diisopropyl 2,3-dihydro-5-methyl-1H-indene-3a,7a-dicarboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diisopropyl 2,3-dihydro-5-methyl-1H-indene-3a,7a-dicarboxylate
• 英文别名: diisopropyl cis-5-methyl-2,3-dihydro-1H-indene-3a,7a-dicarboxylate；dipropan-2-yl (3aR,7aS)-5-methyl-2,3-dihydro-1H-indene-3a,7a-dicarboxylate
• 化学式: C₁₈H₂₆O₄
• 分子量: 306.402
• InChiKey: LFCQVOVSVIYFSS-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diisopropyl 2,3-dihydro-5-methyl-1H-indene-3a,7a-dicarboxylate 在 萘 、 potassium diazodicarboxylate 、 lithium 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.02h， 生成 diisopropyl (Z)-7-methylcyclonon-6-ene-1,5-dicarboxylate
  参考文献：
  名称：

  A Two-Step, Stereoselective Synthesis of Nine- and Ten-Membered Carbocycles from Phthalates

  摘要：

  A two-step, stereoselective procedure for the synthesis of nine- and ten-membered carbocycles from readily available phthalates is described. A variety of dialkyl phthalates have been transformed into [6,n]-fused bicyclo systems (n = 5, 6, 7) by a dearomatization/cyclization process and then converted into cyclonona- and cyclodecadienes through a bond cleavage reaction, whereby both processes are promoted by alkaline metals in THF.

  DOI：

  10.1021/acs.orglett.5b00552
• 作为产物：
  描述：

  4-甲基邻苯二甲酸 在 4-二甲氨基吡啶 、 萘 、 sodium 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 diisopropyl 2,3-dihydro-5-methyl-1H-indene-3a,7a-dicarboxylate
  参考文献：
  名称：

  A Two-Step, Stereoselective Synthesis of Nine- and Ten-Membered Carbocycles from Phthalates

  摘要：

  A two-step, stereoselective procedure for the synthesis of nine- and ten-membered carbocycles from readily available phthalates is described. A variety of dialkyl phthalates have been transformed into [6,n]-fused bicyclo systems (n = 5, 6, 7) by a dearomatization/cyclization process and then converted into cyclonona- and cyclodecadienes through a bond cleavage reaction, whereby both processes are promoted by alkaline metals in THF.

  DOI：

  10.1021/acs.orglett.5b00552

文献信息

• Dearomatization−Bis-alkylation of Aromatic and Heteroaromatic Diesters Promoted by Me₃SnLi via a Stanna−Brook Rearrangement
  作者：Pablo Monje、Paula Graña、M. Rita Paleo、F. Javier Sardina

  DOI：10.1021/ol053130r

  日期：2006.3.2

  Reaction of Me3SnLi with aromatic and heteroaromatic diesters proceeds through a fast stanna-Brook rearrangement that generates an stable bis-enolate which can be regioselectively alkylated and cyclized, in one step, to bicyclic compounds containing 6,5-, 6,6-, and 6,7-fused ring systems.

  Me3SnLi与芳族和杂芳族二酯的反应通过快速的stanna-Brook重排进行，该重排生成稳定的双烯酸酯，该双烯酸酯可在一个区域内进行区域选择性烷基化和环化，生成含6,5-，6,6-和6-环戊二烯的双环化合物6,7稠环系统。
• Enantioselective Annulation Reactions of Bisenolates Prepared Through Dearomatization Reactions of Aromatic and Heteroaromatic Diesters
  作者：Jaime Pérez-Vázquez、Alberte X. Veiga、Gustavo Prado、F. Javier Sardina、M. Rita Paleo

  DOI：10.1002/ejoc.201101427

  日期：2012.2

  A one-pot, enantioselective strategy for the dearomatization–annulation of aromatic diesters to give a range of highly functionalized polycyclic molecules with excellent enantioselectivity is presented. This methodology is based on the reaction of bisenolates, prepared by treating aromatic diesters with trialkyltin lithium reagents, which involves a stanna-Brook rearrangement, with 1,ω-dihaloalkanes

  提出了一种用于芳族二酯脱芳构化-环化的单锅对映选择性策略，以提供一系列具有优异对映选择性的高度官能化多环分子。该方法基于双烯醇盐的反应，通过用三烷基锡锂试剂处理芳族二酯制备，该反应涉及 stanna-Brook 重排，与 1,ω-二卤代烷烃和其他双亲电子试剂。我们还开发了实验条件，通过将 Me6Sn2 原位回收到含有过量锂金属的 Me3SnLi 中，用亚化学计量的所需锡试剂进行这些反应，并提供了对这种合成方法的范围和局限性的研究。