2-hydroxy-4-(3-methylbut-2-enyloxy)benzaldehyde | 61235-37-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-4-(3-methylbut-2-enyloxy)benzaldehyde
• 英文别名: 2-Hydroxy-4-(O-prenyl)benzaldehyde；2-hydroxy-4-prenyloxybenzaldehyde；4-((3-methyl)but-2-enyloxy)-2-hydroxybenzaldehyde；2hydroxy-4-(3methylbut-2-enyloxy)benzaldehyde；2-Hydroxy-4-(3methylbut-2-enyloxy)benzaldehyde；2-hydroxy-4-(3-methylbut-2-enoxy)benzaldehyde
• CAS: 61235-37-8
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: PXNOVNOMHKRGFX-UHFFFAOYSA-N

物化性质

• 沸点：
  338.9±27.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-4-(3-methylbut-2-enyloxy)benzaldehyde 在 氢氧化钾 、 sodium hydroxide 、 potassium carbonate 、 2,3-二甲基苯胺 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 79.02h， 生成 甘草查耳酮A
  参考文献：
  名称：

  Islam, Azizul; Hossain, M Amzad, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 7, p. 713 - 715

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-diprenyloxybenzaldehyde 在 四氯化钛 、 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 以90%的产率得到2-hydroxy-4-(3-methylbut-2-enyloxy)benzaldehyde
  参考文献：
  名称：

  TiCl 4 - n -Bu 4 NI混合试剂对异戊二烯醚的高选择性裂解

  摘要：

  水杨酸盐的用的TiCl异戊二烯基醚的治疗4 - ñ -Bu 4 NI混合试剂导致CO键的裂解，以提供水杨酸乙酯以定量产率。另一方面，当使用对-异戊烯氧基苯甲酸乙酯作为底物时，没有观察到裂解反应。在该系统中，证明了醚的裂解反应通过底物中相邻基团的螯合作用而加速。

  DOI：

  10.1016/s0040-4039(99)01717-7

文献信息

• Treatment and prophylaxis of diseases caused by parasites, or bacteria
  申请人：Statens Seruminstitut

  公开号：US05985935A1

  公开（公告）日：1999-11-16

  Aromatic compounds, or prodrugs thereof, which contain an alkylating site and which are capable of alkylating the thiol group in N-acetyl-L-cysteine, in particular bis-aromatic .alpha.,.beta.-unsaturated ketones, are used for the preparation of pharmaceutical compositions or medicated feed, food or drinking water for the treatment or prophylaxis of diseases caused by microorganisms or parasites, in particular protozoa such as Leishmannia, Trypanosoma, Toxoplasma, Plasmodium, Pneumocystis, Babesia and Theileria, intestinal protozoa such as Trichormionas and Ciardia; Coccidia such as Eimeria, Isospora, Cryptosporidium; Cappilaria, Microsporidium, Sarcocystis. Trichlodina, Trichoditella, Dacihylogurus, Pseudodacthylogurus, Acantocephalus, Ichthylophtherius, Botrecephalus; and intracellular bacteria, in particular Mycobacterium, Legionella species, Listeria and Salmonella. Preferred compounds have the formula (II): X.sub.m --Ph--C(O)--CH.dbd.CH--Ph--Y.sub.n, wherein each phenyl group (Ph) may be mono- or polysubstituted; X and Y designate AR.sub.H or AZ, wherein A is O, S, NH or N(C.sub.1-6 alkyl), R.sub.H designates aliphatic hydrocarbyl, and Z is H or a masking group which is decomposed to liberate AH; m is 0, 1 or 2, and n is 0, 1, 2 or 3, whereby, when m is 2, then the two X are the same or different, and when n is 2 or 3, then the two or three Y are the same or different, with the proviso that n and m are not both 0. As examples of such compounds, chalcones, e.g. licochalcone A (obtainable i.a. from batches of Chinese licorice root of Glycyrrhiza species, e.g. G. uralensis or G. inflata) as well as hydroxy, alk(en)yl, and/or alk(en)yloxy analogues thereof are active in vitro and/or in vivo against i.a. L. major and P. falciparum.

