(R)-5-deutero-2-phenyl-2,3-dihydrofuran

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-5-deutero-2-phenyl-2,3-dihydrofuran
• 英文别名: (2R)-5-deuterio-2-phenyl-2,3-dihydrofuran
• 化学式: C₁₀H₁₀O
• 分子量: 147.181
• InChiKey: PQHIJMWKRKSDNQ-ORKHTJSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,2-dideutero-2,3-dihydrofuran 、 苯基三氟甲烷磺酸酯 在 palladium diacetate (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 、 N,N-二异丙基乙胺 作用下， 以 苯 为溶剂， 反应 24.0h， 生成 (R)-5-deutero-2-phenyl-2,3-dihydrofuran 、 (S)-5-deutero-2-phenyl-2,3-dihydrofuran 、 (S)-5,5-dideutero-2-phenyl-2,5-dihydrofuran 、 (R)-5,5-dideutero-2-phenyl-2,5-dihydrofuran
  参考文献：
  名称：

  Use of Deuterium Labeling Studies to Determine the Stereochemical Outcome of Palladium Migrations during an Asymmetric Intermolecular Heck Reaction

  摘要：

  [GRAPHICS]A series of deuterium labeling experiments showed that Pd migrations during an intermolecular asymmetric Heck reaction between phenyl triflate and various deuterated 2,3-dihydrofurans (2b, 2c, 2d, 2e) occurs exclusively by either syn-1,2-dyotropic shifts or a syn-chain-walking mechanism; no evidence was observed to support anti-1,2-dyotropic shifts or anti-beta-H Pd eliminations during the formation of 6 and 7.

  DOI：

  10.1021/jo071119u

文献信息

• Use of Deuterium Labeling Studies to Determine the Stereochemical Outcome of Palladium Migrations during an Asymmetric Intermolecular Heck Reaction
  作者：Bronwen M. M. Wheatley、Brian A. Keay

  DOI：10.1021/jo071119u

  日期：2007.9.1

  [GRAPHICS]A series of deuterium labeling experiments showed that Pd migrations during an intermolecular asymmetric Heck reaction between phenyl triflate and various deuterated 2,3-dihydrofurans (2b, 2c, 2d, 2e) occurs exclusively by either syn-1,2-dyotropic shifts or a syn-chain-walking mechanism; no evidence was observed to support anti-1,2-dyotropic shifts or anti-beta-H Pd eliminations during the formation of 6 and 7.