rac-(1R,1'R,3')-1',3'-dihydrospiro[indene-2,1'-isobenzofuran]-3-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: rac-(1R,1'R,3')-1',3'-dihydrospiro[indene-2,1'-isobenzofuran]-3-one
• 英文别名: (3R,3'R)-1,3'-dihydroxyspiro[1H-2-benzofuran-3,2'-3H-indene]-1'-one
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: MPFLXGAEOBOYBE-YAELJHOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  rac-(1R,1'R,3')-1',3'-dihydrospiro[indene-2,1'-isobenzofuran]-3-one 、 三甲基乙酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以73%的产率得到[(1R,1'R,3R)-1'-hydroxy-3'-oxospiro[1H-2-benzofuran-3,2'-1H-indene]-1-yl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  N-Heterocyclic Carbene Catalyzed Reaction of Phthalaldehydes: Controllable Stereoselective Synthesis of Polyhydroxylated Spiro- and Fused Indenones Dictated by the Structure of NHC Catalysts

  摘要：

  The N-heterocyclic carbene catalyzed stereoselective dimerization reactions of phthalaldehydes produced polyhydroxylated spiro- or fused indenones. The reaction pathways were dictated by the structures of NHC catalysts. Under the catalysis of a imidazole carbene, phthalaldehydes produced dihydroxylspiro[indene-2,1'-isobenzofuran]-3-ones in good to excellent yields, whereas a triazole carbene catalyzed reaction of phthalaldehydes afforded fully cis-trihydroxylindeno[2,1-a]inden-5-ones in high yields. This work not only provides a highly efficient method for the construction of valuable polyhydroxyl substituted indene derivatives that are not easily assembled by other synthetic means but also reflects the versatility of organocatalysis using N-heterocyclic carbenes.

  DOI：

  10.1021/jo102582a
• 作为产物：
  描述：

  邻苯二甲醛 在 (S)-2-benzyl-5-((tert-butyldiphenylsilyloxy)methyl)-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.08h， 生成 rac-(1R,1'R,3')-1',3'-dihydrospiro[indene-2,1'-isobenzofuran]-3-one
  参考文献：
  名称：

  通过多米诺·斯特特-阿尔多-迈克尔和斯特特-阿尔多-阿尔多反应合成螺双-茚满：范围和局限性

  摘要：

  据报道，通过N-杂环卡宾（NHC）催化合成螺双茚满。在噻唑鎓衍生的卡宾催化下，各种邻甲酰基查尔酮底物的二聚化或它们与邻苯二甲醛衍生物的结合分别提供了Stetter-aldol-Michael产品和Stetter-aldol-aldol产品。将不良的迈克尔受体与N-烷基三唑鎓衍生的催化剂结合使用可提供多种二苯并[8]环戊烯产品。这项工作强调了影响NHC催化的多米诺骨牌反应中竞争途径的多种因素之间的相互作用。 NHC-有机催化-斯特特-物质保护-多米诺反应-迈克尔-奥尔多

  DOI：

  10.1055/s-0030-1260031

文献信息

• <i>N</i>-Heterocyclic Carbene Catalyzed Reaction of Phthalaldehydes: Controllable Stereoselective Synthesis of Polyhydroxylated Spiro- and Fused Indenones Dictated by the Structure of NHC Catalysts
  作者：Ying Cheng、Jiang-Hua Peng、Yong-Jia Li、Xun-Yu Shi、Ming-Sheng Tang、Tian-Yu Tan

  DOI：10.1021/jo102582a

  日期：2011.3.18

  The N-heterocyclic carbene catalyzed stereoselective dimerization reactions of phthalaldehydes produced polyhydroxylated spiro- or fused indenones. The reaction pathways were dictated by the structures of NHC catalysts. Under the catalysis of a imidazole carbene, phthalaldehydes produced dihydroxylspiro[indene-2,1'-isobenzofuran]-3-ones in good to excellent yields, whereas a triazole carbene catalyzed reaction of phthalaldehydes afforded fully cis-trihydroxylindeno[2,1-a]inden-5-ones in high yields. This work not only provides a highly efficient method for the construction of valuable polyhydroxyl substituted indene derivatives that are not easily assembled by other synthetic means but also reflects the versatility of organocatalysis using N-heterocyclic carbenes.
• Synthesis of Spiro Bis-Indanes via Domino Stetter-Aldol-Michael and Stetter-Aldol-Aldol Reactions: Scope and Limitations
  作者：Michel Gravel、Eduardo Sánchez-Larios、Janice Holmes、Crystal Daschner

  DOI：10.1055/s-0030-1260031

  日期：2011.6

  The synthesis of spiro bis-indanes by means of N-heterocyclic carbene (NHC) catalysis is reported. The dimerization of various o-formylchalcone substrates or their combination with phthaldialdehyde derivatives under the catalysis of thiazolium-derived­ carbenes afforded Stetter-aldol-Michael products and Stetter­-aldol-aldol products, respectively. The use of poor Michael acceptors in conjunction with

  据报道，通过N-杂环卡宾（NHC）催化合成螺双茚满。在噻唑鎓衍生的卡宾催化下，各种邻甲酰基查尔酮底物的二聚化或它们与邻苯二甲醛衍生物的结合分别提供了Stetter-aldol-Michael产品和Stetter-aldol-aldol产品。将不良的迈克尔受体与N-烷基三唑鎓衍生的催化剂结合使用可提供多种二苯并[8]环戊烯产品。这项工作强调了影响NHC催化的多米诺骨牌反应中竞争途径的多种因素之间的相互作用。 NHC-有机催化-斯特特-物质保护-多米诺反应-迈克尔-奥尔多