Trifluoro-methanesulfonic acid 3-(3-furan-2-yl-3-oxo-propyl)-6-methyl-2-oxo-2H-pyran-4-yl ester | 206257-42-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Trifluoro-methanesulfonic acid 3-(3-furan-2-yl-3-oxo-propyl)-6-methyl-2-oxo-2H-pyran-4-yl ester
• CAS: 206257-42-3
• 化学式: C₁₄H₁₁F₃O₇S
• 分子量: 380.298
• InChiKey: PKTSSOJUJBKJQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  103.79
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1S,2S)-1,2-dibenzylethyleneglycol 、 Trifluoro-methanesulfonic acid 3-(3-furan-2-yl-3-oxo-propyl)-6-methyl-2-oxo-2H-pyran-4-yl ester 在 对甲苯磺酸 作用下， 以79%的产率得到
  参考文献：
  名称：

  Diastereocontrol in [4+4]-photocycloadditions of pyran-2-ones: effect of ring substituents and chiral ketal

  摘要：

  4-Mesyloxypyran-2-ones joined to furan by a three-carbon linker undergo intramolecular-crossed [4+4]-photocycloaddition with high or complete selectivity for the exo cycloadcluct. When a C-2-symmetric ketal was present on the tether adjacent to the pyranone ring, moderate levels of asymmetric induction were obtained. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.117
• 作为产物：
  描述：

  三氟甲磺酸酐 、 3-(3-(furan-2-yl)-3-oxopropyl)-4-hydroxy-6-methyl-2H-pyran-2-one 在 三乙胺 作用下， 以80%的产率得到Trifluoro-methanesulfonic acid 3-(3-furan-2-yl-3-oxo-propyl)-6-methyl-2-oxo-2H-pyran-4-yl ester
  参考文献：
  名称：

  Diastereocontrol in [4+4]-photocycloadditions of pyran-2-ones: effect of ring substituents and chiral ketal

  摘要：

  4-Mesyloxypyran-2-ones joined to furan by a three-carbon linker undergo intramolecular-crossed [4+4]-photocycloaddition with high or complete selectivity for the exo cycloadcluct. When a C-2-symmetric ketal was present on the tether adjacent to the pyranone ring, moderate levels of asymmetric induction were obtained. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.117

文献信息

• 1,3-Dioxolan-2-ylium cations from acylfurans: Conversion of furyl ketones to esters under nonoxidative conditions
  作者：John A. Bender、Samantha Daves、F.G. West

  DOI：10.1016/s0040-4039(98)00185-3

  日期：1998.4

  Acylfurans 3 furnished tosylated glycol monoesters 5 when treated with 1,2-diols in the presence of an equivalent of TsOH. This process likely occurs via protiodefuranation of the intermediate furyl ketals to form 1,3-dioxolan-2-ylium cations 8. Subsequent ring-opening via SN2 nucleophilic displacement by p-toluenesulfonate then provides esters 5. When a 1,3-diol was employed, furan-containing ester

  当在等价的TsOH存在下用1,2-二醇处理时，酰基呋喃3提供了甲苯磺酸化的二醇单酯5。此过程可能通过中间呋喃基缩酮的Protoodefuranation形成1，3-dioxolan-2-ylium阳离子8发生。随后通过对甲苯磺酸的S N 2亲核取代而开环，然后提供酯5。当使用1，3-二醇时，通过表观的醇醛二聚/片段化途径形成了含呋喃的酯9而不是标准产物。