2,5,5-trimethyl-3-oxocyclohex-1-en-1-yl trifluoromethanesulfonate | 1236191-13-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 2,5,5-trimethyl-3-oxocyclohex-1-en-1-yl trifluoromethanesulfonate
• 英文别名: (2,5,5-Trimethyl-3-oxocyclohexen-1-yl) trifluoromethanesulfonate；(2,5,5-trimethyl-3-oxocyclohexen-1-yl) trifluoromethanesulfonate
• CAS: 1236191-13-1
• 化学式: C₁₀H₁₃F₃O₄S
• 分子量: 286.272
• InChiKey: QDNRKDNWRRJDMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,5,5-trimethyl-3-oxocyclohex-1-en-1-yl trifluoromethanesulfonate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.83h， 以100%的产率得到3-hydroxy-2,5,5-trimethylcyclohex-1-en-1-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis of High-Value 1,6-Enynes by Tandem Fragmentation/Olefination

  摘要：

  A tandem process provides high-value 1,6-enynes that are otherwise difficult to prepare. Two base-mediated reactions-fragmentation and olefination-are executed in a coordinated manner that is overall more efficient than either reaction on its own. The 1,6-enynes can be strategically employed in conjunction with carbocyclization to deliver important targets, as noted for reported syntheses of hirsutene and illudol.

  DOI：

  10.1021/ol401839e
• 作为产物：
  描述：

  三氟甲磺酸酐 、 2,5,5-三甲基环己烷-1,3-二酮 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.34h， 以100%的产率得到2,5,5-trimethyl-3-oxocyclohex-1-en-1-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis of High-Value 1,6-Enynes by Tandem Fragmentation/Olefination

  摘要：

  A tandem process provides high-value 1,6-enynes that are otherwise difficult to prepare. Two base-mediated reactions-fragmentation and olefination-are executed in a coordinated manner that is overall more efficient than either reaction on its own. The 1,6-enynes can be strategically employed in conjunction with carbocyclization to deliver important targets, as noted for reported syntheses of hirsutene and illudol.

  DOI：

  10.1021/ol401839e

文献信息

• An open-and-shut strategy: preparation of benzo-fused indanes by ring-opening of a vinylogous acyl triflate and metal-catalyzed Asao–Yamamoto benzannulation
  作者：David M. Jones、Gregory B. Dudley

  DOI：10.1016/j.tet.2010.03.014

  日期：2010.6

  A two-step strategy for the synthesis of benzo-fused indanes is outlined herein. The strategy draws on two independent methodologies: the tandem addition/fragmentation of vinylogous acyl triflates (VATs) and the intramolecular benzannulation of o-alkynylphenyl ketones. Reduction of this strategy to practice involves the use of aryltriazenes as masked aryl iodides; a synthetic equivalent of 2-iodophenyllithium is featured. Benzo-fused indanes are prepared efficiently and in high yield. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of High-Value 1,6-Enynes by Tandem Fragmentation/Olefination
  作者：Tung T. Hoang、Gregory B. Dudley

  DOI：10.1021/ol401839e

  日期：2013.8.2

  A tandem process provides high-value 1,6-enynes that are otherwise difficult to prepare. Two base-mediated reactions-fragmentation and olefination-are executed in a coordinated manner that is overall more efficient than either reaction on its own. The 1,6-enynes can be strategically employed in conjunction with carbocyclization to deliver important targets, as noted for reported syntheses of hirsutene and illudol.