N-benzyl O-ethyl thiocarbamate | 55365-86-1

• 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: N-benzyl O-ethyl thiocarbamate
• 英文别名: benzylthiocarbamic acid O-ethyl ester；Thiokohlensaeure-O-aethylester-benzylamid；Benzyl-thiocarbamidsaeure-O-aethylester；O-ethyl N-benzylcarbamothioate
• CAS: 55365-86-1
• 化学式: C₁₀H₁₃NOS
• 分子量: 195.285
• InChiKey: DOQOZLJUQOFXET-UHFFFAOYSA-N

物化性质

• 保留指数：
  1687

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl O-ethyl thiocarbamate 以50%的产率得到
  参考文献：
  名称：

  HANEFELD W., J. LIEBIGS ANN. CHEM. , 1974, NO 12, 2015-2018

  摘要：

  DOI：
• 作为产物：
  描述：

  μ-disulfido-1,2-dithio-dicarbonic acid bis-benzylamide 在 sodium ethanolate 作用下， 生成 N-benzyl O-ethyl thiocarbamate
  参考文献：
  名称：

  Schneider; Clibbens; Huellweck, Chemische Berichte, 1914, vol. 47, p. 1255

  摘要：

  DOI：

文献信息

• Synthesis of Sulfonylisoureas via Sulfo-Click Reactions
  作者：Moritz Ottenbruch、Fabian Mohr、Stefan F. Kirsch

  DOI：10.1055/s-0039-1691505

  日期：2020.3

  The synthesis of sulfonylisoureas from thiocarbamates and sulfonyl azides via a new variant of the sulfo-click reaction is reported. Water was found to be the environmentally benign solvent of choice over various other solvents tested, and the use of any additives was not required to obtain complete conversion. The experimentally simple reaction­ tolerates a broad range of electron-donating and electron-withdrawing

  据报道，通过硫代点击反应的新变体，由硫代氨基甲酸酯和磺酰叠氮化物合成了磺酰脲类。已发现，与测试的其他各种溶剂相比，水是一种对环境无害的选择，并且不需要使用任何添加剂即可获得完全的转化率。实验上简单的反应可耐受连接在硫代氨基甲酸酯和磺酰叠氮化物上的广泛的供电子和吸电子取代基，如27种磺酰脲类的合成所示，其收率范围为34％至78％。
• Kinetics and Mechanism of the Aminolysis of S-Aryl O-Ethyl Dithiocarbonates in Acetonitrile
  作者：Hyuck Keun Oh、Ji Young Oh、Dae Dong Sung、Ikchoon Lee

  DOI：10.1135/cccc20042174

  日期：——

  The aminolysis of S-aryl O-ethyl dithiocarbonates with benzylamines are studied in acetonitrile at -25.0 °C. The β_X (β_nuc) values are in the range 0.67-0.77 with a negative cross-interaction constant, ρ_XZ = -0.24, which are interpreted to indicate a concerted mechanism. The kinetic isotope effects involving deuterated benzylamine nucleophiles (XC₆H₄CH₂ND₂) are large, k_H/k_D = 1.41-1.97, suggesting that the N-H(D) bond is partially broken in the transition state by forming a hydrogen-bonded four-center cyclic structure. The concerted mechanism is enforced by the strong push provided by the EtO group which enhances the nucleofugalities of both benzylamine and arenethiolate from the putative zwitterionic tetrahedral intermediate.

  在乙腈中以-25.0°C条件下研究了苯基乙基二硫代碳酸酯与苄胺的氨解反应。βX（βnuc）值在0.67-0.77范围内，具有负的交叉作用常数ρXZ = -0.24，这被解释为指示了一个协同机制。涉及氘代苄胺亲核试剂（XC6H4CH2ND2）的动力学同位素效应很大，kH/kD = 1.41-1.97，表明在过渡态中N-H(D)键部分断裂，形成一个氢键四中心环结构。协同机制由EtO基团提供的强推动力加强了苄胺和芳硫醇从假定的带电离子四面体中间体的亲核性。
• Niaziminin, a Thiocarbamate from the Leaves of<i>Moringa oleifera</i>, Holds a Strict Structural Requirement for Inhibition of Tumor-Promoter-Induced Epstein-Barr Virus Activation
  作者：Akira Murakami、Yumi Kitazono、Suratwadee Jiwajinda、Koichi Koshimizu、Hajime Ohigashi

