indacene-2,2,7,7-tetracarboxylic acid 1,3,6,8-tetrahydrotetraethyl ester | 142835-58-3

• 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: indacene-2,2,7,7-tetracarboxylic acid 1,3,6,8-tetrahydrotetraethyl ester
• 英文别名: 1,3,6,8-tetrahydro-as-indacene-2,2,7,7-tetracarboxylic acid tetraethyl ester；Tetraethyl 1,3,6,8-tetrahydro-as-indacene-2,2,7,7-tetracarboxylate
• CAS: 142835-58-3
• 化学式: C₂₄H₃₀O₈
• 分子量: 446.497
• InChiKey: IVWLMGASWUSSNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  indacene-2,2,7,7-tetracarboxylic acid 1,3,6,8-tetrahydrotetraethyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以18%的产率得到(2,7,7-Tris-hydroxymethyl-1,2,3,6,7,8-hexahydro-as-indacen-2-yl)-methanol
  参考文献：
  名称：

  New Spirans Containing a 1,5-Benzodithiepine System, Derived from Methylbenzenes. Conformational Transmission

  摘要：

  [GRAPHICS]A synthesis of three new spirans, derived from methylbenzenes, containing the 1,5-benzodithiepine system is reported. X-ray structure proved the identity of model monospiran 9. In the solid and liquid state, the conformation of the seven membered ring is chair, and the five-membered ring has the envelope conformation. The effect of conformational transmission in spirans 9 and 10 was observed, The synthesis of trispirans from hexamethylbenzene using the proposed scheme is also possible.

  DOI：

  10.1021/ol990335p
• 作为产物：
  描述：

  四甲基萘 在 N-溴代丁二酰亚胺(NBS) 作用下， 生成 indacene-2,2,7,7-tetracarboxylic acid 1,3,6,8-tetrahydrotetraethyl ester
  参考文献：
  名称：

  New Spirans Containing a 1,5-Benzodithiepine System, Derived from Methylbenzenes. Conformational Transmission

  摘要：

  [GRAPHICS]A synthesis of three new spirans, derived from methylbenzenes, containing the 1,5-benzodithiepine system is reported. X-ray structure proved the identity of model monospiran 9. In the solid and liquid state, the conformation of the seven membered ring is chair, and the five-membered ring has the envelope conformation. The effect of conformational transmission in spirans 9 and 10 was observed, The synthesis of trispirans from hexamethylbenzene using the proposed scheme is also possible.

  DOI：

  10.1021/ol990335p

文献信息

• Air-Stable {(C₅H₅)Co} Catalysts for [2+2+2] Cycloadditions
  作者：Anaïs Geny、Nicolas Agenet、Laura Iannazzo、Max Malacria、Corinne Aubert、Vincent Gandon

  DOI：10.1002/anie.200806001

  日期：2009.2.23

  Cobalt cyclopentadienyl complexes incorporating a fumarate and a CO ligand (see picture) efficiently catalyze inter‐ and intramolecular [2+2+2] cycloadditions of alkynes, nitriles, and/or alkenes to give benzenes, pyridines, or 1,3‐cyclohexadienes. Unlike catalysts such as [CpCo(CO)2] or [CpCo(C2H4)2] (Cp=C5H5), they are air‐stable, easy to handle, compatible with microwave conditions, and do not necessarily

  结合富马酸酯和CO配体的环戊二烯钴复合物（见图）有效地催化炔烃，腈和/或烯烃的分子间和分子内[2 + 2 + 2]环加成反应，从而生成苯，吡啶或1,3-环己二烯。与[CpCo（CO）2 ]或[CpCo（C 2 H 4）2 ]（Cp = C 5 H 5）等催化剂不同，它们具有空气稳定性，易于处理，与微波条件兼容，并且不一定需要辐射才能活跃。
• A Cheap Metal for a “Noble” Task:  Preparative and Mechanistic Aspects of Cycloisomerization and Cycloaddition Reactions Catalyzed by Low-Valent Iron Complexes
  作者：Alois Fürstner、Keisuke Majima、Rubén Martín、Helga Krause、Egmont Kattnig、Richard Goddard、Christian W. Lehmann

