N,2-dimethylpropane-2-sulfonamide | 76699-23-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N,2-dimethylpropane-2-sulfonamide
• 英文别名: N,2-dimethyl-2-propanesulfonamide
• CAS: 76699-23-5
• 化学式: C₅H₁₃NO₂S
• 分子量: 151.23
• InChiKey: DTDZACLCPOMJSU-UHFFFAOYSA-N

物化性质

• 沸点：
  205.8±23.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxybutan-2-yl)-3-methylpiperidin-2-one 、 N,2-dimethylpropane-2-sulfonamide 在 氰基亚甲基三正丁基膦 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 N-((S)-2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)butyl)-N,2-dimethylpropane-2-sulfonamide
  参考文献：
  名称：

  Discovery of AMG 232, a Potent, Selective, and Orally Bioavailable MDM2–p53 Inhibitor in Clinical Development

  摘要：

  We recently reported the discovery of AM-8553 (1), a potent and selective piperidinone inhibitor of the MDM2-p53 interaction. Continued research investigation of the N-alkyl substituent of this series, focused in particular on a previously underutilized interaction in a shallow cleft on the MDM2 surface, led to the discovery of a one-carbon tethered sulfone which gave rise to substantial improvements in biochemical and cellular potency. Further investigation produced AMG 232 (2), which is currently being evaluated in human clinical trials for the treatment of cancer. Compound 2 is an extremely potent MDM2 inhibitor (SPR KD = 0.045 nM, SJSA-1 EdU IC50 = 9.1 nM), with remarkable pharmacokinetic properties and in vivo antitumor activity in the SJSA-1 osteosarcoma xenograft model (ED50 = 9.1 mg/kg).

  DOI：

  10.1021/jm401753e
• 作为产物：
  描述：

  N-methyl-tert-butylsulfinamide 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以50%的产率得到N,2-dimethylpropane-2-sulfonamide
  参考文献：
  名称：

  Proton and carbon-13 CIDNP study of the radical rearrangement involved in the reaction of tert-butylsulfinyl chloride with N-hydroxysulfonamides

  摘要：

  DOI：

  10.1021/jo00318a033

文献信息

• 一种在水中合成N-甲基磺酰胺的方法
  申请人：南京理工大学

  公开号：CN110857278B

  公开（公告）日：2022-04-15

  本发明公开了一种在水中合成N‑甲基磺酰胺的方法，以磺酰胺与甲醇为原料，采用过渡金属铱催化剂催化N‑甲基化反应。本发明使用无毒无害的水做溶剂，避免使用有机试剂；反应只生成水作为副产物，无环境危害；反应温度相对于之前的条更加温和；反应只生成单甲基化产物，具有良好的选择性；反应原子经济性高，具有广阔的应用前景。
• N-Methylation of Amines with Methanol in Aqueous Solution Catalyzed by a Water-Soluble Metal–Ligand Bifunctional Dinuclear Iridium Catalyst
  作者：Chong Meng、Peng Liu、Nguyen Thanh Tung、Xingyou Han、Feng Li

  DOI：10.1021/acs.joc.9b03411

  日期：2020.5.1

  The N-methylation of amines with methanol in aqueous solution was proposed and accomplished by using a water-soluble metal-ligand bifunctional dinuclear iridium catalyst. In the presence of [(Cp*IrCl)2(thbpym)][Cl]2 (1 mol %), a range of desirable products were obtained in high yields under environmentally benign conditions. Notably, this research exhibited the potential of transition metal-catalyzed

  提出了胺与甲醇在水溶液中的N-甲基化反应，并通过使用水溶性金属-配体双官能双核铱催化剂完成。在[（Cp * IrCl）2（thbpym）] [Cl] 2（1mol％）的存在下，在环境友好的条件下以高收率获得了一系列期望的产物。值得注意的是，这项研究显示了过渡金属催化的甲醇作为C1来源的潜在活化作用，用于在水溶液中构建CN键。
• Recyclable covalent triazine framework-supported iridium catalyst for the N-methylation of amines with methanol in the presence of carbonate
  作者：Peng Liu、Jiazhi Yang、Yao Ai、Shushu Hao、Xiaozhong Chen、Feng Li

