butyl N,N-diethyldithiocarbamate | 19833-74-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 二硫代氨基甲酸及其衍生物
• 英文名称: butyl N,N-diethyldithiocarbamate
• 英文别名: butyl diethylcarbamodithioate；N,N-Diethyl-dithiocarbaminsaeure-butylester；butyl N,N-diethylcarbamodithioate
• CAS: 19833-74-0
• 化学式: C₉H₁₉NS₂
• mdl: MFCD25960678
• 分子量: 205.389
• InChiKey: YHHDKISPKFKNSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  60.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二硫化四乙基秋兰姆 、 氯丁烷 在 caesium carbonate 作用下， 以 氘代二甲亚砜 为溶剂， 反应 12.0h， 以65%的产率得到butyl N,N-diethyldithiocarbamate
  参考文献：
  名称：

  使用秋兰姆二硫化物试剂合成烷基二硫代氨基甲酸酯：形成无金属的C（sp 3）-S键

  摘要：

  已经实现了用于合成S-烷基二硫代氨基甲酸酯的有效且环境友好的方案。通过使四烷基秋兰姆二硫化物与烷基卤化物反应，可以良好至极好的收率获得所需的产物。该方法具有高效，无过渡金属，高收率和易操作的特点，说明了其实用合成价值，可方便地制备一些潜在的生物活性分子。

  DOI：

  10.1016/j.tetlet.2019.01.044

文献信息

• 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。
• 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.
• Smith,T.D., Journal of the Chemical Society, 1961, p. 3164 - 3165
  作者：Smith,T.D.

  DOI：——

  日期：——
• Syntheses of Organic N,N-Dialkyldithiocarbamates or Organic Thiocyanates from Organozincs and Corresponding Thio-Anions via the Inversion of Electronic Reactivity of the Anions with NCS-Oxidation
  作者：Kentaro Takagi、Hideaki Takachi、Ken Sasaki

  DOI：10.1021/jo00125a047

  日期：1995.10

  Novel displacement of metal ions from organometallic compounds with nucleophilic reagents was achieved in the reaction between organozinc compounds and N,N-dialkyldithiocarbamate ions (N,N-DAD(-)) or thiocyanate ion by the assistance of NCS, whereby alkyl or aryl N,N-DAD or alkyl, alkenyl, alkynyl, aryl, or heteroaryl thiocyanates were obtained in moderate to excellent yields as the result of novel bond construction between carbon fragments from organozinc compounds and thio-anions.
• HORI, YUJI;MARUYAMA, RYOICHI;MOTOKAWA, HIROSHI;TANIGUCHI, HIROSHI, CHEM. EXPRESS, 3,(1988) N, C. 411-414
  作者：HORI, YUJI、MARUYAMA, RYOICHI、MOTOKAWA, HIROSHI、TANIGUCHI, HIROSHI

  DOI：——

  日期：——