铱（III）二胺络合物可在各种α-氰基和α-硝基酮的不对称转移氢化反应中产生出色的对映选择性。该催化剂可提供具有很高ee值的邻位取代的芳族醇。该二胺配体可直接用作手性配体。不必转化为相应的磺酰胺。
• Application of <i>N</i>-Acylbenzotriazoles in the Synthesis of 5-Substituted 2-Ethoxy-1,3,4-oxadiazoles as Building Blocks toward 3,5-Disubstituted 1,3,4-Oxadiazol-2(3<i>H</i>)-ones
  作者：Sirawit Wet-osot、Wong Phakhodee、Mookda Pattarawarapan

  DOI：10.1021/acs.joc.7b01863

  日期：2017.9.15

  N-acylation/dehydrative cyclization between ethyl carbazate and N-acylbenzotriazoles in the presence of Ph3P–I2 as a dehydrating agent. Subsequent treatment with a stoichiometric amount of alkyl halides (X = Cl, Br, I) enables a rapid access to a variety of 3,5-disubstituted 1,3,4-oxadiazol-2(3H)-ones in good to excellent yields.

  5-取代的2-乙氧基-1,3,4-恶二唑被方便地通过一釜连续制备Ñ酰化/脱水闭环之间肼基甲酸乙酯和Ñ -acylbenzotriazoles pH值的存在3 P-I 2作为脱水代理人。随后用化学计量的烷基卤化物（X = Cl，Br，I）处理，可以快速获得各种3,5-二取代的1,3,4-恶二唑-2（3 H）-良好至优异产量。
• Trichloroisocyanuric Acid Mediated High-Yielding Synthesis of N-Acylbenzotriazoles under Mild Reaction Conditions
  作者：Mala Singh、Anoop Singh、Nidhi Mishra、Anand Agrahari、Vinod Tiwari

  DOI：10.1055/s-0037-1611724

  日期：2019.5

  salient features of the developed reaction path include an economic, facile, base-free, and equally useful method in milligram to gram scale. N-Acylbenzotriazoles are achieved in good yields from the corresponding carboxylic acids by using only 0.35 equivalent of trichloroisocyanuric acid and 1.2 equivalents of PPh3. The salient features of the developed reaction path include an economic, facile, base-free

  这份手稿专门献给（后期）Alan R. Katritzky教授对苯并三唑化学的贡献。 抽象的 通过仅使用0.35当量的三氯异氰尿酸和1.2当量的PPh 3，由相应的羧酸以良好的产率获得N-酰基苯并三唑。发达的反应路径的显着特征包括一种经济，简便，无碱且在毫克到克范围内同样有用的方法。 通过仅使用0.35当量的三氯异氰尿酸和1.2当量的PPh 3，由相应的羧酸以良好的产率获得N-酰基苯并三唑。发达的反应路径的显着特征包括一种经济，简便，无碱且在毫克到克范围内同样有用的方法。