4-<(Naphthalen-2-ylthio)carbonyl>butylcarboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-<(Naphthalen-2-ylthio)carbonyl>butylcarboxylic acid ethyl ester
• 英文别名: Ethyl 5-naphthalen-2-ylsulfanyl-5-oxopentanoate
• 化学式: C₁₇H₁₈O₃S
• 分子量: 302.394
• InChiKey: JXAWXWJSWCKTNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-<(Naphthalen-2-ylthio)carbonyl>butylcarboxylic acid ethyl ester 在 1,4-环己二烯 作用下， 以 苯 为溶剂， 反应 110.0h， 以99%的产率得到5-氧代戊酸乙酯
  参考文献：
  名称：

  Generation of Acyl Radicals From 2-Naphthyl Thioesters

  摘要：

  A series of S-2-naphthyl thioesters were synthesized from the corresponding carboxylic acids or acid chlorides. Irradiation of these thioesters in the presence of a hydrogen source (i.e., 1,4-cyclohexadiene) generated the corresponding aldehydes. In this fashion, primary, secondary, tertiary, and aryl carboxylic acids were converted to the aldehydes in high yields. Intramolecular radical cyclization reactions support the hypothesis that the reaction proceeds via the formation of acyl radicals. The formation of aldehydes was not perturbed by possible Norrish Type II reactions.

  DOI：

  10.1021/jo00088a053
• 作为产物：
  描述：

  戊二酸单乙酯酰氯 、 2-萘硫醇 在 吡啶 作用下， 以 苯 为溶剂， 反应 0.5h， 以98%的产率得到4-<(Naphthalen-2-ylthio)carbonyl>butylcarboxylic acid ethyl ester
  参考文献：
  名称：

  Generation of Acyl Radicals From 2-Naphthyl Thioesters

  摘要：

  A series of S-2-naphthyl thioesters were synthesized from the corresponding carboxylic acids or acid chlorides. Irradiation of these thioesters in the presence of a hydrogen source (i.e., 1,4-cyclohexadiene) generated the corresponding aldehydes. In this fashion, primary, secondary, tertiary, and aryl carboxylic acids were converted to the aldehydes in high yields. Intramolecular radical cyclization reactions support the hypothesis that the reaction proceeds via the formation of acyl radicals. The formation of aldehydes was not perturbed by possible Norrish Type II reactions.

  DOI：

  10.1021/jo00088a053

文献信息

• Penn John H., Liu Fang, J. Org. Chem, 59 (1994) N 9, S 2608-2612
  作者：Penn John H., Liu Fang

  DOI：——

  日期：——
• Generation of Acyl Radicals From 2-Naphthyl Thioesters
  作者：John H. Penn、Fang Liu

  DOI：10.1021/jo00088a053

  日期：1994.5

  A series of S-2-naphthyl thioesters were synthesized from the corresponding carboxylic acids or acid chlorides. Irradiation of these thioesters in the presence of a hydrogen source (i.e., 1,4-cyclohexadiene) generated the corresponding aldehydes. In this fashion, primary, secondary, tertiary, and aryl carboxylic acids were converted to the aldehydes in high yields. Intramolecular radical cyclization reactions support the hypothesis that the reaction proceeds via the formation of acyl radicals. The formation of aldehydes was not perturbed by possible Norrish Type II reactions.