(E)-1-(4-(allyloxy)phenyl)-3-phenylprop-2-en-1-one | 868612-22-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(4-(allyloxy)phenyl)-3-phenylprop-2-en-1-one
• 英文别名: (E)-1-(4-Allyloxy-phenyl)-3-phenyl-propenone；(E)-3-phenyl-1-(4-prop-2-enoxyphenyl)prop-2-en-1-one
• CAS: 868612-22-0
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: JHNKJAZRIYZLGV-MDWZMJQESA-N

物化性质

• 沸点：
  428.8±45.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-(allyloxy)phenyl)-3-phenylprop-2-en-1-one 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以48 %的产率得到(3-phenyloxiran-2-yl)-(4-prop-2-enoxyphenyl)methanone
  参考文献：
  名称：

  室温下锰催化化学选择性直接氢化 α,β-环氧酮和 α-酮酰胺

  摘要：

  使用 2.0 bar H 2和钳式连接的 Mn(I) 催化剂在室温 (25 °C) 下实现 α,β-环氧酮和 α-酮酰胺的化学选择性氢化，从而提供具有合成价值的 α-羟基环氧化物和 α-羟基酰胺。该方案适用于各种烷基和芳基取代的 α,β-环氧酮，包括萜烯（α-紫罗兰酮、nootkatone 和 R-香芹酮）和类固醇（睾酮和黄体酮）衍生的环氧酮，并且耐受 H 2敏感官能团，如卤化物、乙酰基、腈基、硝基、环氧基、烯基和炔基。此外，带有可还原官能团（包括乙酰基和重氮苯）的α-酮酰胺在此方案下未受影响，并选择性地转化为α-羟基酰胺。初步的机理研究强调了金属-配体协同H 2活化过程。

  DOI：

  10.1002/adsc.202400267
• 作为产物：
  描述：

  在 1-methyl-3-pentyl-1H-imidazolium tetrafluoroborate 作用下， 反应 0.05h， 以72%的产率得到(E)-1-(4-(allyloxy)phenyl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  Catalysis by Ionic Liquid. A Green Protocol for the Stereoselective Debromination of vicinal-Dibromides by [pmIm]BF₄ under Microwave Irradiation

  摘要：

  [GRAPHIC]An easily accessible ionic liquid, 1-methyl-3-pentylimidazolium fluoroborate, [pmIm]BF4, has been demonstrated to be an efficient catalyst as well as reaction medium for the stereoselective debromination of a variety of structurally diverse vicinal-dibromides to the corresponding (E)-alkenes in high yields under microwave irradiation. This reaction does not require any organic solvent and any metal or any conventional reducing agent, and the ionic liquid is recycled without any appreciable loss of its catalytic efficiency.

  DOI：

  10.1021/jo051373r

文献信息

• A New and Direct Synthesis of Chalcones Via TFAA-H3PO4 Mediated C-C Bond Forming Reaction
  作者：Kavitha Kankanala、Lingam Venkata Reddy、Vangala Ranga Reddy、Khagga Mukkanti、Sarbani Pal

  DOI：10.2174/157017811794557750

  日期：2011.1.1

  A number of α,β-unsaturated carboxylic acids were reacted with electron rich arenes or heteroarene in the presence of trifluoroacetic anhydride (TFAA) and H3PO4 at room temperature to give a variety of chalcone derivatives in good to excellent yields. The methodology was used to prepare novel compounds of potential pharmacological significances.

  多种α,β-不饱和羧酸与富电子的芳烃或杂芳烃在三氟乙酸酐（TFAA）和磷酸（H3PO4）存在下，于室温反应，以良好至优秀的产率合成了多种查耳酮衍生物。该方法学被用于制备具有潜在药理学意义的创新化合物。
• A Simple, Efficient, and Green Procedure for the 1,4-Addition of Thiols to Conjugated Alkenes and Alkynes Catalyzed by Sodium Acetate in Aqueous Medium
  作者：Brindaban C. Ranu、Tanmay Mandal

  DOI：10.1071/ch06455

  日期：——

  A benign and inexpensive salt, sodium acetate, efficiently catalyzes 1,4-addition of thiols to a variety of conjugated alkenes such as α,β-unsaturated ketones, aldehydes, carboxylic esters, nitriles, nitro compounds, and chalcones in aqueous THF. The reactions are clean, fast, and high yielding.

  一种温和且廉价的盐乙酸钠可在 THF 水溶液中有效催化硫醇与各种共轭烯烃（例如 α,β-不饱和酮、醛、羧酸酯、腈、硝基化合物和查耳酮）的 1,4-加成反应。反应干净、快速且产率高。
• Catalytic Asymmetric Cyclopropanation of Enones with Dimethyloxosulfonium Methylide Promoted by a La−Li₃−(Biphenyldiolate)₃ + NaI Complex
  作者：Hiroyuki Kakei、Toshihiko Sone、Yoshihiro Sohtome、Shigeki Matsunaga、Masakatsu Shibasaki

  DOI：10.1021/ja076797c

  日期：2007.11.1

  Catalytic asymmetric cyclopropanation of enones with dimethyloxosulfonium methylide using a La−Li3−(biphenyldiolate)3 + NaI complex is described. The present method is complementary to the previously reported catalytic enantioselective methods in terms of ylides used, and trans products were exclusively obtained in good yield (96−73%) and high enantioselectivity (99−84% ee). Use of biphenyldiol 1b-H2