  含有烷基化位点的芳香化合物或其前药，能够烷基化N-乙酰-L-半胱氨酸中的硫醇基团，特别是双芳基α，β-不饱和酮，用于制备用于治疗或预防由微生物或寄生虫引起的疾病的药物组合物或药物饲料、食品或饮用水，特别是原虫，如利什曼原虫、锥虫、弓形虫、疟原虫、肺孢子虫、巴贝斯虫和泰勒原虫，肠道原虫，如毛滴虫和贾第虫；球虫，如艾美利亚球虫、异孢子球虫、隐孢子虫；毛细管虫、微小孢子虫、肉囊虫、三鞭毛虫、三鞭毛虫、卵泡头虫、假卵泡头虫、棘头虫、鱼皮虫、蠕虫头虫；以及细胞内细菌，特别是分枝杆菌、军团菌属、李斯特菌和沙门氏菌。优选化合物具有以下公式（II）：X.sub.m --Ph--C(O)--CH.dbd.CH--Ph--Y.sub.n，其中每个苯基（Ph）可以是单取代或多取代；X和Y代表AR.sub.H或AZ，其中A为O、S、NH或N（C.sub.1-6烷基），R.sub.H代表脂肪烃基，Z为H或分解以释放AH的掩蔽基；m为0、1或2，n为0、1、2或3，当m为2时，两个X相同或不同，当n为2或3时，两个或三个Y相同或不同，但n和m不能同时为0。作为这类化合物的例子，香豆素，例如甘草属植物（例如华北甘草或气球甘草）根的批次中可获得的甘草香豆素A，以及其羟基、烯烃基和/或烯烃氧基类似物在体外和/或体内对利什曼原虫和疟原虫具有活性。
• Condensation of salicylaldehydes with ethyl 4,4,4-trichloro-3-oxobutanoate: a facile approach for the synthesis of substituted 2H-chromene-3-carboxylates
  作者：Mudulkar Sairam、Gannerla Saidachary、Bhimapaka China Raju

  DOI：10.1016/j.tetlet.2015.01.114

  日期：2015.3

  A highly efficient and simple protocol has been developed for the preparation of ethyl 2-oxo-2H-chromene-3-carboxylates 3a–v by the condensation of salicylaldehydes 1a–v with ethyl 4,4,4-trichloro-3-oxobutanoate 2 for the first time. The reaction is proceeding via Knoevenagel pathway followed by a selective addition of the phenolic hydroxyl group to the carbonyl group adjacent to the CCl3 group rather

  通过将水杨醛1a - v与4,4,4-三氯-3-氧代丁酸乙酯缩合，已开发出一种高效且简单的方案，用于制备2-oxo-2 H-色烯-3-羧酸乙酯3a – v第一次2。该反应通过Knoevenagel途径进行，随后由于强的电子吸收作用，将酚羟基选择性地添加到与CCl 3基团相邻的羰基上而不是酯羰基上，并且生成了香豆素衍生物3a，消除了CHCl 3。
• Facile Synthesis of Substituted Ethyl 2-(Chloromethyl)-2-hydroxy-2H-1-benzopyran-3-carboxylates
  作者：Bhimapaka China Raju、Gannerla Saidachary、Jaladi Ashok Kumar、Balasubramanian Sridhar

  DOI：10.1002/hlca.201000181

  日期：2011.2

  Ethyl 2‐(chloromethyl)‐2‐hydroxy‐2H‐chromene‐3‐carboxylates 2a–2j have been synthesized by reaction of substituted salicylaldehydes with ethyl 4‐chloro‐3‐oxobutanoate, in the presence of piperidine in CH2Cl2 at room temperature, in good yields.

  在有哌啶的CH 2 Cl 2存在下，取代的水杨醛与4-氯-3-氧代丁酸乙酯反应，合成了2-（氯甲基）-2-羟基-2 H-亚铬基-3-羧酸乙酯2a – 2j。在室温下，收率良好。
• Bis-aromatic a,&bgr;-unsaturated ketones
  申请人：Lica Pharmaceuticals A/S

  公开号：US06603046B1

  公开（公告）日：2003-08-05

  The invention is drawn to novel bis-aromatic a,&bgr;-unsaturated ketones. The compounds are useful in the treatment and prophylaxis of diseases caused by parasites or bacteria.

  本发明涉及新型的双芳基α,β-不饱和酮。该化合物在治疗和预防由寄生虫或细菌引起的疾病方面是有用的。
• Synthesis and biological evaluation of allylated and prenylated mono-carbonyl analogs of curcumin as anti-inflammatory agents
  作者：Zhiguo Liu、Longguang Tang、Peng Zou、Yali Zhang、Zhe Wang、Qilu Fang、Lili Jiang、Gaozhi Chen、Zheng Xu、Huajie Zhang、Guang Liang

  DOI：10.1016/j.ejmech.2013.10.061

  日期：2014.3

  Curcumin has been shown to possess anti-inflammatory activities but has been limited for its low stability and poor bioavailability. We have previously reported four series of 5-carbon linker-containing mono-carbonyl analogs of curcumin (MACs). In continuation of our ongoing research, we designed and synthesized 33 novel allylated or prenylated MACs here, and evaluated their anti-inflammatory effects in RAW 264.7 macrophages. A majority of them effectively inhibited the LPS-induced expression of TNF-alpha and IL-6, especially IL-6. The preliminary SAR and quantitative SAR analysis were conducted. Compound 14q is the most potent analog among them, and exhibits significant protection against LPS-induced death in septic mice. Together, these data present a series of new analogs of curcumin as promising anti-inflammatory agents. (C) 2013 Elsevier Masson SAS. All rights reserved.