1-(4-叔丁基-2-羟基苯基)乙酮 | 113027-08-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(4-叔丁基-2-羟基苯基)乙酮
• 英文名称: 4-t-butyl-2-hydroxyphenyl methyl ketone
• 英文别名: 2-hydroxy-4-t-butylphenyl methyl ketone；1-(4-tert-butyl-2-hydroxyphenyl)ethanone；4'-tert-butyl-2'-hydroxyacetophenone；1-(4-tert-Butyl-2-hydroxyphenyl)ethan-1-one
• CAS: 113027-08-0
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: OAUPGHMBSLFFGE-UHFFFAOYSA-N

物化性质

• 沸点：
  293.0±28.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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-(4-叔丁基-2-羟基苯基)乙酮 在 吡啶 、 氢氧化钾 、 硫酸 作用下， 以 溶剂黄146 为溶剂， 生成 4-(7-tert-Butyl-4-oxo-4H-chromen-2-yl)-benzoic acid methyl ester
  参考文献：
  名称：

  Retinobenzoic acids. 2. Structure-activity relationships of chalcone-4-carboxylic acids and flavone-4'-carboxylic acids

  摘要：

  The structure-activity relationships of (E)-chalcone-4-carboxylic acids, which are retinoidal benzoic acids represented by R-Ph-X-Ph-COOH (4, X = -COCH = CH-), are discussed on the basis of differentiation-inducing activity on human promyelocytic leukemia cells HL-60. The activity was increased by the substitution of a bulky alkyl group(s) (R), and among such compounds, (E)-4-[3-(3,5-di-tert-butylphenyl)-3-oxo-1-propenyl]benzoic acid (Ch55) and (E)-4-[3-oxo-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1 -propenyl]benzoic acid (Ch80) are several times more active than retinoic acid. Though the stable conformer of chalcone derivatives is linear (s-cis form), the conformationally restricted analogue 4-(6,7,8,9-tetrahydro-6,6,9,9-tetramethyl-4H-4-oxonaphtho[2,3-b]py ran-2-yl)benzoic acid (Fv80) is more active than Ch80. While the effect of introduction of an oxygen atom varied, 4-[1-hydroxy-3-oxo-3-(5,6,7,8-tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2 - naphthalenyl)-1-propenyl]benzoic acid (Re80), regarded as a derivative of Ch80 with two additional hydroxyl groups, has very strong activity.

  DOI：

  10.1021/jm00124a016
• 作为产物：
  描述：

  1-(4-(tert-butyl)-2-hydroxyphenyl)ethan-1-one oxime 在 水 、 sodium hydrogensulfite 作用下， 以 乙醇 为溶剂， 反应 13.0h， 以91%的产率得到1-(4-叔丁基-2-羟基苯基)乙酮
  参考文献：
  名称：

  O-Acetyl Oximes as Transformable Directing Groups for Pd-Catalyzed C−H Bond Functionalization

  摘要：

  O-Acetyl oximes serve as effective directing groups for Pd-catalyzed sp(2) and sp(3) C-H functionalization reactions. The C-H functionalization products can be subsequently transformed into ortho- or beta-functionalized ketones, alcohols, amines, and heterocycles.

  DOI：

  10.1021/ol902720d

文献信息

• Titanium(IV) Chloride-Mediated Ortho-Acylation of Phenols and Naphthols
  作者：Nurulain T. Zaveri、Ahlem Bensari

  DOI：10.1055/s-2003-36822

  日期：——

  The use of titanium(IV) chloride as a Lewis acid for direct ortho-acylation of phenols and naphthols proves to be a convenient, more general and direct route to various hydroxyaryl ketones. The route is regioselective, leading to ortho C-acylated products in satisfactory to high yields in most cases.

