trifluoromethanesulfonic acid 6-oxo-2-phenyl-3,6-dihydro-2H-pyran-4-yl ester | 1020850-69-4

• 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: trifluoromethanesulfonic acid 6-oxo-2-phenyl-3,6-dihydro-2H-pyran-4-yl ester
• 英文别名: (6-Oxo-2-phenyl-2,3-dihydropyran-4-yl) trifluoromethanesulfonate；(6-oxo-2-phenyl-2,3-dihydropyran-4-yl) trifluoromethanesulfonate
• CAS: 1020850-69-4
• 化学式: C₁₂H₉F₃O₅S
• 分子量: 322.262
• InChiKey: ZXAZQDCPZLABQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  trifluoromethanesulfonic acid 6-oxo-2-phenyl-3,6-dihydro-2H-pyran-4-yl ester 、 甲基溴化镁 以 乙醚 、 甲苯 为溶剂， 反应 1.0h， 以100%的产率得到1-苯基-3-丁炔-1-醇
  参考文献：
  名称：

  Ring Opening/Fragmentation of Dihydropyrones for the Synthesis of Homopropargyl Alcohols

  摘要：

  Ring-opening/C-C bond cleavage reactions induced by nucleophilic addition of methyl Grignard to 5,6-dihydro-2-pyrone (DHP) triflates 1 furnish homopropargyl alcohols (1 --> 2) stereospecifically with respect to the stereochemistry of 1. Carbonyl extrusion from DHP triflates provides a unified and operationally simple strategy for preparing chiral homopropargyl alcohols.

  DOI：

  10.1021/ja801018r
• 作为产物：
  描述：

  6-phenyldihydro-2H-pyran-2,4(3H)-dione 、 三氟甲磺酸酐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以96%的产率得到trifluoromethanesulfonic acid 6-oxo-2-phenyl-3,6-dihydro-2H-pyran-4-yl ester
  参考文献：
  名称：

  Ring Opening/Fragmentation of Dihydropyrones for the Synthesis of Homopropargyl Alcohols

  摘要：

  Ring-opening/C-C bond cleavage reactions induced by nucleophilic addition of methyl Grignard to 5,6-dihydro-2-pyrone (DHP) triflates 1 furnish homopropargyl alcohols (1 --> 2) stereospecifically with respect to the stereochemistry of 1. Carbonyl extrusion from DHP triflates provides a unified and operationally simple strategy for preparing chiral homopropargyl alcohols.

  DOI：

  10.1021/ja801018r

文献信息

• Achieving Vinylic Selectivity in Mizoroki-Heck Reaction of Cyclic Olefins
  作者：Xiaojin Wu、Yunpeng Lu、Hajime Hirao、Jianrong Steve Zhou

  DOI：10.1002/chem.201204427

  日期：2013.5.3

  In Heck reactions of cyclic olefins, the products usually have aryl groups that end up at the allylic and/or homoallylic position. We herein report new selectivity that adds aryl groups to the vinylic position. Cyclic olefins of various ring size worked well. The desired isomers were produced by palladium–hydride‐catalyzed isomerization of the initial products. Thus, a specific catalyst must be used

  在环烯烃的Heck反应中，产物通常具有芳基，该芳基最终在烯丙基和/或均烯丙基位置。我们在本文中报道了新的选择性，该选择性将芳基添加到乙烯基位置。各种环大小的环烯烃均能很好地发挥作用。所需的异构体是通过氢化钯催化的初始产物异构化反应制得的。因此，必须使用特定的催化剂，以使其可以在一组反应条件下进行两项工作。
• Ring Opening/Fragmentation of Dihydropyrones for the Synthesis of Homopropargyl Alcohols
  作者：Jumreang Tummatorn、Gregory B. Dudley

  DOI：10.1021/ja801018r

  日期：2008.4.1

  Ring-opening/C-C bond cleavage reactions induced by nucleophilic addition of methyl Grignard to 5,6-dihydro-2-pyrone (DHP) triflates 1 furnish homopropargyl alcohols (1 --> 2) stereospecifically with respect to the stereochemistry of 1. Carbonyl extrusion from DHP triflates provides a unified and operationally simple strategy for preparing chiral homopropargyl alcohols.