(S)-4-methyl-N-(1-oxo-3-phenylpropan-2-yl)-N-(prop-2-yn-1-yl)benzenesulfonamide | 1232168-24-9

• 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: (S)-4-methyl-N-(1-oxo-3-phenylpropan-2-yl)-N-(prop-2-yn-1-yl)benzenesulfonamide
• 英文别名: 4-methyl-N-[(2S)-1-oxo-3-phenylpropan-2-yl]-N-prop-2-ynylbenzenesulfonamide
• CAS: 1232168-24-9
• 化学式: C₁₉H₁₉NO₃S
• 分子量: 341.431
• InChiKey: QQGPBMKMCHKXKZ-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-methyl-N-(1-oxo-3-phenylpropan-2-yl)-N-(prop-2-yn-1-yl)benzenesulfonamide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.59h， 生成 3-benzyl-2-(4-methoxyphenyl)-6-methyl-4-(toluene-4-sulfonyl)-3,4-dihydro-2H-[1,4]oxazine
  参考文献：
  名称：

  A New Approach to 1,4-Oxazines and 1,4-Oxazepines via Base-Promoted Exo Mode Cyclization of Alkynyl Alcohols: Mechanism and DFT Studies

  摘要：

  A new approach was developed to synthesize 1,4-oxazine and 1,4-oxazepine derivatives without solvent and metal. Regioselective cyclization occurred to afford exclusively the exo-clig product, and stereochemistry was studied by circular dichroism and specific optical rotation techniques. The Grignard reaction is a key synthetic step to produce high diastereomeric compounds via Cram's rule and was well supported by DFT calculations. A hydroalkoxylation mechanism was proposed and supported by DFT calculations.

  DOI：

  10.1021/ol301219c
• 作为产物：
  描述：

  methyl (2S)-2-{N-(prop-2-ynyl)-4-toluenesulfonamido}-3-phenylpropanoate 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (S)-4-methyl-N-(1-oxo-3-phenylpropan-2-yl)-N-(prop-2-yn-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Diastereoselective Syntheses of Functionalized Five-Membered Carbocycles and Heterocycles by a SmI₂-Promoted Intramolecular Coupling of Bromoalkynes and α,β-Unsaturated Esters

  摘要：

  An intramolecular coupling of bromoalkynes with alpha,beta-unsaturated esters afforded functionalized five-membered carbocycles and heterocycles with high diastereoselectivities in excellent yields. The vinyl bromides newly generated as the products serve as adequate intermediates for further chemical modification.

  DOI：

  10.1021/ol101034s

文献信息

• Straightforward synthesis of pyrrolo[3,4-b]quinolines through intramolecular Povarov reactions
  作者：Abdulrahman I. Almansour、Natarajan Arumugam、Raju Suresh Kumar、J. Carlos Menéndez、Hazem A. Ghabbour、Hoong-Kun Fun、Raju Ranjith Kumar

  DOI：10.1016/j.tetlet.2015.10.107

  日期：2015.12

  A series of novel pyrrolo[3,4-b]quinolines have been synthesized from N-alkynyl aldehydes and various substituted arylamines in good to excellent yields utilizing an intramolecular Povarov reaction catalyzed by boron trifluoride diethyl etherate as the key final step.

  利用三氟化硼二乙基醚化物催化的分子内Povarov反应，由N-炔基醛和各种取代的芳基胺以良好至极好的收率合成了一系列新型的吡咯并[3,4- b ]喹啉。