  描述了使用 La−Li3−(biphenyldiolate)3 + NaI 复合物对烯酮与二甲基氧锍甲基化物的催化不对称环丙烷化反应。本方法在使用的叶立德方面是对先前报道的催化对映选择性方法的补充，并且反式产物仅以良好的产率 (96-73%) 和高对映选择性 (99-84% ee) 获得。联苯二醇 1b-H2 和 NaI 添加剂的使用对于实现高对映选择性至关重要。
• Biologically active 1,3-bis-aromatic-prop-2-en-1-ones, 1,3-bis-aromatic-propan-1-ones, and 1,3-bis-aromatic-prop-2-yn-1-ones
  申请人：Statens Serum Institute

  公开号：US20030065039A1

  公开（公告）日：2003-04-03

  The invention relates to the use of 1,3-bis-aromatic-prop-2-en-1-ones (chalcones), 1,3-bis-aromatic-propan-1-ones (dihydrochalcones), and 1,3-bis-aromatic-prop-2-yn-1-ones for the preparation of pharmaceutical compositions for the treatment or prophylaxis of a number of serious diseases including i) conditions relating to harmful effects of inflammatory cytokines, ii) conditions involving infection by Helicobacter species, iii) conditions involving infection by viruses, iv) neoplastic disorders, and v) conditions caused by microorganisms or parasites. The invention also relates to novel chalcones and dihydrochalcones (especially alkoxy substituted variants) having advantageous substitution patterns with respect to their effect as drug substances, and to methods of preparing them, as well as to pharmaceutical compositions comprising the novel chalcones. Moreover, the present invention relates to a method for the isolation of Leishmania fumarate reductase, QSAR methodologies for selecting potent compounds for the above-mentioned purposes.

  该发明涉及使用1,3-双芳基-丙-2-烯-1-酮（香豆素）、1,3-双芳基-丙酮-1-酮（二氢香豆素）和1,3-双芳基-丙-2-炔-1-酮制备用于治疗或预防多种严重疾病的药物组合物，包括i）与炎症细胞因子有害作用相关的疾病，ii）涉及幽门螺旋杆菌感染的疾病，iii）涉及病毒感染的疾病，iv）肿瘤性疾病，v）由微生物或寄生虫引起的疾病。该发明还涉及新型香豆素和二氢香豆素（特别是烷氧基取代变体），其具有有利的取代模式，对其作为药物物质的效果，以及制备它们的方法，以及包含新型香豆素的药物组合物。此外，本发明涉及一种用于分离利什曼氏弓形虫富马酸还原酶的方法，以及用于选择上述目的的有效化合物的QSAR方法。
• [EN] TREATMENT AND PROPHYLAXIS OF DISEASES CAUSED BY PARASITES OR BACTERIA<br/>[FR] TRAITEMENT ET PROPHYLAXIE D'AFFECTIONS PARASITAIRES OU BACTERIENNES
  申请人：——

  公开号：WO1995006628A1

  公开（公告）日：1995-03-09

  [EN] 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 Leishmania, Trypanosoma, Toxoplasma, Plasmodium, Pneumocystis, Babesia and Theileria, intestinal protozoa such as Trichomonas and Ciardia; Coccidia such as Eimeria, Isospora, Cryptosporidium; Capillaria, Microsporidium, Sarcocystis, Trichodina, Trichodinella, Dacthylogurus, Pseudodacthylogurus, Acantocephalus, Ichthylophtherius, Botrecephalus; and intracellular bacteria, in particular Mycobacterium, Legionella species, Listeria and Salmonella. Preferred compounds have the formula (II): Xm-Ph-C(O)-CH=CH-Ph-Yn, wherein each phenyl group (Ph) may be mono- or polysubstituted; X and Y designate ARH or AZ, wherein A is O, S, NH or N(C1-6 alkyl), RH 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.
  [FR] Composés aromatiques ou leurs précurseurs contenant un site d'alkylation et capables d'alkyler le groupe thiol de la N-acétyl-L-cystéine, et en particuler les cétones bi-aromatiques alpha , beta -insaturées, et servant à préparer des compositions pharmaceutiques ou des aliments, nutriments ou boissons médicalisés servant au traitement ou à la prophylaxie de maladies causées par des micro-organismes ou parasites, et en particulier par des protozoaires tels que les Leishmania, Trypanosoma, Toxoplasma, Plasmodium, Pneumocystis, Babesia, Theileria et des protozoaires intestinaux tels que les Trichomonas et Ciardia; des coccidies telles que les Eimeria, Isospora, Cryptosporidum, Cappilaria, Microsporidium, Sarcocystis, Trichodina, Trichodinella, Dacthylogurus, Pseudodacthylogurus, Acantocephalus, Ichthylophtherius, Botrecephalus; et des bactéries intracellulaires en particulier les Mycobacterium, les espèces legionella, les Listeria et les Salmonella. Les composés préférés présentent la formule (II): Xm-Ph-C(O)-CH=CH-Ph-Yn où chacun des groupes phényl (Ph) peut être mono ou polysubstitué, X et Y désignent ARH ou AZ, où A est O, S, NH ou N(C1-6alkyl), RH représente un hydrocarbyle aliphatique, Z est H ou un groupe masque qui se décompose en libérant AH, m est 0, 1 ou 2, et n est 0, 1, 2 ou 3, où si m est 2, les deux X sont identiques ou différents et où si n est 2 ou 3, les deux ou trois Y sont identiques ou différents, pour autant que m et n ne soient pas tous deux nuls. On peut citer comme exemples de ces composés des chalcones et notamment la licochalcone A (tirée notamment de racines du réglisse chinois de l'espèce Glycyrrhiza, p.ex. du G. uralensis ou du G. inflata), ainsi que leurs analogues hydroxy, alc(én)yle et/ou alc(én)yloxy qui agissent in vitro et/ou in vivo notamment contre le L. major et le P. falciparum.