N,N-dimethyl sulfenamide

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-dimethyl sulfenamide
• 英文别名: N,N-dimethylaminothiol；N,N-dimethylthiohydroxylamine
• 化学式: C₂H₇NS
• 分子量: 77.1503
• InChiKey: JKTHTZCPLANQBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  4
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  4.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5R,6R)-6-(3-chlorophenyl)-5-(4-chlorophenyl)-4-((S)-1-hydroxybutan-2-yl)morpholin-3-one 、 N,N-dimethyl sulfenamide 在 cyanomethyl tributylphosphorane 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  MDM2-p53蛋白-蛋白质相互作用的选择性和强效吗啉酮抑制剂

  摘要：

  我们先前曾报道过发现AMG 232的发现，AMG 232是一种高效且选择性的MDM2-p53相互作用的哌啶酮抑制剂。我们不断寻找有效和多样的类似物，从而导致了新型吗啉酮MDM2抑制剂的发现。与哌啶酮系列相比，吗啉酮核心的这种变化对效能和代谢稳定性均具有显着影响。在此吗啉酮系列中，AM-8735以抑制剂的形式出现，具有显着的生化效能（HTRF IC 50 = 0.4 nM）和细胞效能（SJSA-1 EdU IC 50 = 25 nM）以及药代动力学特性。化合物4在ED 50的SJSA-1骨肉瘤异种移植模型中也显示出优异的抗肿瘤活性41 mg / kg。本文将描述对发现这种抑制剂以及吗啉酮与哌啶酮系列之间的关键区别的领先优化。

  DOI：

  10.1021/jm401767k
• 作为产物：
  描述：

  N,N-二甲基-2,2-二甲基乙烷次磺酰胺 369.1 ℃ 、1.07 kPa 条件下， 生成 异丁烷 、 N,N-dimethyl sulfenamide 、 异丁烯
  参考文献：
  名称：

  Gas-phase thermolysis oft-butylsulfenamides:N, N-dimethylt-butylsulfenamide, 2,6-dimethylpiperidinylt-butylsulfenamide, andN-t-butylt-butylsulfenamide

  摘要：

  The amide derivatives of t-butylsulfenic acid mentioned in the title have been thermolyzed in a stirred-flow reactor at temperatures of 273-390 degrees C and pressures of 7- 15 torr, using toluene as carrier gas, at residence times of 0.4-2 s. Isobutene formed in 95-99% yields, through order one reactions, following the Arrhenius equations: N,N-dimethyl t-butylsulfenamide:k(s(-1)) = 10(14.45+/-0.46) exp(-175 +/- 5 kj/molRT)2,6-dimethylpiperidyl t-butylsulfenamide:k(s(-1)) = 10(14.38+/-0.26) exp(-161 +/- 3 kj/molRT)N-t-butyl t-butylsulfenamide:k(s(-1)) = 10(14.75+/-0.37) exp(-184 +/- 7 kj/molRT)These thermolyses are considered to take place through unimolecular, four-center cyclic transition-state reaction mechanisms, giving rise to isobutene plus the corresponding S-unsubstituted thiohydroxylamines. The latter decompose outside the reactor at temperatures above -78 degrees C forming free sulfur and dimethylamine. 2,6-dimethylpiperidine, and t-butylamine, respectively. (C) 1996 John Wiley & Sons, Inc.

  DOI：

  10.1002/(sici)1097-4601(1996)28:5<353::aid-kin4>3.0.co;2-u

文献信息

• Gas-phase thermolysis oft-butylsulfenamides:N, N-dimethylt-butylsulfenamide, 2,6-dimethylpiperidinylt-butylsulfenamide, andN-t-butylt-butylsulfenamide
  作者：Gonzalo Martin、Julian Ascanio、Jesus Rodriguez

  DOI：10.1002/(sici)1097-4601(1996)28:5<353::aid-kin4>3.0.co;2-u

  日期：——

  The amide derivatives of t-butylsulfenic acid mentioned in the title have been thermolyzed in a stirred-flow reactor at temperatures of 273-390 degrees C and pressures of 7- 15 torr, using toluene as carrier gas, at residence times of 0.4-2 s. Isobutene formed in 95-99% yields, through order one reactions, following the Arrhenius equations: N,N-dimethyl t-butylsulfenamide:k(s(-1)) = 10(14.45+/-0.46) exp(-175 +/- 5 kj/molRT)2,6-dimethylpiperidyl t-butylsulfenamide:k(s(-1)) = 10(14.38+/-0.26) exp(-161 +/- 3 kj/molRT)N-t-butyl t-butylsulfenamide:k(s(-1)) = 10(14.75+/-0.37) exp(-184 +/- 7 kj/molRT)These thermolyses are considered to take place through unimolecular, four-center cyclic transition-state reaction mechanisms, giving rise to isobutene plus the corresponding S-unsubstituted thiohydroxylamines. The latter decompose outside the reactor at temperatures above -78 degrees C forming free sulfur and dimethylamine. 2,6-dimethylpiperidine, and t-butylamine, respectively. (C) 1996 John Wiley & Sons, Inc.
• Selective and Potent Morpholinone Inhibitors of the MDM2–p53 Protein–Protein Interaction
  作者：Ana Z. Gonzalez、John Eksterowicz、Michael D. Bartberger、Hilary P. Beck、Jude Canon、Ada Chen、David Chow、Jason Duquette、Brian M. Fox、Jiasheng Fu、Xin Huang、Jonathan B. Houze、Lixia Jin、Yihong Li、Zhihong Li、Yun Ling、Mei-Chu Lo、Alexander M. Long、Lawrence R. McGee、Joel McIntosh、Dustin L. McMinn、Jonathan D. Oliner、Tao Osgood、Yosup Rew、Anne Y. Saiki、Paul Shaffer、Sarah Wortman、Peter Yakowec、Xuelei Yan、Qiuping Ye、Dongyin Yu、Xiaoning Zhao、Jing Zhou、Steven H. Olson、Julio C. Medina、Daqing Sun

  DOI：10.1021/jm401767k

  日期：2014.3.27

  highly potent and selective piperidinone inhibitor of the MDM2–p53 interaction. Our continued search for potent and diverse analogues led to the discovery of novel morpholinone MDM2 inhibitors. This change to a morpholinone core has a significant impact on both potency and metabolic stability compared to the piperidinone series. Within this morpholinone series, AM-8735 emerged as an inhibitor with remarkable

  我们先前曾报道过发现AMG 232的发现，AMG 232是一种高效且选择性的MDM2-p53相互作用的哌啶酮抑制剂。我们不断寻找有效和多样的类似物，从而导致了新型吗啉酮MDM2抑制剂的发现。与哌啶酮系列相比，吗啉酮核心的这种变化对效能和代谢稳定性均具有显着影响。在此吗啉酮系列中，AM-8735以抑制剂的形式出现，具有显着的生化效能（HTRF IC 50 = 0.4 nM）和细胞效能（SJSA-1 EdU IC 50 = 25 nM）以及药代动力学特性。化合物4在ED 50的SJSA-1骨肉瘤异种移植模型中也显示出优异的抗肿瘤活性41 mg / kg。本文将描述对发现这种抑制剂以及吗啉酮与哌啶酮系列之间的关键区别的领先优化。