3-[2-(2-[1,3]Dioxan-2-yl-ethyl)-[1,3]dithian-2-yl]-cyclopentanone | 167101-23-7

• 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: 3-[2-(2-[1,3]Dioxan-2-yl-ethyl)-[1,3]dithian-2-yl]-cyclopentanone
• 英文别名: 3-[2-[2-(1,3-Dioxan-2-yl)ethyl]-1,3-dithian-2-yl]cyclopentan-1-one
• CAS: 167101-23-7
• 化学式: C₁₅H₂₄O₃S₂
• 分子量: 316.486
• InChiKey: YDOSEKIGHXLWDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  86.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[2-(2-[1,3]Dioxan-2-yl-ethyl)-[1,3]dithian-2-yl]-cyclopentanone 在 对甲苯磺酸 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 copper(l) iodide 、 ammonium cerium(IV) nitrate 、 L-Selectride 、 potassium carbonate 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 、 苯 为溶剂， 反应 36.3h， 生成 [(1R,7R)-2,2,7-trimethyl-4-oxo-3,5,6,7-tetrahydro-1H-inden-1-yl] methanesulfonate
  参考文献：
  名称：

  A Stereoselective Total Synthesis of (.+-.)-Alliacol A and Congeners of Marasmius Alliaceus

  摘要：

  Synthesis of alliacolide(1), alliacol A (2), and 12-noralliacolide (4), members of the alliacane family of sesquiterpene lactones, was accomplished through both syn- and anti-modes of intramolecular S-N' displacement. Two routes to 12-noralliacolide (4) are presented, which contrast brevity and efficiency in stereoselection (i.e. 14 --> 16/17 versus 37a/b --> 38). Since both routes culminate in C-ring annulation, introduction of the correct stereochemical arrangement relied heavily on the structural features of the hydrindane (AB) precursor(s). Choice of the proper AB system 24 facilitated production of tetrahydrofuran 38. With the full skeleton in place, 38 was efficiently epoxidized and oxidized to 4. 12-Noralliacolide (4) served as an appropriate relay substrate for conversion to alliacol A (2) and several other alliacanes.

  DOI：

  10.1021/jo00120a027
• 作为产物：
  描述：

  2-环戊烯酮 、 2-<3,3-(propylenedioxy)propyl>-1,3-dithiane 在 正丁基锂 作用下， 以77%的产率得到3-[2-(2-[1,3]Dioxan-2-yl-ethyl)-[1,3]dithian-2-yl]-cyclopentanone
  参考文献：
  名称：

  A Stereoselective Total Synthesis of (.+-.)-Alliacol A and Congeners of Marasmius Alliaceus

  摘要：

  Synthesis of alliacolide(1), alliacol A (2), and 12-noralliacolide (4), members of the alliacane family of sesquiterpene lactones, was accomplished through both syn- and anti-modes of intramolecular S-N' displacement. Two routes to 12-noralliacolide (4) are presented, which contrast brevity and efficiency in stereoselection (i.e. 14 --> 16/17 versus 37a/b --> 38). Since both routes culminate in C-ring annulation, introduction of the correct stereochemical arrangement relied heavily on the structural features of the hydrindane (AB) precursor(s). Choice of the proper AB system 24 facilitated production of tetrahydrofuran 38. With the full skeleton in place, 38 was efficiently epoxidized and oxidized to 4. 12-Noralliacolide (4) served as an appropriate relay substrate for conversion to alliacol A (2) and several other alliacanes.

  DOI：

  10.1021/jo00120a027

文献信息

• A Stereoselective Total Synthesis of (.+-.)-Alliacol A and Congeners of Marasmius Alliaceus
  作者：James J. La Clair、Peter T. Lansbury、Ben-xin Zhi、Karst Hoogsteen

  DOI：10.1021/jo00120a027

  日期：1995.7

  Synthesis of alliacolide(1), alliacol A (2), and 12-noralliacolide (4), members of the alliacane family of sesquiterpene lactones, was accomplished through both syn- and anti-modes of intramolecular S-N' displacement. Two routes to 12-noralliacolide (4) are presented, which contrast brevity and efficiency in stereoselection (i.e. 14 --> 16/17 versus 37a/b --> 38). Since both routes culminate in C-ring annulation, introduction of the correct stereochemical arrangement relied heavily on the structural features of the hydrindane (AB) precursor(s). Choice of the proper AB system 24 facilitated production of tetrahydrofuran 38. With the full skeleton in place, 38 was efficiently epoxidized and oxidized to 4. 12-Noralliacolide (4) served as an appropriate relay substrate for conversion to alliacol A (2) and several other alliacanes.