phenyl (4-tolylsulfonyl)carbamate | 18303-09-8

• 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: phenyl (4-tolylsulfonyl)carbamate
• 英文别名: phenyl N-(4-methylphenyl)sulfonylcarbamate
• CAS: 18303-09-8
• 化学式: C₁₄H₁₃NO₄S
• 分子量: 291.328
• InChiKey: DHQGWJSFNZWXBH-UHFFFAOYSA-N

物化性质

• 熔点：
  117 °C
• 沸点：
  130-135 °C(Press: 8 Torr)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氨基-5-溴噻唑 、 phenyl (4-tolylsulfonyl)carbamate 在 甲烷磺酸 作用下， 生成 N-[(5-bromo-1,3-thiazol-2-yl)carbamoyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Sulfonylureido thiazoles as fructose-1,6-bisphosphatase inhibitors for the treatment of Type-2 diabetes

  摘要：

  Sulfonylureido thiazoles were identified from a HTS campaign and optimized through a combination of structure-activity studies, X-ray crystallography and molecular modeling to yield potent inhibitors of fructose-1,6-bisphosphatase. Compound 12 showed favorable ADME properties, for example, F=70%, and a robust 32% glucose reduction in the acute db/db mouse model for Type-2 diabetes.

  DOI：

  10.1016/j.bmcl.2009.11.093
• 作为产物：
  描述：

  对甲基苯磺酰异氰酸酯 、 苯酚 以 二氯甲烷 为溶剂， 以85 %的产率得到phenyl (4-tolylsulfonyl)carbamate
  参考文献：
  名称：

  自促进 N-糖基化：扩展底物范围和取代基效应

  摘要：

  氨基酸侧链已在没有催化剂或添加剂帮助的情况下被功能化和糖基化。发现解除武装的糖基供体可以有效地反应，过量的糖基受体以及三氯乙酰胺可以通过水处理有效地去除。通过构建哈米特图研究了取代基对自促进糖基化的影响。

  DOI：

  10.1002/ejoc.202300213

文献信息

• Novel condensation polymers from N, N*-disubstituted disulfonamides
  申请人：Pews Garth R.

  公开号：US20060128924A1

  公开（公告）日：2006-06-15

  The present invention relates to novel condensation polymers where N,N*-disubstituted disulfonamides are copolymerized with an organic acid dihalide such as dicarboxylic acid dichlorides, disulfonic acid dichlorides, bis chloroformates, diphosphoryl acid dichlorides, diphosphonyl acid dichlorides, or phosgene or with diisocyanates. The polymers obtained are thermoplastic and useful in molding and extrusion application.

  本发明涉及新型缩聚聚合物，其中N，N* -二取代二磺酰胺与有机酸二卤代物（如二羧酸二氯化物，二磺酸二氯化物，双氯甲酸酯，二磷酸二氯化物，二膦酸二氯化物或光气）或二异氰酸酯共聚。所得到的聚合物是热塑性的，可用于模塑和挤出应用。
• A General Acid-Catalyzed Anion Breakdown Associated with an E1cB Reaction in the Hydrolysis of Aryl N-(Substituted Phenylsulfonyl)carbamates
  作者：Alain Vigroux、Michel Bergon、Catherine Bergonzi、Pierre Tisnes

  DOI：10.1021/ja00105a020

  日期：1994.12

  The hydrolysis of aryl N-(substituted phenylsulfonyl)carbamates at 50 degrees C in the pH range 0-13.5 leading to substituted benzenesulfonamides and phenols involves acyl group transfer. Reaction rates were measured spectrophotometrically and are independent of the concentration of the catalyst for buffers of pK(BH) > 8. With more acidic buffers, a general acid catalysis is observed for the hydrolysis of phenyl N-(phenylsulfonyl)carbamate la (pK, = 2.85) leading to a Bronsted relation (alpha = 0.46) including hydronium ion while it does not occur for 4-cyanophenyl N-(phenylsulfonyl)carbamate 1d. In alkaline media, the values of the entropies of activation are positive and lie between 0.20 and 15.0 cal mol(-1) K-1. The Hammett rho(-) value for the expulsion rate k(p) of phenolate ion from aryl N-(phenylsulfonyl)carbamates is positive (rho(-) = +2.93) while, for phenyl N-(substituted phenylsulfonyl)carbamates it is negative (rho = -0.66). An electrophilic intermediate, phenylsulfonyl isocyanate, was trapped with piperidine to give N-(piperidinocarbonyl)benzenesulfonamide. These results are consistent with an elimination-addition mechanism A(rh)D(H) + D-N (E1cB). In HCl solutions, solvent isotope effects k(obsd)(H2O)/k(obsd)(D2O) equal to 1.68 for 1a and 2.46 for Id have been measured. For molar concentrations of water lying between 40 and 55.5 M(-1), the rate of hydrolysis of la in 0.5 M HCl solutions increases in the presence of dioxan while it decreases with chloral. The Hammett rho values for the reactivity k,in acidic media of aryl N-(phenylsulfonyl)carbamates (rho = +0.87) and for phenyl N-(substituted phenylsulfonyl)carbamates (rho = +0.22) agree with the protonation of the oxygen atom of the leaving group. Trapping experiment for the hydrolysis of 1a and 1d in a chloroacetate buffer in the presence of 4-chloroaniline gave in both cases N-(((4-chlorophenyl)amino)carbonyl)sulfo. Reaction carried out in (H2O)-O-18 with O-16- containing substrate indicates that there is no exchange from water to the carbonyl group of the sulfonylcarbamate. These data support a general acid catalysis of the breakdown of the anion which cuts in depending on the leaving group ability.
• SCHAUMANN E.; DIETZ J.; KAUSCH E.; SCHMERSE G. C., CHEM. BER., 120,(1987) N 3, 339-344
  作者：SCHAUMANN E.、 DIETZ J.、 KAUSCH E.、 SCHMERSE G. C.

  DOI：——

  日期：——
• US7153925B2
  申请人：——

  公开号：US7153925B2

  公开（公告）日：2006-12-26
• Sulfonylureido thiazoles as fructose-1,6-bisphosphatase inhibitors for the treatment of Type-2 diabetes
  作者：Eric Kitas、Peter Mohr、Bernd Kuhn、Paul Hebeisen、Hans Peter Wessel、Wolfgang Haap、Armin Ruf、Jörg Benz、Catherine Joseph、Walter Huber、Ruben Alvarez Sanchez、Axel Paehler、Agnes Benardeau、Marcel Gubler、Brigitte Schott、Effie Tozzo

  DOI：10.1016/j.bmcl.2009.11.093

  日期：2010.1

  Sulfonylureido thiazoles were identified from a HTS campaign and optimized through a combination of structure-activity studies, X-ray crystallography and molecular modeling to yield potent inhibitors of fructose-1,6-bisphosphatase. Compound 12 showed favorable ADME properties, for example, F=70%, and a robust 32% glucose reduction in the acute db/db mouse model for Type-2 diabetes.