cyclohexyldithiocarbamic acid benzyl ester | 28249-18-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cyclohexyldithiocarbamic acid benzyl ester
• 英文别名: benzyl cyclohexylcarbamodithioate；benzyl N-cyclohexylcarbamodithioate
• CAS: 28249-18-5
• 化学式: C₁₄H₁₉NS₂
• 分子量: 265.444
• InChiKey: XIKVVQONOWCFKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环己胺 、 alkaline earth salt of/the/ methylsulfuric acid 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 34.0h， 生成 cyclohexyldithiocarbamic acid benzyl ester
  参考文献：
  名称：

  Benzotriazole-Assisted Thioacylation

  摘要：

  Benzotriazole reagents for thioacylation (RCSBt), thiocarbamoylation (RR'NCSBt), aryl/alkoxythioacylation (ROCSBt), and aryl/alkylthiothioacylation (RSCSBt) are synthesized, and their utility is assessed by syntheses of representative heteroaryl thioureas 3a-g, thioamides 15a-s, thionoesters 16a-h, thiocarbamates 17a-e, dithiocarbamates 18a-d, thiocarbonates 19a-c, and dithiocarbonates 20a-c.

  DOI：

  10.1021/jo050670t

文献信息

• An efficient synthesis of dithiocarbamates under ultrasound irradiation in water
  作者：Najmadin Azizi、Elahm Gholibeglo、Sanaz Dehghan Nayeri

  DOI：10.1007/s00706-011-0687-z

  日期：2012.8

  economic, and green method for the synthesis of dithiocarbamate derivatives in water. The one-pot, three-component condensation of primary and secondary amines with carbon disulfide and unsaturated carbonyl compounds or alkyl halides under ultrasonic irradiation was developed as a green and fast protocol for the rapid high-yielding preparation of dithiocarbamates in water. Graphical abstract

  摘要具有超声活化的多组分反应已被用作简单，快速，原子经济且绿色的方法，用于在水中合成二硫代氨基甲酸酯衍生物。伯胺和仲胺与二硫化碳和不饱和羰基化合物或烷基卤化物在超声波辐射下的一锅，三组分缩合反应是一种绿色快速的方法，用于在水中快速高产率地制备二硫代氨基甲酸酯。 图形概要
• Straightforward and Highly Efficient Catalyst-Free One-Pot Synthesis of Dithiocarbamates under Solvent-Free Conditions
  作者：Najmedin Azizi、Fezzeh Aryanasab、Mohammad R. Saidi

  DOI：10.1021/ol0620141

  日期：2006.11.9

  [Structure: see text] A highly efficient and simple synthesis of dithiocarbamates is possible based on the one-pot reaction of amines, CS2, and alkyl halides without using a catalyst under solvent-free conditions. The mild reaction conditions, high yields, and broad scope of the reaction illustrate the good synthetic utility of this method. The reaction is a highly atom-economic process for production

  [结构：见正文]基于胺，CS2和烷基卤化物的一锅反应，在无溶剂条件下无需使用催化剂，即可高效且简单地合成二硫代氨基甲酸酯。温和的反应条件，高收率和广泛的反应范围说明了该方法的良好合成实用性。该反应是生产S-烷基硫代氨基甲酸酯的高度原子经济的方法，可成功地大量用于制药或农业化学工业。
• <i>S</i>-alkyl Dithiocarbamates Synthesis through Electrochemical Multicomponent Reaction of Thiols, Hydrogen Sulfide, and Isocyanides
  作者：Xiaoying Liu、Tian-cheng Cai、Mengxue Zhu、Yuxuan Liu、Jingjing Xia、Junyan Xie、Lixin Wen、Qing-Wen Gui、Yulong Yin

  DOI：10.1021/acs.joc.3c01017

  日期：2023.9.1

  challenge. In this work, we have successfully developed a multicomponent reaction protocol to convert H2S into S-alkyl dithiocarbamates under constant current conditions. No additional oxidants nor additional catalysts are required, and due to mild conditions, the reactions display a broad substrate scope, including varieties of thiols or disulfides.

  二硫代氨基甲酸盐的合成在许多生物医学和农业化学应用中极其重要，特别是杀菌剂的开发，但仍然是一个巨大的挑战。在这项工作中，我们成功开发了一种多组分反应方案，可在恒流条件下将H 2 S转化为S-烷基二硫代氨基甲酸酯。不需要额外的氧化剂或额外的催化剂，并且由于条件温和，反应显示出广泛的底物范围，包括各种硫醇或二硫化物。
• Exploring the Structural Requirements for Inhibition of the Ubiquitin E3 Ligase Breast Cancer Associated Protein 2 (BCA2) as a Treatment for Breast Cancer
  作者：Ghali Brahemi、Fathima R. Kona、Annalisa Fiasella、Daniela Buac、Jitka Soukupová、Andrea Brancale、Angelika M. Burger、Andrew D. Westwell

  DOI：10.1021/jm901757t

  日期：2010.4.8

  The zinc-ejecting aldehyde dehydrogenase (A LDH) inhibitory drug disulfiram (DS F) was found to be a breast cancer-associated protein 2 (BCA2) inhibitor with potent antitumor activity. We herein describe our work in the synthesis and evaluation of new series of zinc-affinic molecules to explore the structural requirements for selective BCA2-inhibitory antitumor activity. An N(C=S)S-S motif was found to be required, based on selective activity in BCA2-expressing breast cancer cell lines and against recombinant BCA2 protein. Notably, the DSF analogs (3a and 3c) and dithio(peroxo)thioate compounds (5d and 5f) were found to have potent activity (submicromolar IC(50)) in BCA2 positive MCF-7 and T47D cells but were inactive (IC(50)> 10 mu M) in BCA2 negative M DA-MB-231 breast cancer cells and the normal breast epithelial cell line MCF10A. Testing in the isogenic BCA2 +ve M DA-MB-231/ER cell line restored antitumor activity for compounds that were inactive in the BCA2 -ve MDA-MB-231 cell line. In contrast, structurally related dithiocarbamates and benzisothiazolones (lacking the disulfide bond) were all inactive. Compounds 5d and 5f were additionally found to lack ALDH-inhibitory activity, suggestive of selective E3 ligase-inhibitory activity and worthy of further development.
• SILHANEK, J.;TREUTLEROVA, V.;ZBIROVSKY, M., SB. VSCHT PRAZE, 1982, 27, 103-111
  作者：SILHANEK, J.、TREUTLEROVA, V.、ZBIROVSKY, M.

  DOI：——

  日期：——