phenyl-thiocarbamic acid (S)-4-chlorophenyl ester | 64651-83-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenyl-thiocarbamic acid (S)-4-chlorophenyl ester
• 英文别名: N-phenylthiocarbamic acid S-4-chlorophenyl ester；phenyl-thiocarbamic acid S-4-chlorophenyl ester；S-(4-chlorophenyl)-N-phenyl thiocarbamate；S-(4-chlorophenyl) phenylcarbamothioate；S-(4-chlorophenyl) N-phenylcarbamothioate
• CAS: 64651-83-8
• 化学式: C₁₃H₁₀ClNOS
• 分子量: 263.748
• InChiKey: HFAKYDJGZZXQSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  phenyl-thiocarbamic acid (S)-4-chlorophenyl ester 在 高氯酸 、 thallium(III) nitrate 作用下， 以 1,4-二氧六环 为溶剂， 生成 苯胺
  参考文献：
  名称：

  Satchell, Derek P. N.; Satchell, Rosemary S.; Wassef, Wasfy N., Journal of the Chemical Society. Perkin transactions II, 1992, # 7, p. 1199 - 1202

  摘要：

  DOI：
• 作为产物：
  描述：

  chloro-thioformic acid (4-chloro-phenyl)ester 在 /BRN= 605631/ 作用下， 以 苯 为溶剂， 生成 phenyl-thiocarbamic acid (S)-4-chlorophenyl ester
  参考文献：
  名称：

  Litvinenko,L.M. et al., Journal of Organic Chemistry USSR (English Translation), 1977, vol. 13, p. 1532 - 1536

  摘要：

  DOI：

文献信息

• Synthesis of Thiocarbamates from Thiols and Isocyanates Under Catalyst- and Solvent-Free Conditions
  作者：Barahman Movassagh、Mohammad Soleiman-Beigi

  DOI：10.1007/s00706-007-0762-7

  日期：2008.2

  A simple and efficient procedure was developed for the synthesis of S -alkyl (aryl) thiocarbamates under solvent-free conditions without the use of a catalyst. The significant features of this protocol are (a) operational simplicity, (b) mild reaction conditions, (c) short reaction times, (d) solvent-free conditions, and (e) high product yields.

  开发了一种简单有效的方法，用于在无溶剂条件下不使用催化剂合成 S- 烷基（芳基）硫代氨基甲酸酯。该方案的显着特征是（a）操作简便，（b）反应条件温和，（c）反应时间短，（d）无溶剂条件和（e）产品收率高。
• Nucleophilic Substitution Reactions of Aryl <i>N</i>-Phenyl Thiocarbamates with Benzylamines in Acetonitrile
  作者：Hyuck Keun Oh、Jie Eun Park、Dae Dong Sung、Ikchoon Lee

  DOI：10.1021/jo049845+

  日期：2004.4.1

  reactions of esters. This large rate increase and the similar change in the aminolysis rates that are reported to occur from aryl ethyl carbonate (EtOC(O)OC6H4Z; 2a) to aryl ethylthiocarbonate (EtOC(O)SC6H4Z; 2b) lead us to conclude that the aminolysis of 3b proceeds by a concerted mechanism in contrast to a stepwise process for 3a. The negative ρXZ values (−0.63) and violation of the reactivity−selectivity

