(+/-)-2-(1,2,3-benzotriazol-1-yl)cyclohexanone

• 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: (+/-)-2-(1,2,3-benzotriazol-1-yl)cyclohexanone
• 英文别名: rac-2-(1H-benzo[d][1,2,3]triazol-1-yl)cyclohexanone；2-(1H-benzo[d][1,2,3]triazol-1-yl)cyclohexanone；2-(Benzotriazolyl)cyclohexanone；2-(benzotriazol-1-yl)cyclohexan-1-one
• 化学式: C₁₂H₁₃N₃O
• 分子量: 215.255
• InChiKey: SZAFJYWJUNIETJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  (+/-)-2-(1,2,3-benzotriazol-1-yl)cyclohexanone 在 甲酸 、 N-[(1R,2R)-1,2-diphenyl-2-(3-phenylpropylamino)ethyl]-4-methylbenzene sulfonamide ammonium chloride ruthenium 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以88.1%的产率得到
  参考文献：
  名称：

  钌催化的不对称转移加氢动力学驱动非对映和对映选择性合成顺式-β-杂芳基氨基环烷醇

  摘要：

  已证明束缚的Ru-TsDPEN催化剂可用于rac -α-杂芳基氨基环烷酮的不对称转移加氢，以通过动态动力学拆分构建具有两个连续手性中心的生物学上重要的顺式-β-杂芳基氨基环烷醇。所述（R，R）-Teth-TsDPEN-Ru-Ru催化的转化是在温和条件下使用甲酸/三乙胺作为氢源进行的，具有非对映和对映选择性优异。此外，该方法学已被用于抗霉菌剂和手性离子液体的合成。

  DOI：

  10.1021/acs.orglett.6b03334
• 作为产物：
  描述：

  1-(苯并三唑-1-基甲基)苯并三唑 在 正丁基锂 、 zinc dibromide 作用下， 以 四氢呋喃 、 正己烷 、 1,1,2,2-四氯乙烷 为溶剂， 反应 7.0h， 生成 (+/-)-2-(1,2,3-benzotriazol-1-yl)cyclohexanone
  参考文献：
  名称：

  General and Efficient Insertion of Carbons Carrying Benzotriazole

  摘要：

  Anions formed from the lithiation of 1-(1-benzotriazolylalkyl)benzotriazoles (1, 6) and 1-(1-methylthioalkyl)benzotriazoles (10 and 10a) with n-BuLi underwent additions to cyclic and acyclic ketones giving intermediates 3a-f, 7b-f, and 11b-d, respectively, in excellent yields. Thermal rearrangements of intermediates 3a,b,d-f and 7b-d,f in the presence of zinc bromide provided one-carbon chain-extended or ring-expanded cc-benzotriazolyl ketones 4a,b,d-f and 8b-d,f in moderate yields with excellent regioselectivity. By contrast, intermediates 11b-d on treatment with zinc bromide loose a molecule of benzotriazole followed by intramolecular cyclization of the resulting intermediates 12b-d to provide the 2,3- and 1,2,3-substituted indenes 13b-d in good yields.

  DOI：

  10.1021/jo035098p

文献信息

• Acid-Mediated Denitrogenation/Rearrangement/Coupling of ­Benzyl Azides with Triazolyl-Substituted Cycloalkanones
  作者：Ying Fu、Zhengyin Du、Yang Che、Rui Wang

  DOI：10.1055/s-0037-1610747

  日期：2020.3

  Organic molecules containing α-triazolyl or β-amino cyclic ketone fragments have been individually proven to show good bioactivities and to be useful in asymmetric and pharmaceutical syntheses. A triflic acid-promoted simple and efficient method for the synthesis of unsymmetrical α-triazolyl-α′-(aminomethyl)cycloalkanones from benzyl azides and α-triazolylcycloalkanones has been developed. A series

  含有 α-三唑基或 β-氨基环酮片段的有机分子已被单独证明显示出良好的生物活性，可用于不对称和药物合成。已经开发了一种三氟甲磺酸促进的简单有效的方法，用于从苄基叠氮化物和 α-三唑基环烷酮合成不对称 α-三唑基-α'-（氨甲基）环烷酮。以高顺式非对映选择性和高达 82% 的产率获得了一系列不对称的 α,α'-二取代环烷酮。对反应机理的检查表明，苄基叠氮化物通过环酮的烯醇形式进行质子化、氮消除、重排和亲电攻击。
• Iodine-induced regioselective direct alkylation of azoles via in situ formed alkyliodide
  作者：Wenlin Chen、Rulong Yan、Dong Tang、Shuaibo Guo、Xu Meng、Baohua Chen

  DOI：10.1016/j.tet.2012.07.008

  日期：2012.9

  We have developed an efficient, metal-free, convenient and relatively cheap method for iodine-induced direct alkylation of azoles via in situ formed alkyliodide. A series of heterocyclic derivatives are readily prepared under mild conditions in moderate to good yields and high regioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.
• IMIDAZOLES AS HISTONE DEMETHYLASE INHIBITORS
  申请人：Istituto Europeo di Oncologia S.r.l.

  公开号：EP3458460B1

  公开（公告）日：2020-12-09
• General and Efficient Insertion of Carbons Carrying Benzotriazole
  作者：Alan R. Katritzky、Sergey Bobrov、Kostyantyn Kirichenko、Yu Ji

  DOI：10.1021/jo035098p

  日期：2004.1.1

  Anions formed from the lithiation of 1-(1-benzotriazolylalkyl)benzotriazoles (1, 6) and 1-(1-methylthioalkyl)benzotriazoles (10 and 10a) with n-BuLi underwent additions to cyclic and acyclic ketones giving intermediates 3a-f, 7b-f, and 11b-d, respectively, in excellent yields. Thermal rearrangements of intermediates 3a,b,d-f and 7b-d,f in the presence of zinc bromide provided one-carbon chain-extended or ring-expanded cc-benzotriazolyl ketones 4a,b,d-f and 8b-d,f in moderate yields with excellent regioselectivity. By contrast, intermediates 11b-d on treatment with zinc bromide loose a molecule of benzotriazole followed by intramolecular cyclization of the resulting intermediates 12b-d to provide the 2,3- and 1,2,3-substituted indenes 13b-d in good yields.
• Kinetic Resolution Driven Diastereo- and Enantioselective Synthesis of <i>cis</i>-β-Heteroaryl Amino Cycloalkanols by Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation
  作者：Vijyesh K. Vyas、Bhalchandra M. Bhanage

  DOI：10.1021/acs.orglett.6b03334

  日期：2016.12.16

  been demonstrated for the asymmetric transfer hydrogenation of rac-α-heteroaryl amino cycloalkanones to construct biologically important cis-β-heteroaryl amino cycloalkanols with two contiguous chiral centers via dynamic kinetic resolution. The stated (R,R)-Teth-TsDPEN-Ru-catalyzed transformation is carried out under mild conditions using formic acid/triethylamine as a hydrogen source with excellent diastereo-

  已证明束缚的Ru-TsDPEN催化剂可用于rac -α-杂芳基氨基环烷酮的不对称转移加氢，以通过动态动力学拆分构建具有两个连续手性中心的生物学上重要的顺式-β-杂芳基氨基环烷醇。所述（R，R）-Teth-TsDPEN-Ru-Ru催化的转化是在温和条件下使用甲酸/三乙胺作为氢源进行的，具有非对映和对映选择性优异。此外，该方法学已被用于抗霉菌剂和手性离子液体的合成。