dimethyl 3,4,5,6-tetraphenylphthalate | 752-01-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl 3,4,5,6-tetraphenylphthalate
• 英文别名: dimethyl-3,4,5,6-tetraphenyl-1,2-phenylenedicarboxylate；dimethyl 3,4,5,6-tetraphenylbenzene-1,2-dicarboxylate；dimethyl tetraphenylphthalate；tetraphenyl-phthalic acid dimethyl ester；Tetraphenyl-phthalsaeure-dimethylester；1,2,3,4-Tetraphenyl-5,6-bis-(carbomethoxy)-benzol；[1,1':2',1''-Terphenyl]-3',4'-dicarboxylic acid, 5',6'-diphenyl-, dimethyl ester
• CAS: 752-01-2
• 化学式: C₃₄H₂₆O₄
• 分子量: 498.578
• InChiKey: JKLYQGQCMNPZSJ-UHFFFAOYSA-N

物化性质

• 熔点：
  250-251 °C
• 沸点：
  600.5±55.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  dimethyl 3,4,5,6-tetraphenylphthalate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 1,2-bis(hydroxymethyl)-3,4,5,6-tetraphenylbenzene
  参考文献：
  名称：

  Probing Intramolecular CH−π Interactions in o-Quinodimethane Adducts of [60]Fullerene Using Variable Temperature NMR

  摘要：

  Several o-quinodimethane adducts of [60]fullerene were synthesized and their intramolecular aryl CH-fullerene pi interactions were studied using variable temperature-NMR (VT-NMR). Evaluation of the rate constants associated with the first-order transition states for cyclohexene boat-to-boat inversions enables quantification of Delta G(double dagger) values for each inversion. A comparison between two constitutional isomers, only one of which is capable of intramolecular CH-pi interactions, provides a lower limit of 0.95 kcal/mol for each aryl CH-fullerene pi interaction.

  DOI：

  10.1021/jo201921h
• 作为产物：
  描述：

  四苯基邻苯二甲酸酐 在 甲醇 、 氢氧化钾 、 乙醚 作用下， 生成 dimethyl 3,4,5,6-tetraphenylphthalate
  参考文献：
  名称：

  Dilthey; Thewalt; Troesken, Chemische Berichte, 1934, vol. 67, p. 1959,1963

  摘要：

  DOI：

文献信息

• Cycloaddition of thiophene S-oxides to allenes, alkynes and to benzyne
  作者：Thies Thiemann、Hideki Fujii、Daisuke Ohira、Kazuya Arima、Yuanqiang Li、Shuntaro Mataka

  DOI：10.1039/b303091c

  日期：——

  the presence of m-chloroperoxybenzoic acid to give substituted arenes as cycloadducts. Alternatively, thiophene S-oxides have been prepared by oxidation from thiophenes and have been subjected to cycloaddition with alkynes in a subsequent step. The outcome of the reaction is dependent on the steric demand of the thiophene S-oxide. Some thiophene S-oxides can be reacted at temperatures as high as 140°C

  噻吩已经与在存在炔处理米氯过氧酸，得到取代的芳烃如cycloadducts。另外，噻吩S-氧化物是通过从噻吩氧化制得的，并在随后的步骤中与炔烃进行环加成反应。反应的结果取决于噻吩S-氧化物的空间需求。某些噻吩S-氧化物可以在高达140 °C的温度下反应而不会分解。噻吩作为脱氧产物是主要的副产物。噻吩S-氧化物与丙二烯的反应部分产生12a型噻双环[2.2.1]庚烯S-氧化物和13以及加香的产品。噻吩S-氧化物也环加成苯并。
• Studies on organogermanium heterocycles and related compounds
  作者：N.K. Hota、C.J. Willis

  DOI：10.1016/s0022-328x(00)86327-5

  日期：1968.11

  Attempts to synthesize fluorinated heterocycles containing germanium are described. 1,1-Dimethyl-2,3,4,5-tetraphenyl-1-germacyclopentadiene has been prepared, but did not undergo simple Diels-Alder addition to various acetylenes to give isolable germanorbornadienes. The analogous silicon heterocycle underwent ready addition to hexafluoro-2-butyne to give the trifluoromethyl-substituted silanorbornadiene

  描述了合成含锗的氟化杂环的尝试。已经制备了1，1-二甲基-2，3，4，5-四苯基-1-锗环戊二烯，但是没有对各种乙炔进行简单的Diels-Alder加成反应以得到可分离的锗烷降冰片二烯。立即将类似的硅杂环加到六氟-2-丁炔中，得到三氟甲基取代的硅烷基降冰片二烯。
• Organic chemistry of subvalent transition metal complexes
  作者：John J. Eisch、James.E. Galle、Allen A. Aradi、Marek P. Bolesa̵wski

  DOI：10.1016/0022-328x(86)80327-8

  日期：1986.10

  and heat displays the properties of a nickelole, rather than a cyclobutadienenickel(0) complex. Attempts to generate IIIb photochemically from η4-1,5-cyclooctadiene(η4-tetraphenylcyclopentadienone)nickel and diphos failed, but it was shown that structural types, such as η4-tetraphenyl-cyclopentadienone(diphos)nickel (a model for the structure suggested by Hoberg and Richter for IIIb), are unstable.

