2-(acetamidomethyl)-3-methylfuran | 239123-81-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(acetamidomethyl)-3-methylfuran
• 英文别名: N-((3-methylfuran-2-yl)methyl)acetamide；N-[(3-methylfuran-2-yl)methyl]acetamide
• CAS: 239123-81-0
• 化学式: C₈H₁₁NO₂
• 分子量: 153.181
• InChiKey: QLQMFXVKBIVMOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(acetamidomethyl)-3-methylfuran 在 三氯化铝 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 4-<2-(acetamidomethyl)-3-methylfuran-5-yl>-2-<<2-(2-methoxyphenyl)ethyl>guanidino>thiazole hydrochloride
  参考文献：
  名称：

  Anti-Helicobacter pylori Agents. 3. 2-[(Arylalkyl)guanidino]-4-furylthiazoles

  摘要：

  A series of 2-[(arylalkyl)guanidinol-4-[(5-acetamidomethyl)furan-2-yl]thiazoles and some 4-acetamidomethyl positional isomers were synthesized and evaluated for antimicrobial activity against Helicobacter pylori. Among the compounds that had potent antimicrobial activity (MIC < 0.1 mu g/mL), compounds 31 and 36 additionally possessed H2 antagonist and gastric antisecretory activities. Though compound 51, an analogue incorporating a methyl group onto the furan nucleus of 36, and compound 54, a positional isomer of 51, also showed potent anti-H. pylori activity, the H2 antagonism profile was eliminated from these compounds. Thus, two types of potent anti-H. pylori agents could be derived from the same scaffold.

  DOI：

  10.1021/jm9900671
• 作为产物：
  描述：

  3-甲基-2-呋喃甲酸甲酯 在 sodium methylate 、 formamide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-(acetamidomethyl)-3-methylfuran
  参考文献：
  名称：

  取代对硫醇诱导的氧杂降冰片二烯断裂的影响

  摘要：

  氧杂降冰片二烯 (OND) 与硫醇进行简单的迈克尔加成，然后通过逆狄尔斯-阿尔德 (rDA) 反应进行片段化，这是亲电可切割键之间的独特两步序列。研究了 rDA 反应速率与呋喃结构的函数关系，发现 2 位和 5 位的取代基影响最大，碎裂率与吸电子能力呈负相关。密度泛函理论计算提供了与实验测量的 OND rDA 率的极好相关性。

  DOI：

  10.1021/acs.orglett.1c01164

文献信息

• The Influence of Substitution on Thiol-Induced Oxanorbornadiene Fragmentation
  作者：Lucrezia De Pascalis、Mei-Kwan Yau、Dennis Svatunek、Zhuoting Tan、Srinivas Tekkam、K. N. Houk、M. G. Finn

  DOI：10.1021/acs.orglett.1c01164

  日期：2021.5.7

  Oxanorbornadienes (ONDs) undergo facile Michael addition with thiols and then fragment by a retro-Diels–Alder (rDA) reaction, a unique two-step sequence among electrophilic cleavable linkages. The rDA reaction rate was explored as a function of the furan structure, with substituents at the 2- and 5-positions found to be the most influential and the fragmentation rate to be inversely correlated with

  氧杂降冰片二烯 (OND) 与硫醇进行简单的迈克尔加成，然后通过逆狄尔斯-阿尔德 (rDA) 反应进行片段化，这是亲电可切割键之间的独特两步序列。研究了 rDA 反应速率与呋喃结构的函数关系，发现 2 位和 5 位的取代基影响最大，碎裂率与吸电子能力呈负相关。密度泛函理论计算提供了与实验测量的 OND rDA 率的极好相关性。
• Anti-<i>Helicobacter pylori</i> Agents. 3. 2-[(Arylalkyl)guanidino]-4-furylthiazoles
  作者：Yousuke Katsura、Shigetaka Nishino、Mitsuko Ohno、Kazuo Sakane、Yoshimi Matsumoto、Chizu Morinaga、Hirohumi Ishikawa、Hisashi Takasugi

  DOI：10.1021/jm9900671

  日期：1999.7.1

  A series of 2-[(arylalkyl)guanidinol-4-[(5-acetamidomethyl)furan-2-yl]thiazoles and some 4-acetamidomethyl positional isomers were synthesized and evaluated for antimicrobial activity against Helicobacter pylori. Among the compounds that had potent antimicrobial activity (MIC < 0.1 mu g/mL), compounds 31 and 36 additionally possessed H2 antagonist and gastric antisecretory activities. Though compound 51, an analogue incorporating a methyl group onto the furan nucleus of 36, and compound 54, a positional isomer of 51, also showed potent anti-H. pylori activity, the H2 antagonism profile was eliminated from these compounds. Thus, two types of potent anti-H. pylori agents could be derived from the same scaffold.