1-cyclohexyl-5-cyclohexylaminotetrazole | 73565-25-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-cyclohexyl-5-cyclohexylaminotetrazole
• 英文别名: N,1-dicyclohexyl-1H-tetrazol-5-amine；cyclohexyl-(1-cyclohexyl-1H-tetrazol-5-yl)-amine；N,1-dicyclohexyltetrazol-5-amine
• CAS: 73565-25-0
• 化学式: C₁₃H₂₃N₅
• 分子量: 249.359
• InChiKey: OUHRGNZCIPEWCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N,N'-二环己基碳二亚胺 在 叠氮基三甲基硅烷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-cyclohexyl-5-cyclohexylaminotetrazole
  参考文献：
  名称：

  异氰化物的选择性金催化氰胺和1取代的1H-替硝唑-5-胺的合成

  摘要：

  新发现的金催化的异氰化物与由三甲基甲硅烷基叠氮化物和甲醇（或由NaN 3 / AcOH产生）就地生成的氢氰酸反应，可生成氰胺或1取代的1 H-四唑-5-胺，具体取决于可用HN量3。该反应选择性地进行，并且两种产物的收率通常都很高，因此特别方便地获得了广泛的取代1 H-四唑-5-胺，而这些胺否则很难获得。

  DOI：

  10.1002/chem.201803252

文献信息

• Construction of 5-Aminotetrazoles via in Situ Generation of Carbodiimidium Ions from Ketones Promoted by TMSN₃/TfOH
  作者：Phongprapan Nimnual、Jumreang Tummatorn、Bundet Boekfa、Charnsak Thongsornkleeb、Somsak Ruchirawat、Pawida Piyachat、Kunlayanee Punjajom

  DOI：10.1021/acs.joc.9b00555

  日期：2019.5.3

  5-aminotetrazoles has been developed by employing simple ketones as substrates. This methodology involved the N2-extrusion/aryl migration of azido complexes as the key step for the in situ generation of carbodiimidium ion, which could further react with hydrazoic acid and cyclize intramolecularly to provide 5-aminotetrazoles in good to excellent yields. In addition, the regioselectivity of the reaction was studied

  通过使用简单的酮作为底物，已经开发了用于合成5-氨基四唑的新颖的合成方法。该方法涉及叠氮基络合物的N 2-挤出/芳基迁移，这是原位生成碳二亚胺离子的关键步骤，该碳二亚胺离子可进一步与酸反应并分子内环化，从而以优异的产率获得5-氨基四唑。另外，通过密度泛函理论计算研究了反应的区域选择性并使其合理化。
• An expedient route to the azoles through oxidative desulfurization using iodine reagent
  作者：Nikhil C. Jadhav、Prashant B. Jagadhane、Kavitkumar N. Patel、Vikas N. Telvekar

  DOI：10.1016/j.tetlet.2012.10.114

  日期：2013.1

  A novel and expedient regioselective method for the synthesis of 5-aminotetrazoles and 3-amino-1,2,4-triazoles through oxidative desulfurization of corresponding 1,3-disubstituted thioureas has been discovered and optimized for the process conditions. The process is broadly applicable to structurally diverse 1,3-disubstituted thioureas. (C) 2012 Elsevier Ltd. All rights reserved.
• <i>o</i>-Iodoxybenzoic Acid Mediated Oxidative Desulfurization Initiated Domino Reactions for Synthesis of Azoles
  作者：Pramod S. Chaudhari、Sagar P. Pathare、Krishnacharaya G. Akamanchi

  DOI：10.1021/jo2025509

  日期：2012.4.20

  A systematic exploration of thiophilic ability of o-iodoxybenzoic acid (IBX) for oxidative desulfurization to trigger domino reactions leading to new methodologies for synthesis of different azoles is described. A variety of highly substituted oxadiazoles, thiadiazoles, triazoles, and tetrazoles have been successfully synthesized in good to excellent yields, starting from readily accessible thiosemicarbazides, bis-diarylthiourea, 1,3-disubtituted thiourea, and thioamides.
• Reactions of trimethylsilyl azide with heterocumulenes
  作者：Otohiko Tsuge、Satoshi Urano、Koji Oe

  DOI：10.1021/jo01313a021

  日期：1980.12
• 1-Cyclohexyl-5-cyclohexylaminotetrazole
  作者：L. Govindasamy、S. Shanmuga Sundara Raj、D. Velmurugan、H.-K. Fun

  DOI：10.1107/s0108270198012888

  日期：1999.3.15

  The title compound, C13H23N5, consists of a planar tetrazole moiety and two cyclohexane rings substituted equatorially. Both cyclohexane rings adopt the chair conformation. The two cyclohexane rings are inclined to the mean plane of the tetrazole ring at 52.9(1) and 70.1(1)degrees and are at an angle of 74.5(1)degrees with each other. N-H ... N and C-H ... N hydrogen bonds join the molecules in chains running along the a axis.