(3S,6'R)-1-methyl-6'-phenylspiro[indole-3,2'-oxane]-2,4'-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (3S,6'R)-1-methyl-6'-phenylspiro[indole-3,2'-oxane]-2,4'-dione
• 化学式: C₁₉H₁₇NO₃
• 分子量: 307.349
• InChiKey: SDCPKMGKYPQCCX-MJGOQNOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-(2-hydroxy-2-phenylethyl)-2,2-dimethyl-4H-1,3-dioxin-4-one 在 三氟甲磺酸 、 二甲基亚砜 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 26.5h， 生成 (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

文献信息

• Oxa-Diels–Alder Reaction of Isatins and Acyclic α,β-Unsaturated Methyl Ketones through Cooperative Dienamine and Metal Lewis Acid Catalysis
  作者：Hong Wang、Lu Liu、Philias Daka、Ryan Sarkisian、Yongming Deng、Kraig Wheeler

  DOI：10.1055/s-0033-1338613

  日期：——

  Abstract Cooperative enamine and metal Lewis acid catalysis was applied to develop an asymmetric oxa-Diels–Alder reaction of isatins and but-3-en-2-ones. Spirooxindole tetrahydropyranones were obtained in good yields (58–86%), moderate stereoselectivities (1.3:1–5.9:1 dr, 50–81% ee), and excellent chemoselectivity. Cooperative enamine and metal Lewis acid catalysis was applied to develop an asymmetric

  摘要 烯胺和金属路易斯酸的协同催化作用被用于开发靛红和3-3-烯-2-酮的不对称oxa-Diels-Alder反应。吡咯并吲哚四氢吡喃酮的收率高（58–86％），立体选择性适中（1.3：1–5.9：1 dr，50–81％ee），并且具有出色的化学选择性。 烯胺和金属路易斯酸的协同催化作用被用于开发靛红和3-3-烯-2-酮的不对称oxa-Diels-Alder反应。吡咯并吲哚四氢吡喃酮的收率高（58–86％），立体选择性适中（1.3：1–5.9：1 dr，50–81％ee），并且具有出色的化学选择性。
• 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.