4-(chloromethyl)-2-methylfuran | 1207828-16-7

• 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: 4-(chloromethyl)-2-methylfuran
• 英文别名: 5-methyl-3-(chloromethyl)furan
• CAS: 1207828-16-7
• 化学式: C₆H₇ClO
• 分子量: 130.574
• InChiKey: ZYJHHJYGVMETDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(chloromethyl)-2-methylfuran 在 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 24.0h， 生成 3-ethyl-8-methyl-3H-furo[2,3-b]pyrazolo[4,3-f]quinoline-10-carbonitrile
  参考文献：
  名称：

  3H-呋喃[2,3-b]咪唑并[4,5-f]喹啉和3H-呋喃[2,3-b]吡唑并[4,3-f]喹啉作为新型抗菌剂的合成

  摘要：

  随着当前的挑战，由于抗生素耐药性细菌的增长，寻找新的抗生素化合物的需求也在增加。本研究获得了一些新的3 H-呋喃[2,3- b ]咪唑并[4,5- f ]喹啉和3 H-呋喃-[2,3- b ]吡唑并[4,3- f ]喹啉1-烷基-5-硝基-1 H-苯并咪唑和1-烷基-5-硝基-1 H-吲唑与2-(5-甲基呋喃-2-基)乙腈以高产率反应。新化合物的结构通过光谱(FT-IR, 1 H NMR, 13C NMR）和分析数据。抗菌筛选表明，标题化合物对革兰氏阳性菌和革兰氏阴性菌均非常有效，其 MIC 值与氨苄青霉素、青霉素 G 和磺胺甲恶唑等知名抗菌剂相当。结果表明，咪唑核心是抗菌试验中的药效团。

  DOI：

  10.1007/s11094-022-02622-1
• 作为产物：
  描述：

  Ethyl 2-bromo-5-methylfuran-3-carboxylate 在 lithium aluminium tetrahydride 、 水 、 氯化铵 、 吡啶 、 氯化亚砜 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 生成 4-(chloromethyl)-2-methylfuran 、 2-bromo-5-methyl-3-(chloromethyl)furan
  参考文献：
  名称：

  Synthesis of isomeric bromo(diethoxyphosphorylmethyl)furans

  摘要：

  Series of the previously unknown bromo(diethoxyphosphorylmethyl)furans including four of six possible regioisomers is synthesized. The target products were obtained by bromination of the corresponding (diethoxyphosphorylmethyl)furans or by a four-step synthesis including bromination of isomeric methyl-furancarboxylates, reduction of the products formed to the corresponding alcohols, substitution of hydroxy group with halogen and phosphorylation by the Michaelis-Becker reaction. It was established for the first fime that in the course of bromination of alkyl carboxylates and phosphonates of the furan series under the typical conditions of electrophilic reaction (Br(2) + 10% molar of AlCl(3), chloroform) the substituent enters not only into the heteroring, but also into the side chain. In the case of 5-methyl-2-(diethoxyphosphorylmethyl)furan only the last reaction pathway is observed. It is shown that bromo(chloromethyl)furans react with sodium diethyl phosphite not only according to the Michaelis-Becker scheme leading to phosphonates, but also by the pathway of debromination of the furan ring. The last unexpected reaction may acquire a practical use for removing a substituent protecting the alpha-position of the furan ring under mild conditions.

  DOI：

  10.1134/s1070363209030050

文献信息

• Synthesis of isomeric bromo(diethoxyphosphorylmethyl)furans
  作者：L. M. Pevzner

  DOI：10.1134/s1070363209030050

  日期：2009.3

  Series of the previously unknown bromo(diethoxyphosphorylmethyl)furans including four of six possible regioisomers is synthesized. The target products were obtained by bromination of the corresponding (diethoxyphosphorylmethyl)furans or by a four-step synthesis including bromination of isomeric methyl-furancarboxylates, reduction of the products formed to the corresponding alcohols, substitution of hydroxy group with halogen and phosphorylation by the Michaelis-Becker reaction. It was established for the first fime that in the course of bromination of alkyl carboxylates and phosphonates of the furan series under the typical conditions of electrophilic reaction (Br(2) + 10% molar of AlCl(3), chloroform) the substituent enters not only into the heteroring, but also into the side chain. In the case of 5-methyl-2-(diethoxyphosphorylmethyl)furan only the last reaction pathway is observed. It is shown that bromo(chloromethyl)furans react with sodium diethyl phosphite not only according to the Michaelis-Becker scheme leading to phosphonates, but also by the pathway of debromination of the furan ring. The last unexpected reaction may acquire a practical use for removing a substituent protecting the alpha-position of the furan ring under mild conditions.
• Synthesis of Heterocyclic Systems 3H-furo[2,3-b]imidazo[4,5-f]quinolines and 3H-furo[2,3-b]pyrazolo[4,3-f]quinolines as New Antibacterial Agents
  作者：Maryam Rangamiz Toosi、Mehdi Pordel、Mohammad Reza Bozorgmehr

  DOI：10.1007/s11094-022-02622-1

  日期：2022.5

  need to find new antibiotic compounds is increasing due to the growing antibiotic resistant bacteria. In this study, some new 3H-furo[2,3-b]imidazo[4,5-f]quinolines and 3H-furo-[2,3-b]pyrazolo[4,3-f]quinolines were obtained from the reaction of 1-alkyl-5-nitro-1H-benzoimidazoles and 1-alkyl-5-nitro-1H-indazoles with 2-(5-methylfuran-2-yl)acetonitrile in high yields. The structures of the new compounds

  随着当前的挑战，由于抗生素耐药性细菌的增长，寻找新的抗生素化合物的需求也在增加。本研究获得了一些新的3 H-呋喃[2,3- b ]咪唑并[4,5- f ]喹啉和3 H-呋喃-[2,3- b ]吡唑并[4,3- f ]喹啉1-烷基-5-硝基-1 H-苯并咪唑和1-烷基-5-硝基-1 H-吲唑与2-(5-甲基呋喃-2-基)乙腈以高产率反应。新化合物的结构通过光谱(FT-IR, 1 H NMR, 13C NMR）和分析数据。抗菌筛选表明，标题化合物对革兰氏阳性菌和革兰氏阴性菌均非常有效，其 MIC 值与氨苄青霉素、青霉素 G 和磺胺甲恶唑等知名抗菌剂相当。结果表明，咪唑核心是抗菌试验中的药效团。