2-tolylsulfonyl N-methylacetamide | 500586-84-5

• 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: 2-tolylsulfonyl N-methylacetamide
• 英文别名: N-methyl-2-(4-methylphenyl)sulfonylacetamide
• CAS: 500586-84-5
• 化学式: C₁₀H₁₃NO₃S
• 分子量: 227.284
• InChiKey: DCBRSPFZIOSVKW-UHFFFAOYSA-N

物化性质

• 沸点：
  484.7±45.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-tolylsulfonyl N-methylacetamide 在 Raney nickel 2800 三氟化硼乙醚 、 氢气 、 sodium hydride 、 magnesium sulfate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， -30.0~20.0 ℃ 、275.8 kPa 条件下， 反应 56.75h， 生成 1-methyl-8,9-(methylenedioxy)-3-(toluene-4-sulfonyl)-1H-benzo[h]quinolin-2-one
  参考文献：
  名称：

  A facile approach to polysubstituted 2-pyridones. Application to the synthesis of 3,4-disubstituted isoquinolinone and total synthesis of oxyisoterihanine

  摘要：

  A facile approach to polysubstituted 2-pyridones from 1-benzyl- 5,6-dialkyl-3-(4-toluenesulfonyl) pyridin-2-one was described. A new approach to 3,4-disubstituted isoquinolinone and total synthesis of oxyisoterihanine will also be reported. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.101
• 作为产物：
  描述：

  2-氯-N-甲基乙酰胺 、 sodium 4-methylbenzenesulfinate 以 1,4-二氧六环 、 水 为溶剂， 反应 10.0h， 生成 2-tolylsulfonyl N-methylacetamide
  参考文献：
  名称：

  Chang, Meng-Yang; Chen, Shui-Tein; Chang, Nein-Chen, Heterocycles, 2002, vol. 57, # 12, p. 2321 - 2334

  摘要：

  DOI：

文献信息

• One-pot facile conversion of Baylis–Hillman adduct into N-alkyl 3-(E)-alkylidene-5-substituted sulfonylpiperidine-2,6-dione. Formal synthesis of tacamonine
  作者：Chung-Yi Chen、Meng-Yang Chang、Ru-Ting Hsu、Shui-Tein Chen、Nein-Chen Chang

  DOI：10.1016/j.tetlet.2003.08.053

  日期：2003.11

  stepwise [3+3] strategy to N-alkyl 3-(E)-alkylidene-5-substituted sulfonylpiperidine-2,6-dione 1 used various N-alkyl α-substituted sulfonylacetamides 2 and α,β-unsaturated esters 3 as starting materials. α,β-Unsaturated esters 3 were generated by Baylis–Hillman reaction. A ring closure mechanism was proposed for the reactions. This method provides a convenient formal synthesis of tacamonine.

  N-烷基3-（E）-亚烷基-5-取代的磺酰基哌啶-2,6-二酮1的逐步[3 + 3]策略使用各种N-烷基α-取代的磺酰基乙酰胺2和α，β-不饱和酯3作为起始材料。α，β-不饱和酯3是通过Baylis-Hillman反应生成的。提出了反应的闭环机理。该方法提供了塔卡莫宁的方便的形式合成。
• Stereoselective Synthesis of Constrained Azacyclic Hydroxyethylene Isosteres as Aspartic Protease Inhibitors: Dipolar Cycloaddition and Related Methodologies toward Branched Pyrrolidine and Pyrrolidinone Carboxylic Acids
  作者：Stephen Hanessian、Hongying Yun、Yihua Hou、Marina Tintelnot-Blomley

  DOI：10.1021/jo050740w

  日期：2005.8.1

  [GRAPHICS]The synthesis of three vicinally substituted azacyclic carboxylic acids in enantiopure form was achieved from a common (x-amino aldehyde originating from (L)-leucine. Pyrrolidines and pyrrolidinones were elaborated from a,beta-unsaturated gamma-hydroxy-delta-amino acids via azomethine ylide 1,3dipolar addition and conjugate addition/cyclization strategies, respectively. The azacyclic amino acids were incorporated in a pseudopeptide now encompassing a hydroxyethylene isostere. Low nanomolar inhibition of BACE1, an enzyme implicated in the cascade of events leading to plaque formation in Alzheimer's disease, was found with a pyrrolidinone analogue.
• US9822281B2
  申请人：——

  公开号：US9822281B2

  公开（公告）日：2017-11-21
• Chang, Meng-Yang; Chen, Shui-Tein; Chang, Nein-Chen, Heterocycles, 2002, vol. 57, # 12, p. 2321 - 2334
  作者：Chang, Meng-Yang、Chen, Shui-Tein、Chang, Nein-Chen

  DOI：——

  日期：——
• A facile approach to polysubstituted 2-pyridones. Application to the synthesis of 3,4-disubstituted isoquinolinone and total synthesis of oxyisoterihanine
  作者：Tsung-Hsiu Tsai、Wen-Hsuan Chung、Jung-Kai Chang、Ru-Ting Hsu、Nein-Chen Chang

  DOI：10.1016/j.tet.2007.06.101

  日期：2007.9

  A facile approach to polysubstituted 2-pyridones from 1-benzyl- 5,6-dialkyl-3-(4-toluenesulfonyl) pyridin-2-one was described. A new approach to 3,4-disubstituted isoquinolinone and total synthesis of oxyisoterihanine will also be reported. (C) 2007 Elsevier Ltd. All rights reserved.