  DOI：10.1055/s-2006-957442

  日期：1998.5

  Three known thiocarbamate (TC)- and isothiocyanate (ITC)-related compounds have been isolated from the leaves of Moringa oleifera, a traditional herb in southeast Asia, as inhibitors of tumor promoter teleocidin B-4-induced Epstein-Barr virus (EBV) activation in Raji cells. Interestingly, only niaziminin among 10 TCs including 8 synthetic ones showed considerable inhibition against EBV activation. The structure-activity relationships indicated that the presence of an acetoxy group at the 4′-position of niaziminin is important and indispensable for inhibition. On the other hand, among the ITC-related compounds, naturally occurring 4-[(4′-O-acetyl-α-L-rhamnosyloxy)benzyl]ITC and commercially available allyl- and benzyl-ITC significantly inhibited activation, suggesting that the isothiocyano group is a critical structural factor for activity.

  从东南亚传统草药辣木的叶子中分离出三种已知的硫代氨基甲酸盐（TC）和异硫氰酸盐（ITC）相关化合物，它们被鉴定为肿瘤促进剂大田软海绵素B-4诱导的Raji细胞中的爱泼斯坦-巴尔病毒（EBV）激活的抑制剂。有趣的是，在包括8种合成化合物在内的10种TC中，只有niaziminin表现出对EBV激活的显著抑制作用。结构-活性关系研究表明，niaziminin在4′-位置上的乙酰氧基对于抑制作用至关重要且不可或缺。另一方面，在ITC相关化合物中，天然存在的4-[(4′-O-乙酰基-α-L-鼠李糖基氧)苄基]ITC以及市售的烯丙基-和苄基-ITC均显著抑制激活，表明异硫氰酸根基团是活性中的关键结构因素。
• Identification of New, Odor-Active Thiocarbamates in Cress Extracts and Structure−Activity Studies on Synthesized Homologues
  作者：Katharina Breme、Xavier Fernandez、Uwe J. Meierhenrich、Hugues Brevard、Daniel Joulain

  DOI：10.1021/jf062856e

  日期：2007.3.1

  botanical order Brassicales and produces glucosinolates, which are important precursors of nitrogen- and sulfur-containing compounds. Those compounds often present low perception thresholds and various olfactive notes and are thus of interest to the flavor and fragrance chemistry. When the study of organonitrogen and organosulfur compounds is undertaken, Brassicale extracts are one of the matrices of choice

  在水芹提取物中鉴定出新的，有气味的含氮和硫的化合物。水芹属于植物十字花科，并产生芥子油苷，芥子油苷是含氮和硫的化合物的重要前体。这些化合物通常呈现出低的感知阈值和各种嗅觉，因此对于风味和香气化学是令人感兴趣的。在进行有机氮和有机硫化合物的研究时，十字花科植物提取物是选择的基质之一。通过分析（GC-MS，GC-FPD）和化学（分馏）方法研究了水芹提取物，以鉴定出新的有趣的香气化合物。在水芹提取物中发现了两个从未报道过的化合物，其中既含氮又含硫：N-苄基O-乙基硫代氨基甲酸酯和N-苯乙基O-乙基硫代氨基甲酸酯。这两个分子具有感官上的意义，合成了它们的同系物，并进行了感官测试（静态和GC嗅探）。它们的气味从大蒜和洋葱到绿色，蘑菇状和水芹状，再到新鲜的，留兰香状。本文介绍了一系列O-烷基硫代氨基甲酸酯的来源，化学合成和感官特性。
• Effect of successive increase in alcohol chains on reaction with isocyanates and isothiocyanates
  作者：Shahnaz Perveen、Arfa Yasmin、Khalid Mohammed Khan

  DOI：10.1080/14786410802270738

  日期：2010.1.10

  The reaction of isocyanates and isothiocyanates with long-chain alcohols, e.g. n-hexanol, n-heptanol and n-octanol, exclusively gave N-aryl-O-alkyl carbamates, while N-aryl-O-alkyl carbamates were formed along with symmetrical 1,3-disubstituted ureas and thioureas when the same reactions were carried out with small-chain alcohols at room temperature without using any solvent.

  异氰酸酯和异硫氰酸酯与长链醇，例如将反应Ñ己醇，Ñ庚醇和Ñ辛醇，只给Ñ -芳基- ø -烷基氨基甲酸盐，而Ñ -芳基- ö烷基用对称沿形成氨基甲酸酯当在不使用任何溶剂的情况下与小链醇在室温下进行相同的反应时，1,3-二取代的脲和硫脲。