3,4-dibromo-2-(5-methyl-2-propan-2-ylcyclohexyl)oxy-2H-furan-5-one | 819849-44-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,4-dibromo-2-(5-methyl-2-propan-2-ylcyclohexyl)oxy-2H-furan-5-one
• CAS: 819849-44-0
• 化学式: C₁₄H₂₀Br₂O₃
• 分子量: 396.119
• InChiKey: WIPMONFGSJSSTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-dibromo-2-(5-methyl-2-propan-2-ylcyclohexyl)oxy-2H-furan-5-one 、 potassium thioacyanate 在 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 32.0h， 以68%的产率得到3-bromo-5-menthoxy-4-thiocyanatofuran-2(5H)-one
  参考文献：
  名称：

  通过3,4-二卤代-2（5H）-呋喃酮进行C4选择性合成乙烯基硫氰酸酯和硒代氰酸酯

  摘要：

  环保协议允许在没有金属催化剂的情况下并在简单的促进下，由3,4-二卤代-2（5 H）-呋喃酮（包括低反应性Csp2-Cl），底物来合成硫氰酸乙烯酯和硒代氰酸酯无机碱碳酸氢钠。

  DOI：

  10.1002/ejoc.201900749
• 作为产物：
  描述：

  3,4-二溴-5-羟基呋喃-2(5h)-酮 、 薄荷脑 生成 3,4-dibromo-2-(5-methyl-2-propan-2-ylcyclohexyl)oxy-2H-furan-5-one
  参考文献：
  名称：

  3,4-Dihalo-2(5H)-furanones: a novel oxidant for the Glaser coupling reaction

  摘要：

  5-Alkoxy-3,4-dihalo-2(5H)-furanones could be used as a kind of novel oxidant in the Glaser coupling reaction. The screening of reaction conditions showed that both PdCl2(PPh3)(2) and 3,4-dichloro-5-methoxy-2(5H)-furanone played crucial roles in the reaction. A possible reaction mechanism was proposed according to the reactivity of 3,4-dihalo-2(5H)-furanones. The new method easily allows the syntheses of alkyl and aryl substituted 1,3-diyne compounds. However, carbyne polymer was unexpectedly obtained when using trimethylsilyl acetylene as the substrate under the Glaser reaction condition.

  DOI：

  10.1007/s00706-011-0479-5

文献信息

• 3,4-Dihalo-2(5H)-furanones: a novel oxidant for the Glaser coupling reaction
  作者：Jian-Xiao Li、Hao-Ran Liang、Zhao-Yang Wang、Jian-Hua Fu

  DOI：10.1007/s00706-011-0479-5

  日期：2011.5

  5-Alkoxy-3,4-dihalo-2(5H)-furanones could be used as a kind of novel oxidant in the Glaser coupling reaction. The screening of reaction conditions showed that both PdCl2(PPh3)(2) and 3,4-dichloro-5-methoxy-2(5H)-furanone played crucial roles in the reaction. A possible reaction mechanism was proposed according to the reactivity of 3,4-dihalo-2(5H)-furanones. The new method easily allows the syntheses of alkyl and aryl substituted 1,3-diyne compounds. However, carbyne polymer was unexpectedly obtained when using trimethylsilyl acetylene as the substrate under the Glaser reaction condition.
• C4-Selective Synthesis of Vinyl Thiocyanates and Selenocyanates Through 3,4-Dihalo-2(5<i>H</i> )-furanones
  作者：Han-Qing Wu、Kai Yang、Shi-He Luo、Xin-Yan Wu、Neng Wang、Si-Hong Chen、Zhao-Yang Wang

  DOI：10.1002/ejoc.201900749

  日期：2019.7.31

  An environmental‐friendly protocol enables the synthesis of vinyl thiocyanates and selenocyanates from 3,4‐dihalo‐2(5H)‐furanones, including low‐reactive Csp2‐Cl, substrates in the absence of a metal catalyst and under the promotion of simple inorganic base sodium bicarbonate.

  环保协议允许在没有金属催化剂的情况下并在简单的促进下，由3,4-二卤代-2（5 H）-呋喃酮（包括低反应性Csp2-Cl），底物来合成硫氰酸乙烯酯和硒代氰酸酯无机碱碳酸氢钠。