  DOI：10.1021/ja0777180

  日期：2008.2.1

  polyunsaturated substrates. The structures of ferrates 1 and 4 in the solid-state reveal the capacity of the reduced iron center to share electron density with the ligand sphere. This feature, coupled with the kinetic lability of the bound olefins, is thought to be responsible for the ease with which different enyne or diyne substrates undergo oxidative cyclization as the triggering event of the observed

  在乙烯或 COD 存在下，二茂铁与锂的反应允许大规模制备 Fe(0)-ate 络合物 1 和 4，结果证明它们是各种 Alder-ene 的优良催化剂，[4 +2]、[5+2] 和 [2+2+2] 环加成和多不饱和底物的环异构化反应。固态高铁酸盐 1 和 4 的结构揭示了还原铁中心与配体球共享电子密度的能力。这一特征与结合烯烃的动力学不稳定性相结合，被认为是不同烯炔或二炔底物易于氧化环化作为观察到的骨架重组的触发事件的原因。这种机械建议得到了高度指示性的氘标记实验的证实。而且，借助 Fe(+1) 配合物 6，可以拦截氧化环化歧管的两种不同产物，尽管其电子数为 17，但在某些情况下也具有催化能力。来自 6 和 tolane 的不寻常的环丁二烯配合物 38 用 X 射线晶体学表征。
• Cyclic cascade carbopalladation reactions as a route to benzene and fulvene derivatives
  作者：Ei-ichi Negishi、Lori S. Harring、Zbyslaw Owczarczyk、Mohamud M. Mohamud、Mehmet Ay

  DOI：10.1016/s0040-4039(00)92060-4

  日期：1992.6

  Palladium-catalyzed cyclization of appropriately structured triynes, haloalkenyldiynes, or haloalkenylalkyne-alkyne mixtures can provide the corresponding benzene derivatives, while the Pd-catalyzed intermolecular reaction of diynes with alkenyl halides can give fulvene derivatives.

  适当结构的三炔，卤代烯基二炔或卤代烯基炔烃-炔烃混合物的钯催化环化可提供相应的苯衍生物，而二炔与烯基卤化物的钯催化分子间反应可得到富烯衍生物。
• Reactive Dicarbon as a Flexible Ligand for Transition-Metal Coordination and Catalysis
  作者：Ming-Chun Wu、Yu-Fu Liang、Titel Jurca、Glenn P. A. Yap、Tsz-Fai Leung、Tiow-Gan Ong

  DOI：10.1021/jacs.2c05486

  日期：2022.7.20

  these molecules as a new complementary class of carbene-like ligands featuring strong σ-donor (>NHCs and CAAcs) but weak π-acceptor properties. Steric map analysis of PDC based on Cavallo’s SambVca program reveals comparable steric volume bulk of 32.5%, similar to the conventional IMes carbene. However, our PDCs exhibit dynamic steric flexibility modulated by the nature of the metal complexes and catalytic

  二碳是一种活性碳的同素异形体，天然仅存在于恒星空间的高温介质中。我们报告了一系列瓶装膦稳定二碳 (PDC) 分子的成功制备。我们探索将这些分子用作一类新的互补类卡宾配体，具有强 σ-供体（>NHCs 和 CAAcs）但弱 π-受体特性。基于 Cavallo 的 SambVca 程序的 PDC 空间图分析显示可比的空间体积体积为 32.5%，类似于传统的 IMes 卡宾。然而，我们的 PDC 表现出由金属配合物的性质和催化反应环境调节的动态空间柔性。我们通过成功实施 Suzuki-Miyaura 交叉偶联和醛和炔烃的还原偶联反应证明了 PDC 框架的催化效用。对还原偶联反应的详细研究揭示了 PDC 和金属配合物之间的重要二次相互作用，这在催化系统中起着至关重要的作用。
• Rhodium-Catalyzed Intramolecular Silylcarbotricyclization (SiCaT) of Triynes
  作者：Iwao Ojima、An T. Vu、James V. McCullagh、Atsushi Kinoshita

  DOI：10.1021/ja9815529

  日期：1999.4.1