propynoic acid (2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl)amide | 1194509-18-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: propynoic acid (2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl)amide
• 英文别名: N-(2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl)prop-2-ynamide
• CAS: 1194509-18-6
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: WPZAIXPZTFYCAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  propynoic acid (2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl)amide 在 aluminum (III) chloride 、 sodium iodide 、 水 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 18.0h， 以89%的产率得到(Z)-N-(2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl)-3-iodoacrylamide
  参考文献：
  名称：

  AlCl3–NaI(NaBr)–t-BuOH: mild, chemo- and stereoselective reagents for hydrohalogenation of propiolic derivatives

  摘要：

  (Z)-beta-lodo-propenamides and -beta-iodo-propenoic esters were selectively prepared in high yields, at room temperature, through reaction of 2-propynamides and 2-propynoic esters, respectively, with AlCl3 and Nal in the presence of t-BuOH in dichloromethane. These experimental conditions are compatible with the presence of acid sensitive acetal groups. Alternative use of EtOH or H2O in place of t-BuOH was investigated. (Z)-Bromo-propenamides and corresponding esters were prepared according to a similar procedure using sodium bromide in refluxing acetonitrile. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2009.08.032
• 作为产物：
  描述：

  2,2-dimethyl-4-phenyl-1,3-dioxan-5-amine 、 丙炔酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到propynoic acid (2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl)amide
  参考文献：
  名称：

  AlCl3–NaI(NaBr)–t-BuOH: mild, chemo- and stereoselective reagents for hydrohalogenation of propiolic derivatives

  摘要：

  (Z)-beta-lodo-propenamides and -beta-iodo-propenoic esters were selectively prepared in high yields, at room temperature, through reaction of 2-propynamides and 2-propynoic esters, respectively, with AlCl3 and Nal in the presence of t-BuOH in dichloromethane. These experimental conditions are compatible with the presence of acid sensitive acetal groups. Alternative use of EtOH or H2O in place of t-BuOH was investigated. (Z)-Bromo-propenamides and corresponding esters were prepared according to a similar procedure using sodium bromide in refluxing acetonitrile. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2009.08.032

文献信息

• AlCl3–NaI(NaBr)–t-BuOH: mild, chemo- and stereoselective reagents for hydrohalogenation of propiolic derivatives
  作者：Laurence Feray、Patricia Perfetti、Michèle Bertrand

  DOI：10.1016/j.tet.2009.08.032

  日期：2009.10

  (Z)-beta-lodo-propenamides and -beta-iodo-propenoic esters were selectively prepared in high yields, at room temperature, through reaction of 2-propynamides and 2-propynoic esters, respectively, with AlCl3 and Nal in the presence of t-BuOH in dichloromethane. These experimental conditions are compatible with the presence of acid sensitive acetal groups. Alternative use of EtOH or H2O in place of t-BuOH was investigated. (Z)-Bromo-propenamides and corresponding esters were prepared according to a similar procedure using sodium bromide in refluxing acetonitrile. (C) 2009 Published by Elsevier Ltd.