  DOI：10.1016/j.jcat.2021.02.030

  日期：2021.4

  An iridium complex Cp*Ir@CTF, which is synthesized by the coordinative immobilization of [Cp*IrCl2]2 on a functionalized covalent triazine framework (CTF), was found to be a general and highly efficient catalyst for the N-methylation of amines with methanol in the presence of carbonate. Under environmentally benign conditions, a variety of desirable products were obtained in high yields with complete

  铱络合物Cp * Ir @ CTF是通过将[Cp * IrCl 2 ] 2配位固定在功能化的共价三嗪骨架（CTF）上合成的，它是一种通用的高效N-甲基化催化剂在碳酸盐的存在下，将胺与甲醇反应。在环境友好的条件下，以高收率获得了各种理想的产品，具有完全的选择性和对官能团的友好性。此外，合成的催化剂可以通过简单的过滤进行再循环，而在第六次循环后没有明显的催化活性损失。值得注意的是，这项研究显示了共价三嗪骨架负载的过渡金属催化剂在氢自动转移过程中的潜力。
• <i>N</i>-Methylation of Amines with Methanol in the Presence of Carbonate Salt Catalyzed by a Metal–Ligand Bifunctional Ruthenium Catalyst [(<i>p</i>-cymene)Ru(2,2′-bpyO)(H₂O)]
  作者：Peng Liu、Nguyen Thanh Tung、Xiangchao Xu、Jiazhi Yang、Feng Li

  DOI：10.1021/acs.joc.0c02685

  日期：2021.2.5
• Discovery of AMG 232, a Potent, Selective, and Orally Bioavailable MDM2–p53 Inhibitor in Clinical Development
  作者：Daqing Sun、Zhihong Li、Yosup Rew、Michael Gribble、Michael D. Bartberger、Hilary P. Beck、Jude Canon、Ada Chen、Xiaoqi Chen、David Chow、Jeffrey Deignan、Jason Duquette、John Eksterowicz、Benjamin Fisher、Brian M. Fox、Jiasheng Fu、Ana Z. Gonzalez、Felix Gonzalez-Lopez De Turiso、Jonathan B. Houze、Xin Huang、Min Jiang、Lixia Jin、Frank Kayser、Jiwen (Jim) Liu、Mei-Chu Lo、Alexander M. Long、Brian Lucas、Lawrence R. McGee、Joel McIntosh、Jeff Mihalic、Jonathan D. Oliner、Tao Osgood、Matthew L. Peterson、Philip Roveto、Anne Y. Saiki、Paul Shaffer、Maria Toteva、Yingcai Wang、Yu Chung Wang、Sarah Wortman、Peter Yakowec、Xuelei Yan、Qiuping Ye、Dongyin Yu、Ming Yu、Xiaoning Zhao、Jing Zhou、Jiang Zhu、Steven H. Olson、Julio C. Medina

  DOI：10.1021/jm401753e

  日期：2014.2.27

  We recently reported the discovery of AM-8553 (1), a potent and selective piperidinone inhibitor of the MDM2-p53 interaction. Continued research investigation of the N-alkyl substituent of this series, focused in particular on a previously underutilized interaction in a shallow cleft on the MDM2 surface, led to the discovery of a one-carbon tethered sulfone which gave rise to substantial improvements in biochemical and cellular potency. Further investigation produced AMG 232 (2), which is currently being evaluated in human clinical trials for the treatment of cancer. Compound 2 is an extremely potent MDM2 inhibitor (SPR KD = 0.045 nM, SJSA-1 EdU IC50 = 9.1 nM), with remarkable pharmacokinetic properties and in vivo antitumor activity in the SJSA-1 osteosarcoma xenograft model (ED50 = 9.1 mg/kg).