2-acetoxy-3,5-di-tert-butylbenzaldehyde | 173030-55-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2-acetoxy-3,5-di-tert-butylbenzaldehyde
• 英文别名: 3,5-di-tert-butylacetylsalicylic aldehyde；4,6-di-tert-butyl-2-formylphenyl acetate；4,6-Di-t-butyl-2-formylphenyl acetate；(2,4-ditert-butyl-6-formylphenyl) acetate
• CAS: 173030-55-2
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: KHULDTDJJJRKSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-acetoxy-3,5-di-tert-butylbenzaldehyde 在 sodium acetate 作用下， 反应 2.5h， 以97%的产率得到3,5-二叔丁基水杨酸
  参考文献：
  名称：

  Urotropin synthesis of 3,5-di-tert-butylsalicylic acid derivatives

  摘要：

  The stability of 3,5-di-tert-butylsalicylic aldehyde against oxidation is due to autoinhibiting of the chain process. However its oxidation into 3,5-di-tert-butylsalicylic acid was performed at the use of acetyl protection of the hydroxy group. In reaction of 6-bromo-2,4-di-tert-butylphenol with urotropin the formation was discovered of 3,5-di-tert-butylsalicylic acid, its nitrile and amide.

  DOI：

  10.1134/s1070428007100132
• 作为产物：
  描述：

  Acetic acid 2,4-di-tert-butyl-6-[1,3]dithian-2-yl-phenyl ester 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.0h， 以99%的产率得到2-acetoxy-3,5-di-tert-butylbenzaldehyde
  参考文献：
  名称：

  温和的化学选择方案，用于去除由Dess-Martin高碘烷介导的硫代缩酮和硫缩醛。

  摘要：

  [反应：见正文]本文介绍了使用Dess-Martin高碘烷（DMP）试剂去除硫缩醛和硫缩酮的有用方法的开发。与现有方法相比，该协议具有一般的反应性，与各种官能团的相容性以及方便的反应时间。还讨论了化学选择性实验，涉及的功能可能会被DMP氧化，底物对水解速率的定性影响以及硫代乙缩醛向乙缩醛的直接转化。

  DOI：

  10.1021/ol027518n

文献信息

• Discovery of a potent phenolic N1-benzylidene–pyridinecarboxamidrazone selective against Gram-positive bacteria
  作者：Daniel L. Rathbone、Katy J. Parker、Michael D. Coleman、Peter A. Lambert、David C. Billington

  DOI：10.1016/j.bmcl.2005.11.005

  日期：2006.2

  As part of a study into antimycobacterial compounds a set of phenolic N-1-benzylidene-pyridinecarboxamidrazones was prepared and evaluated. This report describes the unexpected discovery of a potent compound with a pronounced selectivity for Gram-positive bacteria over Gram-negative micro-organisms. In addition, this compound is active against various drug-resistant Gram-positive bacteria. (c) 2005 Elsevier Ltd. All rights reserved.
• Anionic condensations of 3,5-di-tert-butyl-4(2)-hydroxybenzaldehydes in the presence of weak bases
  作者：V. B. Vol’eva、I. S. Belostotskaya、N. L. Komissarova、L. N. Kurkovskaya

  DOI：10.1134/s1070428008060043

  日期：2008.6

  Products of the reactions of 4- and 2-hydroxy-3,5-di-tert-butyl-benzaldehydes with malonic acid, diethyl malonate, and acetic anhydride in the presence of weak bases were isolated and identified. The reactions of 3,5-di-tert-butyl-4-hydroxybenzaldehyde with malonic acid and acetic anhydride in the presence of sodium acetate and piperidine gave 3,5-di-tert-butyl-4-hydroxycinnamic acid. The reaction of its 2-hydroxy isomer with acetic anhydride stopped at the stage of formation of the corresponding O-acetyl derivative, while in the reaction with malonic acid the corresponding substituted cinnamic acid and its lactone (coumarin derivative) were formed as intermediate products in a transformation sequence finally leading to 3-(3,5-di-tertbutyl-2-hydroxyphenyl)-3-piperidinopropionic acid and 6,8-di-tert-butyl-2-oxo-3,4-dihydro-2H-chromen-4-ylacetic acid. Analogous differences were typical of reactions of isomeric 4- and 2-hydroxy-3,5-di-tert-butylbenzaldehydes with diethyl malonate. The transformations of the 2-hydroxy isomer were accompanied by hydrolysis and formation of an adduct of intermediate coumarin derivative with diethyl malonate and piperidine.
• Synthesis and structure of anhydrodimers of salicylaldehydes
  作者：V. B. Vol'eva、I. S. Belostotskaya、O. V. Shishkin、Yu. T. Struchkov、V. V. Ershov

  DOI：10.1007/bf00714437

  日期：1995.8

  Anhydrodimers have been synthesized by reactions of salicylaldehyde and 3,5-di-tert-butylsalicylaldehyde with SOCl2 or PCI5. A mechanism of condensation has been proposed, and the molecular structure of dibenzo-2,6,9-trioxabicyclo[3.3.1]nona-3,7-diene has been determined by X-ray structural analysis.
• A Mild, Chemoselective Protocol for the Removal of Thioketals and Thioacetals Mediated by Dess−Martin Periodinane
  作者：Neil F. Langille、Les A. Dakin、James S. Panek

  DOI：10.1021/ol027518n

  日期：2003.2.1

  development of a useful procedure for the removal of thioacetals and thioketals using Dess-Martin periodinane (DMP) reagent. In contrast to existing methods, this protocol offers general reactivity, compatibility with a wide range of functional groups, and convenient reaction times. Also discussed are chemoselectivity experiments involving functionalities that may be subject to oxidation by DMP, qualitative

  [反应：见正文]本文介绍了使用Dess-Martin高碘烷（DMP）试剂去除硫缩醛和硫缩酮的有用方法的开发。与现有方法相比，该协议具有一般的反应性，与各种官能团的相容性以及方便的反应时间。还讨论了化学选择性实验，涉及的功能可能会被DMP氧化，底物对水解速率的定性影响以及硫代乙缩醛向乙缩醛的直接转化。
• Urotropin synthesis of 3,5-di-tert-butylsalicylic acid derivatives
  作者：V. B. Vol’eva、I. S. Belostotskaya、N. L. Komissarova、L. N. Kurkovskaya、A. P. Pleshakova、T. I. Prokofeva

  DOI：10.1134/s1070428007100132

  日期：2007.10

  The stability of 3,5-di-tert-butylsalicylic aldehyde against oxidation is due to autoinhibiting of the chain process. However its oxidation into 3,5-di-tert-butylsalicylic acid was performed at the use of acetyl protection of the hydroxy group. In reaction of 6-bromo-2,4-di-tert-butylphenol with urotropin the formation was discovered of 3,5-di-tert-butylsalicylic acid, its nitrile and amide.