(3,7'-cis)-1,2',2'-trimethyl-7'-phenyl-7',8'-dihydro-4'Hspiro[indoline-3,5'-pyrano[4,3-d][1,3]dioxine]-2,4'-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (3,7'-cis)-1,2',2'-trimethyl-7'-phenyl-7',8'-dihydro-4'Hspiro[indoline-3,5'-pyrano[4,3-d][1,3]dioxine]-2,4'-dione
• 英文别名: (5S,7S)-1',2,2-trimethyl-7-phenylspiro[7,8-dihydropyrano[4,3-d][1,3]dioxine-5,3'-indole]-2',4-dione
• 化学式: C₂₃H₂₁NO₅
• 分子量: 391.423
• InChiKey: UIOYPALBCZNAKH-SBUREZEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3,7'-cis)-1,2',2'-trimethyl-7'-phenyl-7',8'-dihydro-4'Hspiro[indoline-3,5'-pyrano[4,3-d][1,3]dioxine]-2,4'-dione 在 二甲基亚砜 作用下， 以 水 为溶剂， 反应 24.0h， 以93%的产率得到(3S,6'R)-1-methyl-6'-phenylspiro[indole-3,2'-oxane]-2,4'-dione
  参考文献：
  名称：

  Highly Stereoselective Brønsted Acid Catalyzed Synthesis of Spirooxindole Pyrans

  摘要：

  A Bronsted acid-catalyzed Prins-type cyclization sequence to construct spirooxindole pyrans in high yields and excellent diastereoselectivity has been developed. The combination of a beta-hydroxy dioxinone fragment and isatin dimethyl acetal generate oxa-spirooxindoles efficiently. These compounds are diversifiable scaffolds that tap into the rich chemistry of dioxinones.

  DOI：

  10.1021/ol200987c
• 作为产物：
  描述：

  (3,3-dimethoxy-N-methyl)indoline-2-one 、 6-(2-hydroxy-2-phenylethyl)-2,2-dimethyl-4H-1,3-dioxin-4-one 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以81%的产率得到(3,7'-cis)-1,2',2'-trimethyl-7'-phenyl-7',8'-dihydro-4'Hspiro[indoline-3,5'-pyrano[4,3-d][1,3]dioxine]-2,4'-dione
  参考文献：
  名称：

  Highly Stereoselective Brønsted Acid Catalyzed Synthesis of Spirooxindole Pyrans

  摘要：

  A Bronsted acid-catalyzed Prins-type cyclization sequence to construct spirooxindole pyrans in high yields and excellent diastereoselectivity has been developed. The combination of a beta-hydroxy dioxinone fragment and isatin dimethyl acetal generate oxa-spirooxindoles efficiently. These compounds are diversifiable scaffolds that tap into the rich chemistry of dioxinones.

  DOI：

  10.1021/ol200987c

文献信息

• Highly Stereoselective Brønsted Acid Catalyzed Synthesis of Spirooxindole Pyrans
  作者：Jingqi Wang、Erika A. Crane、Karl A. Scheidt

  DOI：10.1021/ol200987c

  日期：2011.6.17

  A Bronsted acid-catalyzed Prins-type cyclization sequence to construct spirooxindole pyrans in high yields and excellent diastereoselectivity has been developed. The combination of a beta-hydroxy dioxinone fragment and isatin dimethyl acetal generate oxa-spirooxindoles efficiently. These compounds are diversifiable scaffolds that tap into the rich chemistry of dioxinones.