1-Allyloxymethyl-4,8-dithia-spiro[2.5]octane | 264599-40-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 1-Allyloxymethyl-4,8-dithia-spiro[2.5]octane
• 英文别名: 2-(Prop-2-enoxymethyl)-4,8-dithiaspiro[2.5]octane
• CAS: 264599-40-8
• 化学式: C₁₀H₁₆OS₂
• 分子量: 216.368
• InChiKey: CGKXGRGATSYMCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Allyloxymethyl-4,8-dithia-spiro[2.5]octane 在 iron(III) perchlorate 1,3-二噻烷 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以68%的产率得到(3aS,6aR)-spiro[1,3,3a,4,6,6a-hexahydrocyclopenta[c]furan-5,2'-1,3-dithiane]
  参考文献：
  名称：

  Fe(III)-Catalyzed Radical Cyclization of Cyclopropanone Thioacetal

  摘要：

  DOI：

  10.3987/com-99-s48
• 作为产物：
  描述：

  (rac)-2-[1,3]dithian-2-ylmethyl-oxirane 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 1-Allyloxymethyl-4,8-dithia-spiro[2.5]octane
  参考文献：
  名称：

  Fe(III)-Catalyzed Radical Cyclization of Cyclopropanone Thioacetal

  摘要：

  DOI：

  10.3987/com-99-s48

文献信息

• Development of Solvent-Driven Iron-Catalyzed Reactions
  作者：Toshiyuki Itoh

  DOI：10.3987/rev-16-842

  日期：——

  The possibility of solvent-driven iron-catalyzed reactions has been investigated using ionic liquids and acetonitrile as key solvents. Three iron-catalyzed reactions, the intramolecular cyclization of cyclopropane dithioacetals, the [2+2]-cycloaddition of (trans)-anethole, and the [2+3]-type cycloaddition of styrene derivatives with 1,4-benzoquinone, were first developed using acetonitrile as solvent in the presence of 3 similar to 5 mol% of Fe(ClO4)(3)center dot Al2O3 or Fe(BF4)(2)center dot 6H(2)O under air conditions. In particular, we found the rapid cycloaddition of iron-catalyzed [2+3]-type cycloaddition of styrene derivatives with 1,4-benzoquinone when the reaction was carried out in an ionic liquid which contained [PF6] or [Tf2N] anion. Homo-coupling reaction of aryl or alkynyl Grignard reagent was next discovered using 1 mol% of FeCl3 as catalyst and the reaction also proceeded very rapidly in an ionic liquid. We also found that 3-5 mol% of Fe(ClO4)(2)center dot Al2O3 or Fe(BF4)(2)center dot 6H(2)O-successfully catalyzed Friedel-Crafts type alkylation of indoles or pyrroles with vinyl ketones or alpha-aryl-beta-silylalcohol. In particular, the reaction of chiral alpha-aryl-beta-silylalcohol with indole using Fe(ClO4)(3)center dot nH(2)O as catalyst proceeded with retention of the configuration of stereochemistry of the hydroxyl group. Then, we discovered the first example of iron-catalyzed enantioselective C-S bond formation via Michael addition of thiols to (E)-3-crotonoyloxazolidin-2-one using 10 mol% of Fe(BF4)(2)/Pybox. We further demonstrated that Fe(ClO4)(3)center dot Al2O3-catalyzed the Nazarov type cyclizations of thiophene, pyrrole, indole, benzofuran, and benzo[b]thiophene derivatives using ionic liquids as solvent. Solvents have been recognized as a by-player in chemical reactions in the process of "optimization of reaction conditions". However, further investigation of the solvent-driven iron-catalyzed reaction will allow discovery of useful reactions for organic syntheses.