  由（E，E基）-1,2,3,4-四苯基-1,3-丁二烯-1,4- ylidenedilithium（I）和相应的镍（Ⅱ）氯化物-膦配合物（II）或从η的降低4 -tetraphenylcyclobutadienenickel（ II）在膦存在下的溴化物二聚体（XII），收率高。镍三烯IIIa具有与其结构一致的物理和化学性质，并且是二苯乙炔三聚化的催化剂。镍三烯IIIb是高度缔合的结构，但对炔烃，HOAc，O 2，Br 2，NaAlEt 2的化学反应H 2和热量显示了镍烯而不是环丁二烯镍（0）配合物的性质。试图产生IIIb族光化学从η 4 -1,5-环辛二烯（η 4 -tetraphenylcyclopentadienone）镍和DIPHOS失败了，但它表明结构类型，如η 4四苯基环戊二烯酮（DIPHOS）镍（对于一个模型Hoberg和Richter对于IIIb）提出的结构是不稳定的。
• ISOBENZOFURANE, A TRANSIENT INTERMEDIATE
  作者：Louis F. Fieser、Makhluf J. Haddadin

  DOI：10.1139/v65-211

  日期：1965.5.1

  A study of Diels–Alder reactions of tetraphenylcyclopentadienone (II) coupled with development of two improved procedures for the generation of benzyne, one of which affords a practical route to the reactive dienophile 1,4-dihydronaphthalene-1,4-endo-oxide (Ia), led to an investigation of the reaction of Ia and II. At 80° these reactants combine readily to give the adduct IIIa, which is cleaved on pyrolysis to isobenzofurane VIIIa and 1,2,3,4-tetraphenylbenzene (IX). The transient existence of isobenzofurane (VIIIa) was established by trapping it with the 1,4-endo-oxide Ia and isolation of the adducts X and XI. In confirmation of the interpretation, X and XI were obtained by independent synthesis from the adduct Va from Ia and α-pyrone and thermal decomposition of Va in the presence of Ia as trapping agent. Parallel experiments with 1,4-dimethyl-1,4-dihydronaphthalene-1,4-endo-oxide, as well as mixed additions, supported the interpretations advanced. Evidence is presented to show that isobenzofurane (VIIIa) invariably adds exo to the bicyclic dienophile.

  一项关于四苯基环戊二烯酮（II）的Diels-Alder反应研究，结合了两种改进的苯基生成方法，其中一种提供了一条实用的途径到反应性双烯丙烯1,4-二氢萘-1,4-内氧化物（Ia），导致对Ia和II的反应进行研究。在80°C下，这些反应物很容易结合形成加合物IIIa，经热解裂解为异苯并呋喃醚VIIIa和1,2,3,4-四苯基苯（IX）。通过与1,4-内氧化物Ia的捕获和加合物X和XI的分离，已经确定了异苯并呋喃醚（VIIIa）的短暂存在。通过与1,4-二甲基-1,4-二氢萘-1,4-内氧化物以及混合加成的平行实验，支持了提出的解释。提供了证据表明异苯并呋喃醚（VIIIa）总是朝向双环双烯丙烯的exo位置进行加成。
• Diphosphan-tetraphenylnickelacyclopentadien
  作者：Heinz Hoberg、Wolfgang Richter

  DOI：10.1016/s0022-328x(00)93319-9

  日期：1980.8

  Reaction of 1,2-bis(diorganophosphino)ethanenickel dibromide (I) with 1,2,3,4-tetraphenyl-1,4-dilithiumbutadiene (II) at −30°C yields diphosphannickelacyclopentadiene (III) which at elevated temperatures isomerizes to diphosphanecyclobutadienenickel(0) (IV). The thermodynamic and kinetic parameters of the rearrangement were determined. The structural and conformational analyses of III were carried

  1,2-双（二有机膦基）乙烷二溴化镍（I）与1,2,3,4-四苯基-1,4-二锂丁二烯（II）在-30°C下反应生成二磷烷基镍环戊二烯（III），在高温下异构化为二膦环丁二烯镍（0）（IV）。确定了重排的热力学和动力学参数。III的结构和构象分析是通过13 C NMR，31 P NMR和拉曼光谱法进行的。III和IV与CH 3 COOH，CO，RCCR和RNCNR的反应已被氨化，并讨论了所观察到的反应性III IIIIV。