1,2,3,4-tetrakis(carbomethoxy)-5-methylbenzene | 101126-45-8

• 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: 1,2,3,4-tetrakis(carbomethoxy)-5-methylbenzene
• 英文别名: 2,3,4,5-tetrakis(carbomethoxy)-toluene；methyl-benzene-1,2,3,4-tetracarboxylic acid tetramethyl ester；Methyl-benzol-1,2,3,4-tetracarbonsaeure-tetramethylester；Methyl-benzol-1,2,3,4-tetracarbonsaeure；Tetramethyl 5-methylbenzene-1,2,3,4-tetracarboxylate
• CAS: 101126-45-8
• 化学式: C₁₅H₁₆O₈
• 分子量: 324.287
• InChiKey: OJBVYSOUCWXUAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  123-124 °C
• 沸点：
  362.2±37.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  对甲苯磺酸烯丙酯 、 丁炔二酸二甲酯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三苯基膦 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以41%的产率得到1,2,3,4-tetrakis(carbomethoxy)-5-methylbenzene
  参考文献：
  名称：

  通过pi-allpalladium中间体从炔烃和烯丙基甲苯磺酸盐中得到苯环

  摘要：

  [反应：参见正文]甲苯磺酸烯丙基酯是新型钯催化的苯环烷基化物的良好烯丙基来源，该苯环烷基化物由1摩尔的烯丙基化合物和2摩尔的内部炔烃提供多取代的苯。使用亚磷酸三苯酯作为配体，与末端炔烃的反应区域选择性地产生三取代的苯。

  DOI：

  10.1021/ol991406n

文献信息

• Air-tolerant C–C bond formation via organometallic ruthenium catalysis: diverse catalytic pathways involving (C5Me5)Ru or (C5H5)Ru are robust to molecular oxygen
  作者：Lukáš Severa、Jan Vávra、Anna Kohoutová、Martina Čížková、Tereza Šálová、Jakub Hývl、David Šaman、Radek Pohl、Louis Adriaenssens、Filip Teplý

  DOI：10.1016/j.tetlet.2009.05.079

  日期：2009.8

  carbon pronucleophiles, various [2+2+2] cycloadditions, and addition of a diazo compound to an alkyne are shown to proceed in the presence of air. Notably diverse catalytic manifolds remain supported under conditions generally regarded as prohibitive. Building on rare reports from the literature we show that a range of organometallic transformations based on reaction intermediates derived from (C5Me5)Ru

  碳原子亲核试剂的钌催化取代，各种[2 + 2 + 2]环加成反应以及重氮化合物向炔烃的加成反应均在空气存在下进行。值得注意的是，各种催化歧管在通常被认为是禁止的条件下仍保持支撑。基于文献的稀有报道，我们表明基于衍生自（C 5 Me 5）Ru或（C 5 H 5）Ru部分的反应中间体的一系列有机金属转化是与空气相容的。
• Diazadiene stabilized palladacyclopent 2 enes and the catalytic addition of various allylic systems to dimethyl acetylenedicarboxylate
  作者：Christian Munz、Constantin Stephen、Heindirk tom Dieck

  DOI：10.1016/0022-328x(91)86318-k

  日期：1991.4

  With diazadiene (dad=Rn=Cr'-Cr=NR)as co-ligand the palladacyclopent-2-enes 3 formed by direct coupling of a 1-alkene and an acetylenedicarboxylic acid esters can be trapped. With activated 1-alkanes such as allylic alcohols the reaction becomes catalytic, yeilding linear addition-products4-11 from two molecules of the alkene and one molecule of the alkyne; no simple reductive elimination occurs, but

  以二氮杂二烯（dad ＝ Rn ＝ Cr′-Cr ＝ NR）作为共配体，可以捕获通过1-烯烃与乙炔二羧酸酯的直接偶联而形成的五环金属环戊烯-2-烯3。在活化的1-烷烃（如烯丙醇）的作用下，该反应变为催化，由两个分子的烯烃和一个分子的炔烃生成线性加成产物4-11。没有简单的还原消除发生，而是消除了一摩尔水。烯丙基酯类似地反应，但是主要的产物是环状的1：2-加成产物15（也由离去基团的损失形成）。离去基团的消除可能是反应的驱动力，因为仅观察到使消除成为可能的β-H-转移。
• Palladium-Catalyzed Benzannulation from Alkynes and Allylic Compounds
  作者：Naofumi Tsukada、Shuichi Sugawara、Keiichiro Nakaoka、Yoshio Inoue

  DOI：10.1021/jo026857r

  日期：2003.7.1

  Various alkynes reacted with allyl tosylates in the presence of palladium catalysts, giving polysubstituted benzenes with good to high regioselectivity. Pentasubstituted and trisubstituted benzenes were readily prepared by reaction of internal alkynes and terminal alkynes, respectively. The combination of allyl alcohols and p-toluenesulfonic anhydride could be utilized in place of isolated allyl tosylates. The cyclization of diynes with allyl tosylate afforded bicyclic compounds containing an aromatic ring.
• JP2001019662A
  申请人：——

  公开号：JP2001019662A

  公开（公告）日：2001-01-23
• ALKYL BENZENE TETRACARBOXYLIC DIANHYDRIDE, MANUFACTURING METHOD THEREOF, POLYIMIDE, AND APPLICATION THEREOF
  申请人：Suzuki Hideo

  公开号：US20110257361A1

  公开（公告）日：2011-10-20

  Disclosed is a 5-alkyl-1,2,3,4-benzene tetracarboxylic-1:2,3:4-dianhydride which is represented by the general formula (1) and has excellent solubility with respect to various organic solvents. Depending on the diamine that is used, a polyimide with excellent heat resistance or a polyimide with good workability at a low melting point can be provided, and in addition, a polyimide that exhibits excellent characteristics for electronic materials or the like can be provided. (In the formula, R 1 represents an alkyl group with carbon number 1-10.)