  使用四氯化钛作为路易斯酸，进行酚和萘酚的直接邻位酰基化反应，被证明是一种方便、更普遍且直接的途径，可用于制备各种羟基芳基酮。该路线具有区域选择性，在大多数情况下能够产生令人满意的至高产率的邻位C-酰基化产物。
• Synthesis of polybenzoquinazolines via an intramolecular dehydration of photocyclization
  作者：Wei Wei、Chenchen Li、Tao Wang、Dian Liu、Zunting Zhang

  DOI：10.1016/j.tet.2016.04.080

  日期：2016.8

  intramolecular dehydration of photocyclization. The intermediates were obtained by the condensation of 3-arylchromone with formamidine, acetamidine or guanidine refluxing in ethanol, respectively. Irradiation of the corresponding intermediates by a high-pressure mercury lamp in 19:1 (v/v) EtOHH2O or 18:1:1 (v/v) EtOHH2O-Dioxane lead to target products. This photocyclization showed advantages including

  苯并[ ħ ] -naphth [1,2 ˚F ]喹唑啉和苯并[ ħ ] -phenanthren [9,10- ˚F ] quinazoines从中间体合成4-（2-羟基苯基）-5-（萘-1-基）嘧啶和4-（2-羟基苯基）-5-（菲基-1-基）嘧啶通过分子内脱水作用而光环化。通过使3-芳基色酮与甲am，乙am或胍在乙醇中回流分别缩合获得中间体。高压汞灯以19：1（v / v）EtOH H 2 O或18：1：1（v / v）EtOH H 2辐照相应的中间体邻二恶烷导致目标产品。该光环化显示出包括无催化剂和温和的反应条件的优点。此外，水是该反应的唯一副产物。测定了2-氨基-12-甲氧基-苯并[ h ]-萘并[1,2- f ]喹唑啉的晶体结构，并研究了这些聚苯并喹唑啉的荧光性质。
• Flavone carboxylic acid derivatives
  申请人：Shionogi & Co., Ltd.

  公开号：US04831052A1

  公开（公告）日：1989-05-16

  Novel flavone carboxylic acid derivatives, intermediates therefor, and method for the preparation thereof, and their use in the differentiation of certain types of malignant cells, are all disclosed, certain of the novel compounds disclosed to be superior to retinoic acid in their activity.

  小说黄酮羧酸衍生物，其中间体及其制备方法，以及它们在区分某些类型的恶性细胞中的应用，均已披露，其中某些新化合物在活性上被证实优于视黄酸。
• Antagonists of the Vanilloid Receptor Subtype 1 (VR1) and Uses Thereof
  申请人：Brown S. Brian

  公开号：US20070249614A1

  公开（公告）日：2007-10-25

  The present invention is directed to compounds of formula (I) wherein variables X 1 , X 2 , Y, R 1a , R 1b , R 2a , R 2b , A 1 , A 2 , A 3 , and A 4 are as defined in the description, and methods of use to treat pain, neuropathic pain, allodynia, pain associated with inflammation or an inflammatory disease, inflammatory hyperalgesia, bladder overactivity, and urinary incontinence.

  本发明涉及式(I)的化合物，其中变量X1、X2、Y、R1a、R1b、R2a、R2b、A1、A2、A3和A4如描述中定义，以及用于治疗疼痛、神经痛、触痛、与炎症或炎症性疾病相关的疼痛、炎症性过敏反应、膀胱过度活跃和尿失禁的使用方法。
• Catalytic direct C-acylation of phenol and naphthol derivatives using carboxylic acids as acylating reagents
  作者：Shū Kobayashi、Mitsuhiro Moriwaki、Iwao Hachiya

  DOI：10.1016/0040-4039(96)00790-3

  日期：1996.6

  Direct regioselective C-acylation of phenol and naphthol derivatives was carried out by using carboxylic acids as acylating reagents. The reactions proceeded smoothly in the presence of a catalytic amount of Hf(OTf)4 to afford the corresponding aromatic ketones in good yields.

  苯酚和萘酚衍生物的直接区域选择性C-酰化是通过使用羧酸作为酰化剂进行的。在催化量的Hf（OTf）4存在下，反应平稳进行，以高收率得到相应的芳族酮。