2-Methylsulfanyl-5-(1-prop-2-ynyloxy-cyclohexyl)-furan | 153758-92-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-Methylsulfanyl-5-(1-prop-2-ynyloxy-cyclohexyl)-furan
• 英文别名: 2-Methylsulfanyl-5-(1-prop-2-ynoxycyclohexyl)furan
• CAS: 153758-92-0
• 化学式: C₁₄H₁₈O₂S
• 分子量: 250.362
• InChiKey: LBTJUNFSRIEYLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Methylsulfanyl-5-(1-prop-2-ynyloxy-cyclohexyl)-furan 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-Methanesulfonyl-5-(1-prop-2-ynyloxy-cyclohexyl)-furan
  参考文献：
  名称：

  Intramolecular Diels−Alder Reaction of Furans with Allenyl Ethers Followed by Sulfur and Silicon Atom-Containing Group Rearrangement

  摘要：

  The intramolecular Diels-Alder reactions of a furandiene with an allenyl ether dienophile followed by the alkylthio, alkylsulfinyl, alkylsulfonyl, and trimethylsilyl group rearrangements are reported. Refluxing the propargyl ether 3 with t-BuOK in t-BuOH at 85 degrees C gave the 1,4-rearrangement product 4 exclusively. The alkylthio group 1,4-rearrangement may proceed intramolecularly via the tight; ion pairs. Refluxing the 5-(alkylsulfinyl)-2-furfuryl propargyl ethers 9a-e and the 5-(alkylsulfonyl)-2-furfuryl propargyl ethers 19a-e under the same reaction conditions gave the alkylsulfinyl group and the alkylsulfonyl group 1,2-rearrangement products 10a-e and 20a-e, respectively. No detectable amount of the corresponding 1,4-rearrangement products 11a-e and 21a-e was obtained. In the cases of 9b and 19b, which possess two furfurylic hydrogen atoms, no detectable amount of the furan ring-transfer reaction products was obtained. Refluxing the 5-(trimethylsilyl)-2-furfuryl propargyl ethers 25a-d with t-BuOK in t-BuOH at 85 degrees C for 10 h gave the trimethylsilyl group 1,2-rearrangement products 26a-d and Brook rearrangement products 27a-d. The reaction mechanisms for these novel intramolecular Diels-Alder reactions are discussed. In the case of 37, which possesses two furfurylic hydrogen atoms, compound 38 was obtained via an intramolecular Diels-Alder reaction followed by the furan ring-transfer reaction and Brook rearrangement.

  DOI：

  10.1021/jo980240l
• 作为产物：
  描述：

  2-(methylsulfanyl)-furan 在 正丁基锂 作用下， 以 四氢呋喃 、 二甲基亚砜 、 苯 为溶剂， 反应 10.0h， 生成 2-Methylsulfanyl-5-(1-prop-2-ynyloxy-cyclohexyl)-furan
  参考文献：
  名称：

  Study on the reaction mechanism of the base-catalyzed intramolecular Diels-Alder reaction of furfuryl propargyl ethers

  摘要：

  DOI：

  10.1021/jo00124a033

文献信息

• Intramolecular Diels-Alder reaction of furans with allenyl ethers followed by methylthio group 1,4-rearrangement
  作者：Hsien-Jen Wu、Wei-Dar Shao、Fu-Hsing Ying

  DOI：10.1016/s0040-4039(00)75802-3

  日期：1994.1

  The base-catalyzed intramolecular Diels-Alder reactions of the furfuryl propargyl ethers 1a–1e gave compounds 6a–6e as the major product respectively, a novel reaction involving an intramolecular Diels-Alder reaction followed by a methylthio group 1,4-rearrangement.

  糠基炔丙基醚1a-1e的碱催化的分子内Diels-Alder反应分别得到化合物6a-6e作为主要产物，该反应涉及分子内的Diels-Alder反应，然后是甲硫基1,4-重排。
• Intramolecular Diels−Alder Reaction of Furans with Allenyl Ethers Followed by Sulfur and Silicon Atom-Containing Group Rearrangement
  作者：Hsien-Jen Wu、Chia-Hui Yen、Chi-Te Chuang

  DOI：10.1021/jo980240l

  日期：1998.7.1

  The intramolecular Diels-Alder reactions of a furandiene with an allenyl ether dienophile followed by the alkylthio, alkylsulfinyl, alkylsulfonyl, and trimethylsilyl group rearrangements are reported. Refluxing the propargyl ether 3 with t-BuOK in t-BuOH at 85 degrees C gave the 1,4-rearrangement product 4 exclusively. The alkylthio group 1,4-rearrangement may proceed intramolecularly via the tight; ion pairs. Refluxing the 5-(alkylsulfinyl)-2-furfuryl propargyl ethers 9a-e and the 5-(alkylsulfonyl)-2-furfuryl propargyl ethers 19a-e under the same reaction conditions gave the alkylsulfinyl group and the alkylsulfonyl group 1,2-rearrangement products 10a-e and 20a-e, respectively. No detectable amount of the corresponding 1,4-rearrangement products 11a-e and 21a-e was obtained. In the cases of 9b and 19b, which possess two furfurylic hydrogen atoms, no detectable amount of the furan ring-transfer reaction products was obtained. Refluxing the 5-(trimethylsilyl)-2-furfuryl propargyl ethers 25a-d with t-BuOK in t-BuOH at 85 degrees C for 10 h gave the trimethylsilyl group 1,2-rearrangement products 26a-d and Brook rearrangement products 27a-d. The reaction mechanisms for these novel intramolecular Diels-Alder reactions are discussed. In the case of 37, which possesses two furfurylic hydrogen atoms, compound 38 was obtained via an intramolecular Diels-Alder reaction followed by the furan ring-transfer reaction and Brook rearrangement.
• Study on the reaction mechanism of the base-catalyzed intramolecular Diels-Alder reaction of furfuryl propargyl ethers
  作者：Hsien-Jen Wu、Fu-Hsing Ying、Wei-Dar Shao

  DOI：10.1021/jo00124a033

  日期：1995.9