[(4R)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanylidene]hydrazine | 73509-03-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(4R)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanylidene]hydrazine
• 英文别名: (2,2,4-trimethyl-3-bicyclo[2.2.1]heptanylidene)hydrazine；(1R)-(-)-Fenchone hydrazone；(1R)-fenchone hydrazone；(-)-fenchylhydrazone；fenchone hydrazone
• CAS: 73509-03-2；87900-48-9
• 化学式: C₁₀H₁₈N₂
• 分子量: 166.266
• InChiKey: PAIGSTUXPRTCJO-OIBJUYFYSA-N

物化性质

• 沸点：
  244.8±23.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  38.38
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  [(4R)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanylidene]hydrazine 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 methyl 1,3,3-trimethyl-5'-(4-nitrophenyl)-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-[1,3,4]oxadiazole]-3'-carboxylate
  参考文献：
  名称：

  樟脑和小茴香酮基螺环 1,3,4-恶二唑啉的简易立体选择性合成和结构研究

  摘要：

  首次开发了一种有效的合成螺环樟脑和小茴香酮基 1,3,4-恶二唑啉的方法。研究了萜烯支架对反应立体选择性的影响。所提出的方法可以以立体选择性和良好的产率获得具有广泛结构多样性的螺环产物。

  DOI：

  10.1002/ejoc.202300811
• 作为产物：
  描述：

  (-)-fenchone 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 [(4R)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanylidene]hydrazine
  参考文献：
  名称：

  樟脑和小茴香酮基螺环 1,3,4-恶二唑啉的简易立体选择性合成和结构研究

  摘要：

  首次开发了一种有效的合成螺环樟脑和小茴香酮基 1,3,4-恶二唑啉的方法。研究了萜烯支架对反应立体选择性的影响。所提出的方法可以以立体选择性和良好的产率获得具有广泛结构多样性的螺环产物。

  DOI：

  10.1002/ejoc.202300811

文献信息

• Synthesis and Antiviral Activity of N-Heterocyclic Hydrazine Derivatives of Camphor and Fenchone
  作者：Kseniya S. Kovaleva、Olga I. Yarovaya、Yurii V. Gatilov、Aleksander V. Slita、Yana L. Esaulkova、Vladimir V. Zarubaev、Nadezhda B. Rudometova、Nadezhda S. Shcherbakova、Dmitrii N. Shcherbakov、Nariman F. Salakhutdinov

  DOI：10.1007/s10593-021-02923-5

  日期：2021.4

  heterocyclic derivatives was investigated. It was shown that the reaction of hydrazones with 1,2-ethanedithiol in the presence of formaldehyde with the addition of 5% Sm(NO3)3·6H2O leads to the formation of compounds containing the 1,5,3-dithiazepane fragment. The method developed by us offers the advantage of the use of commercially available reagents and good yields in the synthesis of hydrazone

  研究了（+）-樟脑和（-）-ench酮的hydr的伯氨基与二卤代烷烃的烷基化反应，从而产生了新型的含氮杂环衍生物。结果表明，与1,2-乙二硫醇在甲醛存在下，添加5％Sm（NO 3）3 ·6H 2 O的反应导致形成含有1,5,3-二硫杂ze烷的化合物分段。我们开发的方法具有在commercially杂环衍生物的合成中使用可商购试剂的优点和高收率的优点。抗病毒活性的研究表明，基于樟脑的N-杂环化合物可被视为具有抗A型流感活性的有前途的药物。
• Preparation of functionalized tertiary thiols and nitrosothiols
  作者：Chia-En Lin、Stewart K. Richardson、Weiheng Wang、Tiansheng Wang、David S. Garvey

  DOI：10.1016/j.tet.2006.06.019

  日期：2006.8

  The development and preparation of five series of tertiary thiols and nitrosothiols as nitric oxide releasing molecules functionalized with acid, alcohol, or amine groups for future conjugation are reported.

