3-(4-溴苯基)-2-甲基丙-2-烯醛 | 23632-41-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 中文名称: 3-(4-溴苯基)-2-甲基丙-2-烯醛
• 英文名称: 3-(4-bromophenyl)-2-methacrolein
• 英文别名: (E)-3-(4-Bromo-phenyl)-2-methyl-propenal；3-(4-Bromophenyl)-2-methylprop-2-enal；3-(4-bromophenyl)-2-methylprop-2-enal
• CAS: 23632-41-9
• 化学式: C₁₀H₉BrO
• 分子量: 225.085
• InChiKey: RNBCQLCYZIHPON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-(4-(trifluoromethyl)phenyl)dihydro-2H-pyran-2,4(3H)-dione 、 3-(4-溴苯基)-2-甲基丙-2-烯醛 在 乙二胺-N,N’-二乙酸 、 氧气 、 rose bengal 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 2-(4-bromophenyl)-3-methyl-7-(4-(trifluoromethyl)phenyl)-7,8-dihydro-2H-3,8a-epidioxypyrano[4,3-b]pyran-5(3H)-one
  参考文献：
  名称：

  Design, synthesis, and in vitro cancer cell growth inhibition evaluation and antimalarial testing of trioxanes installed in cyclic 2-enoate substructures

  摘要：

  A novel series of 1,2,4-trioxanes were synthesized from 2H-pyrans via photooxidation, and their antiproliferative and growth factor inhibitory activity has been investigated across a variety of human cancer cell lines. Compounds 5k, 51, 5s, 7a and 7c exhibited the highest activity and selectivity against a human leukemia (MV4-11) cell line (IC50 = 0.5 mu M). Compound 5o showed the highest growth factor inhibitory activity against a melanoma (LOX-IMVI) cancer cell line (GI(50) = 1.0 mu M). A SAR study has confirmed the importance of the 1,2,4-trioxane unit as a pharmacophore for anticancer activity. The computer-assisted database analysis, COMPARE, has suggested that the compounds have unique mechanisms of actions that were different from those of known anticancer drugs. Some of the selected trioxanes were tested against the NF54 strain, albeit showing weak antiplasmodial activity. The molecular docking of trioxanes and hemin reveals that a short distance (130 angstrom) leads to their physical contact. The UV-vis spectroscopic analysis ensured the definite complexation between 1,2,4-trioxanes and hemin. The role of hemin-trioxane interaction in the hemin-induced oxidative damage has been studied using methylene blue as a substrate by UV-vis spectroscopy. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.008
• 作为产物：
  描述：

  丙醛 、 对溴苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 3-(4-溴苯基)-2-甲基丙-2-烯醛
  参考文献：
  名称：

  Ungesättigte Oxime, 28. Mitt. Notiz zur Darstellung α-verzweigter Zimtaldehyde und ihrer Oxime. The Synthesis of α-branched Cinnamyl Aldehydes and of their Oximes

  摘要：

  DOI：

  10.1002/ardp.19863190719

文献信息

• Annulation of 2<i>H</i>-Pyran onto 1-Oxa- or 1-Azacyclohexane-2,4-diones and Their Analogues via Sequential Condensation with α-Substituted Enals and 6π-Electrocyclization
  作者：Md. Imran Hossain、Elkhabiry Shaban、Taku Ikemi、Wei Peng、Hiroyuki Kawafuchi、Tsutomu Inokuchi

  DOI：10.1246/bcsj.20130069

  日期：2013.7.15

  2H-Pyrans are constructed on a 1-oxa- or 1-azacyclohexane-2,4-dione core via Knoevenagel condensation with enals followed by 6π-electrocyclization, which are readily catalyzed with ethylenediammonium diacetate. This formal [3 + 3] strategy constitutes C–O and C–C bond making and the diastereomer formation is circumvented using 6,6-disubstitution with the same aryl group in the 1-oxacyclohexane-2,4-diones. This facile methodology significantly advances the access to polysubstituted bicyclic 2H-pyrans with a versatile substrate choice and improved stability of the product.

