ethyl-2-formyl-4-methylbenzoate

• 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: ethyl-2-formyl-4-methylbenzoate
• 英文别名: Ethyl 2-formyl-4-methylbenzoate
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: CTHFCXAUMLFWGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-(bromomethyl)-1,3-dihydroisobenzofuran-1-one 在 palladium on activated charcoal calcium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 水 、 氢气 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 54.0h， 生成 ethyl-2-formyl-4-methylbenzoate
  参考文献：
  名称：

  Aromatische Spirane, 21. Mitt: Darstellung von Methylphthalaldehyds�uren und ihren Ethylund Methylestern als Synthone f�r Synthesen von methylierten 2,2?-Spirobiindandionen

  摘要：

  The isomeric methyl phthalaldehydic acids 11 were obtained from phthalides 4 by bromation (NBS) to the 3-bromo derivatives 7 and subsequent hydrolysis with water. 4 in turn were accessible from dimethyl methyl benzoates 1 by dibromination with NBS and subsequent thermical cyclization to the bromo derivatives 3 which, on catalytic dehalogenation, afforded the phthalides 4. Reaction of 11 with methanol or ethanol gave the pseudo-esters 13 and 14, resp. Short treatment of 11 with diazomethane on the other hand yielded the methyl formyl benzoates 15b to 15e. Prolonged reaction (several hours) gave the oxiranyl compounds 17; in addition, the acetonyl derivatives 18 were also found, obviously formed by a double methylene insertion into 15. All reactions proceeded with good to excellent yields.

  DOI：

  10.1007/bf00807401

文献信息

• β-Chloro-α,β-unsaturated carbonyls as convenient precursors of highly substituted benzenes
  作者：T. M. Barhoumi-Slimi、M. Ourévitch

  DOI：10.1007/s13738-017-1263-1

  日期：2018.3

  β-chloro-α,β-unsaturated carbonyl compounds 1–3 with different dienes were carried out to afford highly functionalized cyclohexenes 4–9, bearing quaternary centers, in good yields. These cycloadducts (CAs) undergo dehydrochlorination with subsequent aromatization in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene DBU to produce new substituted benzenes 11–14. Compound 10 is the product of lactonization

  的三个狄尔斯-阿尔德反应β氯代α，β不饱和羰基化合物1-3与不同的二烯进行了纯化，得到高度官能化环己烯4-9，轴承季中心，以良好产率。这些环加合物（CAs）在1,8-二氮杂双环[5.4.0]十一碳-7-烯DBU存在下进行脱氯化氢反应，随后进行芳构化，以生成新的取代苯11-14。化合物10是内酯化和从化合物7中除去HCl分子的产物。所有产品均通过NMR，IR，元素分析和部分质谱（MS）表征。异构体的结构分配是根据NMR化学位移和偶联常数，使用1D，2D和heteronee NMR技术进行的。
• Aromatische Spirane, 21. Mitt: Darstellung von Methylphthalaldehyds�uren und ihren Ethylund Methylestern als Synthone f�r Synthesen von methylierten 2,2?-Spirobiindandionen
  作者：H. K. Neudeck

  DOI：10.1007/bf00807401

  日期：1996.2

  The isomeric methyl phthalaldehydic acids 11 were obtained from phthalides 4 by bromation (NBS) to the 3-bromo derivatives 7 and subsequent hydrolysis with water. 4 in turn were accessible from dimethyl methyl benzoates 1 by dibromination with NBS and subsequent thermical cyclization to the bromo derivatives 3 which, on catalytic dehalogenation, afforded the phthalides 4. Reaction of 11 with methanol or ethanol gave the pseudo-esters 13 and 14, resp. Short treatment of 11 with diazomethane on the other hand yielded the methyl formyl benzoates 15b to 15e. Prolonged reaction (several hours) gave the oxiranyl compounds 17; in addition, the acetonyl derivatives 18 were also found, obviously formed by a double methylene insertion into 15. All reactions proceeded with good to excellent yields.