(E)-crotyl 2-thiophenemethyl ether | 881168-53-2

• 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: (E)-crotyl 2-thiophenemethyl ether
• 英文别名: 2-[[(E)-but-2-enoxy]methyl]thiophene
• CAS: 881168-53-2
• 化学式: C₉H₁₂OS
• 分子量: 168.26
• InChiKey: BBAUPZHWMVSLBW-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-crotyl 2-thiophenemethyl ether 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 1.0h， 生成 (E)-2-(2-hydroxy-3-penten-1-yl)thiophene 、 2-(1-hydroxy-2-methyl-3-buten-1-yl)thiophene 、 (E)-3-(1-hydroxy-2-buten-1-yl)-2-methylthiophene
  参考文献：
  名称：

  Wittig Rearrangement of Ally 2-Thiophenemethyl Ethers: Facile Synthesis of Thiophenemethanol and -ethanol Derivatives

  摘要：

  Wittig rearrangement of allyl 2-thiophenemethyl ethers was studied. Deprotonation of allyl 2-thiophenemethyl ethers (1a-d) occurred preferentially either the alpha- or the alpha'-position, depending on three kinds of BuLi. Thiophenemethanol and -ethanol derivatives were obtained as products of [2,31 and [1,2] sigmatropic rearrangements, respectively.

  DOI：

  10.3987/com-05-s(k)5
• 作为产物：
  描述：

  2-噻吩甲醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以60%的产率得到(E)-crotyl 2-thiophenemethyl ether
  参考文献：
  名称：

  Wittig Rearrangement of Ally 2-Thiophenemethyl Ethers: Facile Synthesis of Thiophenemethanol and -ethanol Derivatives

  摘要：

  Wittig rearrangement of allyl 2-thiophenemethyl ethers was studied. Deprotonation of allyl 2-thiophenemethyl ethers (1a-d) occurred preferentially either the alpha- or the alpha'-position, depending on three kinds of BuLi. Thiophenemethanol and -ethanol derivatives were obtained as products of [2,31 and [1,2] sigmatropic rearrangements, respectively.

  DOI：

  10.3987/com-05-s(k)5

文献信息

• Wittig Rearrangement of Ally 2-Thiophenemethyl Ethers: Facile Synthesis of Thiophenemethanol and -ethanol Derivatives
  作者：Masayoshi Tsubuki、Toshio Honda、Sohichiro Matsuo

  DOI：10.3987/com-05-s(k)5

  日期：——

  Wittig rearrangement of allyl 2-thiophenemethyl ethers was studied. Deprotonation of allyl 2-thiophenemethyl ethers (1a-d) occurred preferentially either the alpha- or the alpha'-position, depending on three kinds of BuLi. Thiophenemethanol and -ethanol derivatives were obtained as products of [2,31 and [1,2] sigmatropic rearrangements, respectively.