4-methyl-N-[(2S)-4-methyl-1-oxopentan-2-yl]-N-prop-2-ynylbenzenesulfonamide | 1232168-40-9

• 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: 4-methyl-N-[(2S)-4-methyl-1-oxopentan-2-yl]-N-prop-2-ynylbenzenesulfonamide
• CAS: 1232168-40-9
• 化学式: C₁₆H₂₁NO₃S
• 分子量: 307.414
• InChiKey: BBWIWCLYZRRWDR-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  4-methyl-N-[(2S)-4-methyl-1-oxopentan-2-yl]-N-prop-2-ynylbenzenesulfonamide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.59h， 生成 3-isobutyl-2-(2-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：

  (S)-4-methyl-2-(toluene-4-sulfonamido)pentanoic acid 在 锂硼氢 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 11.0h， 生成 4-methyl-N-[(2S)-4-methyl-1-oxopentan-2-yl]-N-prop-2-ynylbenzenesulfonamide
  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

文献信息

• Diastereoselective Syntheses of Functionalized Five-Membered Carbocycles and Heterocycles by a SmI₂-Promoted Intramolecular Coupling of Bromoalkynes and α,β-Unsaturated Esters
  作者：Kazunori Takahashi、Toshio Honda

  DOI：10.1021/ol101034s

  日期：2010.7.2

  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.