3-phenyl-2-[prop-2-ynyl(toluene-4-sulfonyl)amino]propionic acid prop-2-ynyl ester | 1378523-88-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-phenyl-2-[prop-2-ynyl(toluene-4-sulfonyl)amino]propionic acid prop-2-ynyl ester
• CAS: 1378523-88-6
• 化学式: C₂₂H₂₁NO₄S
• 分子量: 395.479
• InChiKey: WSECTRUFCORGPN-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-phenyl-2-[prop-2-ynyl(toluene-4-sulfonyl)amino]propionic acid prop-2-ynyl ester 在 锂硼氢 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 7.0h， 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：

  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：

  N-(对甲苯磺酰)-L-苯丙氨酸 、 3-溴丙炔 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 3-phenyl-2-[prop-2-ynyl(toluene-4-sulfonyl)amino]propionic acid prop-2-ynyl ester
  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