(±)-(5S,7R,9S)-7,9-bis(3-nitrophenyl)-1,6,8-trioxaspiro[4.5]dec-3-en-2-one

• 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: (±)-(5S,7R,9S)-7,9-bis(3-nitrophenyl)-1,6,8-trioxaspiro[4.5]dec-3-en-2-one
• 英文别名: (5S,7S,9R)-7,9-bis(3-nitrophenyl)-1,8,10-trioxaspiro[4.5]dec-3-en-2-one
• 化学式: C₁₉H₁₄N₂O₈
• 分子量: 398.329
• InChiKey: FLEOSTSYCZZYFX-UHOSZYNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (±)-(5S,7R,9S)-7,9-bis(3-nitrophenyl)-1,6,8-trioxaspiro[4.5]dec-3-en-2-one 、 苯甲醛 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以16%的产率得到(±)-(5S,7R,9S)-9-(3-nitrophenyl)-7-phenyl-1,6,8-trioxaspiro[4.5]dec-3-en-2-one
  参考文献：
  名称：

  Acid-mediated coupling of γ-hydroxybutenolides and aldehydes: synthesis of a new class of spirocyclic ketal-lactones

  摘要：

  In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf), gamma-methyl-gamma-hydroxybutenolide reacts with aromatic aldehydes to generate a new class of stereochemically rich spirocyclic ketal-lactones in good yields and with excellent stereoselectivities. We believe that this process takes place through the in situ generation of protoanemonin followed by a Prins reaction. Herein, we describe this discovery, along with substrate scope and preliminary mechanistic studies. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.139
• 作为产物：
  描述：

  5-hydroxy-5-methyl-2(5H)-furanone 、 间硝基苯甲醛 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以90%的产率得到(±)-(5S,7R,9S)-7,9-bis(3-nitrophenyl)-1,6,8-trioxaspiro[4.5]dec-3-en-2-one
  参考文献：
  名称：

  Acid-mediated coupling of γ-hydroxybutenolides and aldehydes: synthesis of a new class of spirocyclic ketal-lactones

  摘要：

  In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf), gamma-methyl-gamma-hydroxybutenolide reacts with aromatic aldehydes to generate a new class of stereochemically rich spirocyclic ketal-lactones in good yields and with excellent stereoselectivities. We believe that this process takes place through the in situ generation of protoanemonin followed by a Prins reaction. Herein, we describe this discovery, along with substrate scope and preliminary mechanistic studies. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.139

文献信息

• Acid-mediated coupling of γ-hydroxybutenolides and aldehydes: synthesis of a new class of spirocyclic ketal-lactones
  作者：Alberto Munoz、Ryan P. Murelli

  DOI：10.1016/j.tetlet.2012.09.139

  日期：2012.12

  In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf), gamma-methyl-gamma-hydroxybutenolide reacts with aromatic aldehydes to generate a new class of stereochemically rich spirocyclic ketal-lactones in good yields and with excellent stereoselectivities. We believe that this process takes place through the in situ generation of protoanemonin followed by a Prins reaction. Herein, we describe this discovery, along with substrate scope and preliminary mechanistic studies. (C) 2012 Elsevier Ltd. All rights reserved.