  研究了芳基N-苯硫代氨基甲酸酯（PhNHC（O）SC 6 H 4 Z; 3b）与苄胺（XC 6 H 4 CH 2 NH 2）在乙腈中的氨解反应。速率比芳基N-苯基氨基甲酸酯（PhNHC（O）OC 6 H 4 Z; 3a）的相应反应快得多。速率从3a增加到3b大于在酯的逐步氨解反应中用噻吩氧化物取代苯酚离去基团所期望的值。据报道，从碳酸芳基乙酯（EtOC（O）OC 6 H 4 Z; 2a）到硫代碳酸芳基乙酯（EtOC（O）SC 6 H 4 Z; 2b）发生的速率大幅度提高，氨解率也发生了类似的变化。导致我们得出结论，与3a的逐步过程相反，3b的氨解是通过协同机制进行的。负ρ XZ值（-0.63）和违反反应性选择性原则（RSP）都支持所提出的机制。大β X所获得的值（1.3-1.5）被认为是表示在过渡状态，这是与比较大的动力学同位素效应是一致的（在很大程度上键制作ķ ħ / ķ d观察到> 1
• One-pot synthesis of carbamates and thiocarbamates from Boc-protected amines
  作者：Hee-Kwon Kim、Anna Lee

  DOI：10.1016/j.tetlet.2016.09.038

  日期：2016.11

  A highly efficient one-pot procedure for the synthesis of carbamates and thiocarbamates has been described. In the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, the isocyanate intermediates were generated in situ for further reactions with alcohols and thiols to afford the desired carbamates and thiocarbamates in high yields.

  已经描述了用于合成氨基甲酸酯和硫代氨基甲酸酯的高效一锅法。在2-氯吡啶和三氟甲磺酰酐的存在下，原位生成异氰酸酯中间体，用于与醇和硫醇的进一步反应，以高收率提供所需的氨基甲酸酯和硫代氨基甲酸酯。
• Kinetics and mechanism of the anilinolysis of<i>S</i>-aryl<i>N</i>-arylthiocarbamates in acetonitrile
  作者：Dae Dong Sung、Hee Man Jang、Dae Il Jung、Ikchoon Lee

  DOI：10.1002/poc.1418

  日期：2008.11

  values that are consistent for a stepwise mechanism with rate-limiting formation of the zwitterionic tetrahedral intermediate. Signs of cross-interaction constants, ρXY (>0), ρXZ (>0) and ρYZ (<0), are all consistent with a stepwise mechanism. It is concluded that the change of the amine from benzylamines to anilines causes a shift of the aminolysis mechanism from a concerted to a stepwise process. Copyright

  研究了S-芳基N-芳基硫代氨基甲酸酯（YC 6 H 4 NH C（O）SC 6 H 4 Z，1）与苯胺在乙腈中的氨解反应。的反应速率更受亲核试剂比所述离去基团的nucleofugality的亲核性的影响，但反应物从给TS用于形成四面体中间体的在有效电荷的改变是离去基团在稍大（β ž从- 0.07至-0.14）比在亲核试剂（β X = 0.04-0.12）。布朗斯台德系数的大小在与限速地形成两性离子四面体中间体的逐步机理一致的值的范围内。交叉相互作用常数的迹象，ρ XY（> 0），ρ XZ（> 0）和ρ YZ（<0），都具有阶梯状机制是一致的。结论是，胺从苄胺变为苯胺导致氨解机理从协同过程转变为逐步过程。版权所有©2008 John Wiley＆Sons，Ltd.
• A Novel One-Pot Solvent-Free, Triethylamine-Assisted, Selenium-Catalyzed Synthesis of Thiocarbamates from Nitroarenes, Carbon Monoxide, and Thiols
  作者：Shiwei Lu、Xiaopeng Zhang

  DOI：10.1055/s-2005-869839

  日期：——

  A novel one-pot solvent-free synthesis of a series of thiocarbamates is reported. Nitroarenes, carbon monoxide, and thiols are the starting materials, with cheap element selenium as catalyst; this method offers a simple access to thiocarbamates mostly in moderate to good yields. The selenium catalyst can be easily recovered and recycled.

  报道了一种新颖的无溶剂一锅法合成一系列硫代氨基甲酸酯的方法。以硝基芳烃、一氧化碳和硫醇为原料，廉价元素硒为催化剂；该方法可便捷地合成硫代氨基甲酸酯，产率大多为中等到良好。硒催化剂易于回收再利用。