  通过Knoevenagel缩合反应与烯醛反应，随后进行6π-电环化反应，以1-氧杂-或1-氮杂环己烷-2,4-二酮为核心构建了2H-吡喃衍生物，这些反应易于用乙二胺二乙酸盐催化。这种形式上的[3 + 3]策略构成了C–O和C–C键的形成，并通过在1-氧杂环己烷-2,4-二酮中使用相同的芳基进行6,6-二取代来避免立体异构体的形成。这种简便的方法学极大地促进了多取代双环2H-吡喃的合成，具有多样化的底物选择和产品稳定性的提高。
• Enantioselective 1,2-Addition of α-Aminoalkyl Radical to Aldehydes via Visible-Light Photoredox Initiated Chiral Oxazaborolidinium Ion Catalysis
  作者：Jae Yeon Kim、Yea Suel Lee、Yuna Choi、Do Hyun Ryu

  DOI：10.1021/acscatal.0c02443

  日期：2020.9.18

  Enantioselective 1,2-addition reaction of α-aminoalkyl radical to α,β-unsaturated or aromatic aldehydes to synthesize highly optically active β-amino alcohols has been developed. In the presence of chiral oxazaborolidinium ion catalyst and photosensitizer, the reaction provides desired β-amino allylic or benzylic alcohols with high yields (up to 99%) and high enantioselectivities (up to 98% ee).

  已经开发了α-氨基烷基与α，β-不饱和或芳族醛的对映选择性1，2-加成反应，以合成高度旋光活性的β-氨基醇。在手性恶唑硼烷鎓离子催化剂和光敏剂的存在下，反应以高产率（高达99％）和高对映选择性（高达98％ee）提供所需的β-氨基烯丙基或苄基醇。
• Trio Catalysis Merging Enamine, Brønsted Acid, and Metal Lewis Acid Catalysis: Asymmetric Three-Component Aza-Diels-Alder Reaction of Substituted Cinnamaldehydes, Cyclic Ketones, and Arylamines
  作者：Yongming Deng、Siddhartha Kumar、Kraig Wheeler、Hong Wang

  DOI：10.1002/chem.201406569

  日期：2015.5.18

  phosphoric acid, and Y(OTf)3, enables the combination of enamine catalysis with both hard metal Lewis acid catalysis and Brønsted acid catalysis for the first time. Using this catalyst system, a three‐component aza‐Diels–Alder reaction of substituted cinnamaldehyde, cyclic ketone, and arylamine is carried out with high chemo‐ and enantioselectivity, affording a series of optically active 1,4‐dihydropyridine

  由芳基胺，BINOL衍生的磷酸和Y（OTf）3组成的三重催化剂体系，首次使烯胺催化与硬质金属路易斯酸催化和布朗斯台德酸催化结合起来。使用这种催化剂体系，可以以高化学和对映选择性进行取代的肉桂醛，环酮和芳胺的三组分氮杂-狄尔斯-阿尔德反应，得到一系列光学活性的1,4-二氢吡啶（DHP）衍生物。以91–99％  ee和59–84％的产率获得。还获得了具有良好对映选择性和中等产率的带有手性季碳中心的DHP（三个实例）。还进行了初步的机械研究。
• 7位-氢取代吡唑并[1,5-a]嘧啶类化合物的制备方法
  申请人：安徽中医药大学

  公开号：CN117777142A

  公开（公告）日：2024-03-29

  本发明公开了一种7位‑氢取代吡唑并[1,5‑a]嘧啶类化合物的制备方法。所述制备方法包括：将式(I)所示化合物与式(II)或式(III)之一所示化合物、硫氰酸盐、含碘氧化剂和溶剂接触使反应。本发明制备方法具有操作简便、原料价廉易得、底物适用范围广、收率高等特点，所得产物是重要的医药中间体；#imgabs0#
• CN115974707
  申请人：——

  公开号：——

  公开（公告）日：——