propynoic acid (2,2-diethoxyethyl)amide | 1194509-17-5

• 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: propynoic acid (2,2-diethoxyethyl)amide
• 英文别名: N-(2,2-diethoxyethyl)prop-2-ynamide
• CAS: 1194509-17-5
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: PQQLDYVRVQGLKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.13
• 重原子数：
  13.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  propynoic acid (2,2-diethoxyethyl)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87%的产率得到(Z)-N-(2,2-diethoxyethyl)-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：

  氨基乙醛缩二乙醇 、 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71%的产率得到propynoic acid (2,2-diethoxyethyl)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

• Investigation of the lipase-catalysed reaction of aliphatic amines with ethyl propiolate as a route to N-substituted propiolamides
  作者：Simon Bonte、Ioana Otilia Ghinea、Isabelle Baussanne、Jean-Paul Xuereb、Rodica Dinica、Martine Demeunynck

  DOI：10.1016/j.tet.2013.04.093

  日期：2013.7

  The lipase-catalysed reaction of aliphatic amine with ethyl propiolate was investigated using benzylamine as reference amine. The conditions were optimised to favour the 1,2-addition, i.e., formation of N-benzylprop-2-ynamide, versus the 1,4-addition. Immobilised Candida antarctica lipase (CALB) was found to be the most efficient enzyme, and the reactions were performed in solvents, such as tBME, dioxane

  以苄胺为参比胺，研究了脂肪胺与丙酸乙酯的脂肪酶催化反应。优化条件以有利于1，2-加成，即形成N-苄基丙-2-炔酰胺，而不是1，4-加成。发现固定化的南极假丝酵母脂肪酶（CALB）是最有效的酶，并且反应在溶剂中进行，例如t BME，二恶烷或甲苯。该方法用于从脂肪族胺以良好至优异的产率制备丙丙酰胺。在相同条件下比较了O-和S-亲核试剂的反应性。