4-Methyl-orthobenzoesaeure-triethylester | 59118-32-0

• 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: 4-Methyl-orthobenzoesaeure-triethylester
• 英文别名: 1-methyl-4-triethoxymethyl-benzene；1-Methyl-4-(triethoxymethyl)benzene
• CAS: 59118-32-0
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: VHLYZEQCFWYRBO-UHFFFAOYSA-N

物化性质

• 沸点：
  132-134 °C(Press: 12 Torr)
• 密度：
  0.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Methyl-orthobenzoesaeure-triethylester 、 2-amino-N'-phenylbenzohydrazide 在 silver(I) acetate 、 palladium diacetate 、 溶剂黄146 作用下， 反应 48.0h， 以85%的产率得到3-methyl-5-phenylindazol[3,2-b]quinazolin-7 (5H)-one
  参考文献：
  名称：

  Palladium-Catalyzed Cascade Reaction of 2-Amino-N′-arylbenzohydrazides with Triethyl Orthobenzoates To Construct Indazolo[3,2-b]quinazolinones

  摘要：

  A palladium-catalyzed sequential cyclization/C-H activation cascade reaction of 2-amino-N'-arylbenzohydrazides with triethyl orthobenzoates has been developed, providing indazolo[3,2-b]quinazolinones in good to high yields. Two key intermediates of the reaction, 2-phenyl-3-(phenylamino)quinazolinone and C-H insertion palladacycle, were isolated, and their structures were unambiguously confirmed by X-ray crystallography. This method represents an unprecedented example of a halogen-free protocol to access indazolo[3,2-b]quinazolinones. Moreover, this chemistry also provides a useful tool for the discovery of fluorescent materials.

  DOI：

  10.1021/jo5024848
• 作为产物：
  描述：

  锡烷,二丁基二乙氧基- 、 4-methyl-dithiobenzoic acid methyl ester 生成 4-Methyl-orthobenzoesaeure-triethylester
  参考文献：
  名称：

  A NOVEL METHOD OF PREPARATION FOR ORTHOCARBOXYLATES FROM DITHIOCARBOXYLATES AND DIALKOXYDIBUTYLSTANNANES

  摘要：

  二硫代羧酸甲酯与二烷氧基二丁基锡烷在 60-95°C 的温度下反应，可以得到相应的三烷基原羧酸酯，收率很高。

  DOI：

  10.1246/cl.1976.891

文献信息

• Novel multicomponent synthesis of pyrido[2,3-<i>b</i>]indoles
  作者：Saman Damavandi、Reza Sandaroos

  DOI：10.1515/hc.2011.036

  日期：2011.12.1

  Abstract A series of pyrido[2,3-b]indole derivatives was synthesized via a novel multicomponent reaction catalyzed by ferric hydrogen sulfate.

  摘要 通过硫酸氢铁催化的新型多组分反应合成了一系列吡啶并[2,3-b]吲哚衍生物。
• Novel multicomponent synthesis of 2,9-dihydro-9-methyl-2-oxo-4-aryl-1H-pyrido[2,3-b]indole-3-carbonitrile compounds
  作者：SAMAN DAMAVANDI、REZA SANDAROOS

  DOI：10.1007/s12039-013-0369-y

  日期：2013.1

  Novel multicomponent approach for the synthesis of 2,9-dihydro-2-oxo-4-aryl-1H-pyrido[2,3-b]indole-3-carbonitrile derivatives via one-pot cyclocondensation reaction of substituted (triethoxymethyl)arene, 1-methyl-1H-indol-2-ol and cyanoacetamide in the presence of silica supported ionic liquid [pmim]HSO4 SiO2 (silica-supported 1-methyl-3-(triethoxysilylpropyl)imidazolium hydrogensulphate) has been reported.

  通过取代(三乙氧基甲基)炔的一锅环缩合反应合成 2,9-二氢-2-氧代-4-芳基-1H-吡啶并[2,3-b]吲哚-3-甲腈衍生物的新型多组分方法、1-甲基-1H-吲哚-2-醇和氰乙酰胺在二氧化硅支撑离子液体 [pmim]HSO4 SiO2（二氧化硅支撑的 1-甲基-3-(三乙氧基硅丙基)咪唑鎓硫酸氢盐）存在下发生的单锅环缩合反应，制备出 1-甲基-4-芳基-1H-吡啶并[2,3-b]吲哚-3-甲腈衍生物。
• Polymeric catalyst for the synthesis of new pyrido[2,3-b]indoles
  作者：Gholam Hossein Zohuri、Saman Damavandi、Reza Sandaroos

  DOI：10.1007/s11164-012-0743-2

  日期：2013.5

  for the one-pot synthesis of novel 2,9-dihydro-2-oxo-4-aryl-1H-pyrido[2,3-b]indole-3-carbonitrile derivatives by condensation of substituted (triethoxymethyl)arene, 1-methyl-1H-indol-2-ol and cyanoacetamide in the presence of a catalytic amount of crosslinked poly(2-acrylamido-2-methyl propane sulfonic acid) (AMPS) as an efficient and heterogeneous catalyst. This polymeric solid acid catalyst is stable

  通过缩合缩合反应一锅法合成新的2,9-二氢-2-氧-4-芳基1 H-吡啶并[2,3 - b ]吲哚-3-腈衍生物。催化量的交联聚（2-丙烯酰胺基-2-甲基丙烷磺酸）（AMPS）的存在下，取代的（三乙氧基甲基）芳烃，1-甲基-1 H-吲哚-2-醇和氰基乙酰胺是一种高效且多相的催化剂。该聚合固体酸催化剂是稳定的，并且可以容易地回收和再利用而其活性没有明显变化。
• Bennett,G.B. et al., Journal of Heterocyclic Chemistry, 1979, vol. 16, p. 1389 - 1392
  作者：Bennett,G.B. et al.

  DOI：——

  日期：——
• Novel Functionalized Pyridoindole Derivatives Catalyzed by Iron(III) Triflate
  作者：Saman Damavandi、Reza Sandaroos

  DOI：10.1080/15533174.2015.1031009

  日期：2015.11.2

  A variety of novel 1H-pyrido[2,3-b]indole-3-carbonitrile derivatives have been synthesized via solvent-free one-pot cyclocondensation of substituted (triethoxymethyl)arene, 1-methyl-1H-indol-2-ol, and cyanoacetamide catalyzed by iron(III) triflate.