2-Allyl-thiobenzoic acid S-[2-(2-tert-butoxycarbonylamino-phenyl)-ethyl] ester | 193806-59-6

• 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-Allyl-thiobenzoic acid S-[2-(2-tert-butoxycarbonylamino-phenyl)-ethyl] ester
• 英文别名: S-[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]ethyl] 2-prop-2-enylbenzenecarbothioate
• CAS: 193806-59-6
• 化学式: C₂₃H₂₇NO₃S
• 分子量: 397.538
• InChiKey: PJULMMYZJYKBGJ-UHFFFAOYSA-N

物化性质

• 沸点：
  497.8±45.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Allyl-thiobenzoic acid S-[2-(2-tert-butoxycarbonylamino-phenyl)-ethyl] ester 在 盐酸 、 tetrafluoroboric acid 、 sodium iodide 、 亚硝酸异戊酯 作用下， 以 乙醇 、 乙酸乙酯 、 丙酮 为溶剂， 反应 6.5h， 生成 3-iodomethyl-isochroman-1-one
  参考文献：
  名称：

  Generation and Cyclization of Acyl Radicals from Thiol Esters Under Nonreducing, Tin-Free Conditions

  摘要：

  The preparation of 2-(2-((tert-butyloxycarbonyl)amino)phenyl)ethyl mercaptan from 2-(2-amino-phenyl)ethanol is described. This thiol is condensed with a series of suitably unsaturated carboxylic acids to give a series of thiol esters. The Boc group is removed and the amine reacted with isoamyl nitrite to give a series of diazonium salts. Exposure to iodide in acetone solution then generates the aryl radical, which undergoes intramolecular homolytic substitution at sulfur with liberation of the acylradical. Following acyl radical cyclization, quenching by iodine and then elimination of HI leads to the isolation of alpha-methylene cycloalkanones in good yield.

  DOI：

  10.1021/jo970500j
• 作为产物：
  描述：

  2-氨基苯乙醇 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.83h， 生成 2-Allyl-thiobenzoic acid S-[2-(2-tert-butoxycarbonylamino-phenyl)-ethyl] ester
  参考文献：
  名称：

  Generation and Cyclization of Acyl Radicals from Thiol Esters Under Nonreducing, Tin-Free Conditions

  摘要：

  The preparation of 2-(2-((tert-butyloxycarbonyl)amino)phenyl)ethyl mercaptan from 2-(2-amino-phenyl)ethanol is described. This thiol is condensed with a series of suitably unsaturated carboxylic acids to give a series of thiol esters. The Boc group is removed and the amine reacted with isoamyl nitrite to give a series of diazonium salts. Exposure to iodide in acetone solution then generates the aryl radical, which undergoes intramolecular homolytic substitution at sulfur with liberation of the acylradical. Following acyl radical cyclization, quenching by iodine and then elimination of HI leads to the isolation of alpha-methylene cycloalkanones in good yield.

  DOI：

  10.1021/jo970500j