1-(3,5-di-tert-butyl-4-hydroxyphenyl)pentan-1-one | 14035-37-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3,5-di-tert-butyl-4-hydroxyphenyl)pentan-1-one
• 英文别名: 4-(4'-pentynoyl)-2,6-di-tert-butylphenol；3,5-di(t-butyl)-4-hydroxyvalerophenone；1-[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1-pentanone；1-(3,5-ditert-butyl-4-hydroxyphenyl)pentan-1-one
• CAS: 14035-37-1
• 化学式: C₁₉H₃₀O₂
• 分子量: 290.446
• InChiKey: KSYGEVRKMFJMCE-UHFFFAOYSA-N

物化性质

• 熔点：
  75-78 °C
• 沸点：
  357.0±37.0 °C(Predicted)
• 密度：
  0.960±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3,5-di-tert-butyl-4-hydroxyphenyl)pentan-1-one 在 四氯化钛 、 三乙胺 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 26.5h， 生成 (E)-2-(3,5-di-tert-butyl-4-acetoxyphenyl)-1-(4-methylsulfonylphenyl)-1-phenylhex-1-ene
  参考文献：
  名称：

  Synthesis and biological evaluation of acyclic triaryl (Z)-olefins possessing a 3,5-di-tert-butyl-4-hydroxyphenyl pharmacophore: Dual inhibitors of cyclooxygenases and lipoxygenases

  摘要：

  A new class of regioisomeric acyclic triaryl (Z)-olefins possessing a 3,5-di-tert-butyl-4-hydroxyphenyl (DTBHP) 5-lipoxygenase (5-LOX) pharmacophore that is vicinal to a para-methanesulfonylphenyl cyclooxygenase-2 (COX-2) pharmacophore were designed for evaluation as selective COX-2 and/or 5-LOX inhibitors. The target compounds were synthesized via a highly stereoselective McMurry olefination cross-coupling reaction. This key synthetic step afforded a (Z):(E) olefinic mixture with a predominance for the (Z)-olefin stereoisomer. Structure-activity studies for the (Z)-1-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-(4-methanesulfonylphenyl)-1-phenylalk-1-ene regioisomers showed that COX-1 inhibition decreased, COX-2 inhibition increased, and the COX-2 selectivity index (SI) increased as the chain length of the alkyl substituent attached to the olefinic double bond was increased (Et -> n-butyl -> n-heptyl). In this group of compounds, inhibition of both 5-LOX and 15-LOX was dependent upon the length of the alkyl substituent with the hex-1-ene compound 9c having a n-butyl substituent exhibiting potent inhibition of both 5-LOX (IC50 = 0.3 mu M) and 15-LOX (IC50 = 0.8 mu M) relative to the inactive (IC50 > 10 mu M) Et and n-heptyl analogs. Compound 9c is of particular interest since it also exhibits a dual inhibitory activity against the COX (COX-1 IC50 = 3.0 mu M, and COX-2 IC50 = 0.36 mu M, COX-2 SI = 8.3) isozymes. A comparison of the relative inhibitory activities of the two groups of regioisomers investigated shows that the regioisomers in which the alkyl substituent is attached to the same olefinic carbon atom (C-2) as the para-methanesulfonylphenyl moiety generally exhibit a greater potency with respect to COX-2 inhibition. The 4-hydroxy substituent in the 3,5-di-tert-butyl-4-hydroxyphenyl moiety is essential for COX and LOX inhibition since 3,5-di-tert-butyl-4-acetoxyphenyl derivatives were inactive inhibitors. These structure-activity data indicate acyclic triaryl (Z)-olefins constitute a suitable template for the design of dual COX-2/LOX inhibitors. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.054
• 作为产物：
  描述：

  2,6-二叔丁基苯酚 生成 1-(3,5-di-tert-butyl-4-hydroxyphenyl)pentan-1-one
  参考文献：
  名称：

  Process for the preparation of 2-alkyl-4-acyl-6-tert-butylphenol

  摘要：

  本发明涉及一种制备具有以下化学结构的2-烷基-4-酰基-6-叔丁基苯酚化合物的方法：##STR1## 其中-R是选择自--C.tbd.CH和--CH.dbd.C.dbd.CH.sub.2的末端不饱和基团的脂肪基，而R'则选择自1到约10个碳原子的饱和、直链、支链或环状烷基；该2-烷基-4-酰基-6-叔丁基苯酚化合物在反应混合物中产生，该反应混合物包括相应的2-烷基-6-叔丁基苯酚：##STR2## 相应的羧酸：RCOOH和三氟乙酸酐。

  公开号：

  US05126487A1

文献信息

• Iodide as an Activating Agent for Acid Chlorides in Acylation Reactions
  作者：Russell J. Wakeham、James E. Taylor、Steven D. Bull、James A. Morris、Jonathan M. J. Williams

  DOI：10.1021/ol400035f

  日期：2013.2.1

  Acid chlorides can be activated using a simple iodide source to undergo nucleophilic attack from a variety of relatively weak nucleophiles. These include Friedel–Crafts acylation of N-methylpyrroles, N-acylation of sulfonamides, and acylation reactions of hindered phenol derivatives. The reaction is believed to proceed through a transient acid iodide intermediate.

  可以使用简单的碘源活化酰氯，使其受到各种相对较弱的亲核试剂的亲核攻击。其中包括N-甲基吡咯的Friedel-Crafts酰化，磺酰胺的N-酰化以及受阻酚衍生物的酰化反应。据信该反应通过过渡性碘酸中间体进行。
• Monastyrskaya; Lyutkin; Gorbunov, Russian Journal of Organic Chemistry, 1997, vol. 33, # 10, p. 1409 - 1416
  作者：Monastyrskaya、Lyutkin、Gorbunov、Klimov

  DOI：——

  日期：——
• US4130666A
  申请人：——

  公开号：US4130666A

  公开（公告）日：1978-12-19