3-hydroxy-2,5,5-trimethylcyclohex-1-en-1-yl trifluoromethanesulfonate | 1448520-98-6

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 3-hydroxy-2,5,5-trimethylcyclohex-1-en-1-yl trifluoromethanesulfonate
• CAS: 1448520-98-6
• 化学式: C₁₀H₁₅F₃O₄S
• 分子量: 288.288
• InChiKey: VKFUVMCHBXGLLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  磷酰基乙酸三乙酯 、 3-hydroxy-2,5,5-trimethylcyclohex-1-en-1-yl trifluoromethanesulfonate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.83h， 以94%的产率得到(E)-ethyl 5,5-dimethylnon-2-en-7-ynoate
  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：

  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

文献信息

• Reaction Discovery Using Neopentylene-Tethered Coupling Partners: Cycloisomerization/Oxidation of Electron-Deficient Dienynes
  作者：Nicholas J. Kramer、Tung T. Hoang、Gregory B. Dudley

  DOI：10.1021/acs.orglett.7b02261

  日期：2017.9.1

  A rhodium-catalyzed cycloisomerization and oxidation of tethered dienynes for the synthesis of indanes is described. An auxiliary fragmentation/olefination method (also described herein) provides novel access to tethered alkyne-dienoate substrates. The reported method circumvents current limitations in and expands the scope of inverse-demand Diels–Alder-type cycloadditions. Traditional discovery substrates

  描述了铑催化的环二烯异构化和拴系二烯的氧化，用于合成茚满。辅助的裂解/烯烃化方法（也在本文中进行了描述）提供了对拴系的炔-二烯二酸酯底物的新颖访问。报道的方法规避了当前的局限性，并扩大了反需求Diels-Alder型环加成反应的范围。在当前方法中，涉及基于丙二酸酯，醚和磺酰胺基系链的传统发现底物是有问题的，强调了新戊二烯系链的底物在反应发现中的独特优势。