  据报道，开发并制备了五系列叔硫醇和亚硝基硫醇，它们是一氧化氮释放分子，可被酸，醇或胺基官能化，以用于将来的缀合。
• Design, Synthesis, and Biological Evaluation of (+)‐Camphor‐ and (−)‐Fenchone‐Based Derivatives as Potent Orthopoxvirus Inhibitors
  作者：Anastasiya S. Sokolova、Kseniya S. Kovaleva、Sergey O. Kuranov、Nikolay I. Bormotov、Sophia S. Borisevich、Anastasiya A. Zhukovets、Olga I. Yarovaya、Olga A. Serova、Maxim B. Nawrozkij、Andrey A. Vernigora、Andrey V. Davidenko、Eduard M. Khamitov、Roman Y. Peshkov、Larisa N. Shishkina、Rinat A. Maksuytov、Nariman F. Salakhutdinov

  DOI：10.1002/cmdc.202100771

  日期：2022.6.20

  urgent that novel compounds against OPXV be developed. This study reports on the synthesis of a library of monoterpenoid derivatives. The synthesized compounds were tested against vaccinia virus, cowpox, and ectromelia virus. The time-of-addition assay and molecular docking study were performed to identify a possible biological target.

  随着正痘病毒 (OPXVs) 对人类健康构成日益严重的威胁，迫切需要开发针对 OPXV 的新型化合物。本研究报告了单萜衍生物库的合成。对合成的化合物进行了针对牛痘病毒、牛痘和雀斑病毒的测试。进行添加时间测定和分子对接研究以确定可能的生物靶标。
• Synthesis of conjugates of (aR,7S)-colchicine with monoterpenoids and investigation of their biological activity
  作者：E. S. Shchegravina、S. D. Usova、D. S. Baev、E. S. Mozhaitsev、D. N. Shcherbakov、S. V. Belenkaya、E. A. Volosnikova、V. Yu. Chirkova、E. A. Sharlaeva、E. V. Svirshchevskaya、I. P. Fonareva、A. R. Sitdikova、N. F. Salakhutdinov、O. I. Yarovaya、A. Yu. Fedorov

  DOI：10.1007/s11172-023-3730-4

  日期：2023.1

  Conjugates of the natural alkaloid (aR,7S)-colchicine with bicyclic monoterpenoids and their derivatives were synthesized for the first time. Molecular docking of the synthesized agents in the active site of the main viral protease of the SARS-CoV-2 virus was carried out. The cytotoxic properties of the agents against different cell lines and the ability to inhibit the main viral protease 3CLPro were

  首次合成了天然生物碱(aR,7S)-秋水仙碱与双环单萜及其衍生物的缀合物。对 SARS-CoV-2 病毒主要病毒蛋白酶活性位点的合成药物进行了分子对接。研究了这些药物针对不同细胞系的细胞毒性特性以及抑制主要病毒蛋白酶 3CLPro 的能力。
• Synthesis of some fenchyl-substituted alkenes and enol-ethers containing 3-oxyphenyl substituents by the Barton-Kellogg reaction
  作者：Luiz Francisco M. L. Ciscato、Erick L. Bastos、Fernando H. Bartoloni、Wolfgang Günther、Dieter Weiss、Rainer Beckert、Wilhelm Josef Baader

  DOI：10.1590/s0103-50532010001000014

  日期：——

  The synthesis of one fenchyl-substituted alkene and two enol-ethers, containing 3-oxyphenyl substituents by the Barton-Kellogg reaction is described. The tri-substituted aromatic fenchyl-alkene 1a was prepared in 53% yield from thiofenchone and a diazoanisole; whereas enol-ethers 1b and 1c were obtained (95 and 75% yield, respectively) using an inverse approach based on diazofenchone and aromatic thionoesters. A mixture of Z and E isomers was obtained in all cases; isomer attribution and quantification has been carried out by analysis of NMR spectroscopic data assisted by theoretical calculations (E/Z ratio: 1a = 0.72, 1b = 2.2, 1c = 1.8). Reaction proceeds with low stereoselectivity leading to the preferential formation of diastereoisomeric olefins and enol-ethers where the aromatic substituent resides at the side of the two fenchyl methyl groups.