1,4-diphenyl-1,4-epoxy-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylic anhydride

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: 1,4-diphenyl-1,4-epoxy-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylic anhydride
• 英文别名: (1R,8S,9S,13R)-1,8-diphenyl-11,14-dioxatetracyclo[6.5.1.02,7.09,13]tetradeca-2,4,6-triene-10,12-dione
• 化学式: C₂₄H₁₆O₄
• 分子量: 368.389
• InChiKey: LXGWNCJNLUFEQL-XZOTUCIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,4-diphenyl-1,4-epoxy-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylic anhydride 在 溶剂黄146 作用下， 以 氘代甲醇 、 二氯甲烷-D2 为溶剂， 反应 24.5h， 生成
  参考文献：
  名称：

  Measurement of Silver−π Interactions in Solution Using Molecular Torsion Balances

  摘要：

  A new series of molecular torsion balances were designed to measure the strength of individual Ag-pi interactions in solution for an Ag(I) coordinated to a pyridine nitrogen. The formation of a well-defined intramolecular Ag-pi interaction in these model systems was verified by X-ray crystallography and H-1 NMR. The strength of the intramolecular Ag-pi interaction in solution was found to be stabilizing in nature and quantified to be -1.34 to -2.63 kcal/mol using a double mutant cycle analysis. The Ag-pi interaction was also found to be very sensitive to changes in geometry or solvent environment.

  DOI：

  10.1021/jacs.5b04554
• 作为产物：
  描述：

  马来酸酐 、 1,3-二苯基异苯并呋喃 在 乙酸乙酯 作用下， 反应 0.03h， 以100%的产率得到1,4-diphenyl-1,4-epoxy-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylic anhydride
  参考文献：
  名称：

  机械化学研磨 Diels-Alder 反应：高效快速地获得双环、三环和四环系统

  摘要：

  在无催化剂和无溶剂的条件下，在研杵和研钵中用不同的二烯研磨各种缺电子的亲二烯体 1-15 分钟，得到相应的 Diels-Alder 加合物，在无催化剂和无溶剂的条件下，无需任何纯化步骤。

  DOI：

  10.1055/s-0036-1558970

文献信息

• Distance‐Dependent Attractive and Repulsive Interactions of Bulky Alkyl Groups
  作者：Jungwun Hwang、Ping Li、Mark D. Smith、Ken D. Shimizu

  DOI：10.1002/anie.201602752

  日期：2016.7.4

  meta‐position, smaller groups were stabilizing and larger groups were destabilizing. Conversely, at the farther para‐position, the larger alkyl groups were systematically more stabilizing with the bulky tBu group forming the strongest stabilizing interaction. X‐ray crystal structures showed that the stabilizing interactions of the small meta‐alkyl and large para‐alkyl groups were due to their similar

  在溶液中通过实验测量了烷基对芳族堆积相互作用的稳定和去稳定作用。在设计用于测量分子内芳族相互作用强度的分子平衡模型系统中，烷基的大小（Me，Et，i Pr和t Bu）和位置（间位和对位）有所不同。在芳环上不同位置的烷基取代基观察到相反的稳定性趋势。在越接近元位上，更小的组被稳定和较大的组均不稳定。相反，在较远的对位上，较大的烷基基团进行了系统的多用笨重稳定吨卜基形成最强的稳定相互作用。X射线晶体结构表明，较小的间烷基和较大的对烷基的稳定相互作用是由于它们的相近距离以及与相对芳环边缘的范德华接触面积所致。
• Additivity of Substituent Effects in Aromatic Stacking Interactions
  作者：Jungwun Hwang、Ping Li、William R. Carroll、Mark D. Smith、Perry J. Pellechia、Ken D. Shimizu

  DOI：10.1021/ja504378p

  日期：2014.10.8

  predict SEs with an accuracy from ±0.01 to ±0.02 kcal/mol. The additive SEs were consistent with Wheeler and Houk's direct SE model. However, the indirect or polarization SE model cannot be ruled out as it shows similar levels of additivity for two to three substituent systems, which were the number of substituents in our model system. SE additivity also has practical utility as the SEs can be accurately

  本研究的目的是通过实验测试静电取代基效应 (SE) 对芳烃堆积相互作用的可加性。使用可以采用偏移面对面芳香堆积几何结构的小分子模型系统评估 SE 的可加性。这些分子扭转平衡的分子内相互作用通过折叠/展开构象平衡的变化进行定量测量。检查了五种不同类型的取代基（CH3、OCH3、Cl、CN 和 NO2），范围从给电子到吸电子。测量了氯仿溶液中 21 个取代芳烃堆积天平和 21 个对照天平的分子内堆积相互作用的强度。观察到的稳定性趋势与添加剂 SE 一致。具体来说，附加 SE 模型可以以 ±0.01 到 ±0.02 kcal/mol 的精度预测 SE。附加 SE 与 Wheeler 和 Houk 的直接 SE 模型一致。然而，不能排除间接或极化 SE 模型，因为它显示了两到三个取代基系统的相似水平的可加性，这是我们模型系统中取代基的数量。SE 可加性也具有实际效用，因为可以准确预测 SE。这应该
• A Molecular Balance for Measuring Aliphatic CH−π Interactions
  作者：William R. Carroll、Chen Zhao、Mark D. Smith、Perry J. Pellechia、Ken D. Shimizu

  DOI：10.1021/ol201657p

  日期：2011.8.19

  A series of conformationally flexible bicyclic N-arylimides were employed as molecular balances to study the weak aliphatic CH-pi Interaction between alkyl and arene groups. The formation of intramolecular CH-pi interactions in the folded conformers was characterized by X-ray crystallography. The strengths of the interactions were characterized in CDCl(3) by the changes in the folded/unfolded ratios, as measured by (1)H NMR. The CH-pi interaction between a methyl group and an aromatic surface was similar to 1.0 kcal/mol and was easily disrupted or masked by conformational entropy and repulsive steric Interactions.
• Badri, Rashid; Heidarizadeh, Fariba, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 5, p. 1000 - 1003
  作者：Badri, Rashid、Heidarizadeh, Fariba

  DOI：——

  日期：——
• Do Deuteriums Form Stronger CH−π Interactions?
  作者：Chen Zhao、Robert M. Parrish、Mark D. Smith、Perry J. Pellechia、C. David Sherrill、Ken D. Shimizu

  DOI：10.1021/ja305788p

  日期：2012.9.5

  The D/H isotope effect for the CH-pi interaction was studied experimentally and computationally. First, a series of molecular balances that are very sensitive to changes in the strength of the CH-pi interactions in solution were designed. Balances with deuterated and non-deuterated alkyl groups were synthesized, and their intramolecular CH-pi interactions were compared. The geometries of their intramolecular CH-pi and CD-pi interactions were characterized in the solid state by X-ray analysis, and the strength of each interaction was characterized in solution by the folded/unfolded ratio as measured by H-1 NMR spectra. Second, the relative strengths of the CH-pi and CD-pi interactions were also assessed computationally using dispersion-corrected DFT (PDE-D2/6-31+G*). No significant differencee was observed in either the experimental or theoretical studies, indicating that the D/H isotope effect for the CH-pi interaction is either very small or nonexistent.