4-methylbenzyl pyrrolidine-1-carbodithioate | 1220849-84-2

• 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: 4-methylbenzyl pyrrolidine-1-carbodithioate
• 英文别名: (4-Methylphenyl)methyl pyrrolidine-1-carbodithioate
• CAS: 1220849-84-2
• 化学式: C₁₃H₁₇NS₂
• 分子量: 251.417
• InChiKey: HOAGYCWEONQYNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (4-甲基苯基)甲醇 、 sodium pyrrolidine-N-carbodithioate 在 Cu nanoparticles on hydroxyapatite 作用下， 以 甲苯 为溶剂， 以85 %的产率得到4-methylbenzyl pyrrolidine-1-carbodithioate
  参考文献：
  名称：

  使用醇作为烷基化剂通过借氢反应策略对二硫代氨基甲酸酯进行 S-烷基化

  摘要：

  在此，我们报告了一种操作简单、环境友好且可扩展的方法，通过使用羟基磷灰石负载的铜纳米催化剂催化醇和二硫代氨基甲酸根阴离子之间的借氢反应来合成S-苄基/烷基二硫代氨基甲酸酯。该策略具有广泛的底物范围，并使用廉价且容易获得的醇作为起始材料提供高产率的产品。该催化剂通过简单直接的方法制备，并通过多种分析技术进行分析，例如FESEM、HR-TEM、BET、XRD、EDS和XPS，证明了Cu纳米颗粒在零氧化态下锚定在羟基磷灰石上。

  DOI：

  10.1039/d3ob00958k

文献信息

• Variable non-covalent interactions in the crystals of a series of 4-Y-benzyl pyrrolidine-1-carbodithioates: Y = Cl, Br, I, Me and NO₂
  作者：Chien Ing Yeo、Huey Chong Kwong、Sang Loon Tan、Edward R. T. Tiekink

  DOI：10.1039/d4ce00158c

  日期：——

  into layers through phenyl-C–H⋯S(thione), methylene-C–H⋯π(phenyl) and off-set phenyl-π⋯π(phenyl) stacking. Layers are also evident in the methyl species, 4, with directional pyrrolidine-C–H⋯π(phenyl) and π(phenyl)⋯π(phenyl) interactions apparent between molecules. In the three-dimensional architecture of nitro derivative 5, methylene-C–H⋯π(phenyl) and long phenyl-C–H⋯O(nitro) interactions are discerned

  吡咯烷二硫代氨基甲酸酯的一系列五种S-苄酯，仅在苄基4位的取代基不同，即(CH 2 CH 2 ) 2 NC( S)SCH 2 C 6 H 4 -4-Y Y = Cl、Br、I、Me 和 NO 2 ( 1–5 )，已通过晶体学和计算化学技术进行了研究，包括计算赫什菲尔德表面的分析和相互作用能的计算。分子构象的显着差异，例如C-S（硫醚）-C（亚甲基）-C 扭转角几乎 90° 的差异，与通过不受限制的几何优化计算揭示的堆积效应有关。远程取代基 Y 对分子堆积的影响至关重要，阐明了四种不同的堆积模式。在氯衍生物中，1，Cl⋯Cl 接触具有 C-H⋯π 相互作用的层之间的特征。在每个同晶溴 ( 2 ) 和碘 ( 3 ) 衍生物中，在线性超分子链中检测到 X⋯S 卤素键，这些超分子链通过苯基-C–H⋯S(硫酮)、亚甲基-C–H⋯ 组装成层。 π(苯基) 和偏移苯基-π⋯π(苯基) 堆积。甲基物种4中
• Direct conversion of methylarenes into dithiocarbamates, thioamides and benzyl esters
  作者：Tirumaleswararao Guntreddi、Rajeshwer Vanjari、Krishna Nand Singh

  DOI：10.1016/j.tet.2014.04.041

  日期：2014.6

  A new strategy for the synthesis of a variety of dithiocarbamates and thioamides has been developed employing inexpensive and readily available methylarenes under metal-free and solvent-free conditions. The approach offers a one-pot procedure and has also been extended to the synthesis of a diverse range of benzyl esters. (C) 2014 Elsevier Ltd. All rights reserved.
• 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.
• <i>S</i>-Alkylation of dithiocarbamates <i>via</i> a hydrogen borrowing reaction strategy using alcohols as alkylating agents
  作者：Hima P、Spandan Hati、Raju Dey

  DOI：10.1039/d3ob00958k

  日期：——

  synthesis of S-benzyl/alkyl dithiocarbamates via a hydrogen borrowing reaction between alcohols and dithiocarbamate anions catalyzed using a hydroxyapatite-supported copper nano-catalyst. This strategy has a broad substrate scope and offers high yields of products using inexpensive and readily available alcohols as starting materials. The catalyst was prepared by easy and straightforward methods and

  在此，我们报告了一种操作简单、环境友好且可扩展的方法，通过使用羟基磷灰石负载的铜纳米催化剂催化醇和二硫代氨基甲酸根阴离子之间的借氢反应来合成S-苄基/烷基二硫代氨基甲酸酯。该策略具有广泛的底物范围，并使用廉价且容易获得的醇作为起始材料提供高产率的产品。该催化剂通过简单直接的方法制备，并通过多种分析技术进行分析，例如FESEM、HR-TEM、BET、XRD、EDS和XPS，证明了Cu纳米颗粒在零氧化态下锚定在羟基磷灰石上。