Ph3P=CHC(O)C6H3-2,5-(OMe)2 | 141957-50-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ph3P=CHC(O)C6H3-2,5-(OMe)2
• 英文别名: 1-(2,5-Dimethoxyphenyl)-2-(triphenyl-lambda~5~-phosphanylidene)ethan-1-one；1-(2,5-dimethoxyphenyl)-2-(triphenyl-λ5-phosphanylidene)ethanone
• CAS: 141957-50-8
• 化学式: C₂₈H₂₅O₃P
• 分子量: 440.478
• InChiKey: PEHATOZGMNIENO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ph3P=CHC(O)C6H3-2,5-(OMe)2 在 铁粉 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 0.5h， 生成 (E)-1-(2,5-dimethoxyphenyl)-3-(2-isothiocyanatophenyl)prop-2-en-1-one
  参考文献：
  名称：

  1,3-苯并噻嗪衍生物的对映选择性合成：一种有机催化化学选择性方法

  摘要：

  在此，首次建立了硫醇与 2-异硫氰基查耳酮的高度化学选择性 1,2-加成，然后是对映选择性分子内硫-迈克尔加成级联，以构建对映体富集的 [1,3]-苯并噻嗪衍生物。金鸡纳衍生的 squaramide 催化剂提供了良好的产品收率和对映选择性，具有广泛的底物适应性。此外，该策略已扩展到二苯基氧化膦亲核试剂，以获得富含对映体的有机磷取代的 [1,3]-苯并噻嗪。放大反应和合成转化证明了该协议的可行性。

  DOI：

  10.1021/acs.orglett.3c01120
• 作为产物：
  描述：

  2,5-二甲氧基苯甲酸 、 Bis(trimethylsilyl)methylidene triphenylphosphorane 以 四氢呋喃 为溶剂， 以65%的产率得到Ph3P=CHC(O)C6H3-2,5-(OMe)2
  参考文献：
  名称：

  Bestmann, Hans Juergen; Dostalek, Roman; Bauroth, Bernd, Angewandte Chemie, 1992, vol. 104, # 8, p. 1062 - 1064

  摘要：

  DOI：

文献信息

• One-pot Wittig olefination–Suzuki reaction—the compatibility of conjugated phosphoranes in Pd(0) catalysed C–C-bond forming reactions
  作者：Thies Thiemann、Masataka Watanabe、Yasuko Tanaka、Shuntaro Mataka

  DOI：10.1039/b516724h

  日期：——

  acids can be subjected to a combined Suzuki coupling–Wittig olefination in their reaction with arene halides and conjugated phosphoranes. Also, the transformations can be carried out under ultrasonication in a biphasic medium of aq. Na2CO3 and hexane–ether, where phosphonium salts are used as the starting materials.

  甲酰芳基硼酸和甲酰戊烯基硼酸在与芳烃的反应中可以进行合并的Suzuki偶联-Wittig烯化反应 卤化物 和共轭 磷烷。同样，可以在以下条件下进行转换超音波在双相水溶液中。Na 2 CO 3和正己烷–醚，其中phospho盐用作起始原料。
• Synthesis and biological evaluation of some undecanone derivatives
  作者：Bharani Meka、Suryachandra Rao Ravada、Harikrishna Kancharla、Trimurtulu Golakoti

  DOI：10.1007/s00044-017-2006-7

  日期：2017.12

  The total synthesis of Ardisinone E [15, 1-(2,4,6-trihydroxy phenyl)-11-(2-hydroxyphenyl)-undecan-1-one], a natural diarylundecanone, isolated from Ardisia arborescens, was accomplished along with 16 new diarylundecanone analogs (18a–p), by modified Wittig reaction. The structures of the compounds were confirmed by 1H, 13C and mass spectral data. Compound 15 showed potent cytotoxic activity with an

  Ardisinone E [总合成15 1-（2,4,6-三羟基-苯基）-11-（2-羟基苯基）-undecan -1-酮]，天然diarylundecanone，分离自朱砂藜，用沿完成通过改良的Wittig反应，得到16种新的二芳基十一烷酮类似物（18a – p）。化合物的结构由1 H，13 C和质谱数据证实。在盐水虾致死率测定模型中，化合物15显示出强的细胞毒性，ED 50为4.19 µg / mL。化合物18c，18e，18j，18k，18l和在NBT自由基测定中，18m具有很强的抗氧化活性，IC 50值分别为18.75、12.28、18.35、11.04、12.05和11.32 µg / mL。化合物18e，18k和18m还显示出显着的5-脂氧合酶抑制潜力，IC 50值分别为12.8、15.23和15.23 µg / mL。
• Synthesis, in vitro and in silico evaluation of diaryl heptanones as potential 5LOX enzyme inhibitors
  作者：Bharani Meka、Suryachandra Rao Ravada、Murali Krishna Kumar Muthyala、Purna Nagasree Kurre、Trimurtulu Golakoti

  DOI：10.1016/j.bioorg.2018.06.015

  日期：2018.10

  synthesized and their structures were confirmed by its 1H, 13C NMR and Mass spectral data. These analogs were evaluated for their anti-oxidant activity and potential to inhibit 5-lipoxygenase. Compounds 12k and 12o showed potent in vitro 5-lipoxygenase enzyme inhibitory activity with IC50 values of 22.2, 21.5 μM, which are comparable to curcumin (24.4 μM). Further they also have shown significant antioxidant

  合成了一系列新的二芳基庚烷（12a-q），并通过其1 H，13 C NMR和质谱数据证实了它们的结构。对这些类似物的抗氧化活性和抑制5-脂氧合酶的潜力进行了评估。化合物12k和12o显示出有效的体外5-脂氧合酶抑制活性，IC 50值为22.2，21.5μM，与姜黄素（24.4μM）相当。此外，它们还显示出显着的抗氧化剂活性。分子对接研究清楚地表明了这些化合物的结合能和效能之间的相关性。
• Divergent Behavior in the Cyclopalladation of Phosphorus Ylides and Iminophosphoranes
  作者：David Aguilar、Miguel Angel Aragüés、Raquel Bielsa、Elena Serrano、Rafael Navarro、Esteban P. Urriolabeitia

  DOI：10.1021/om7002877

  日期：2007.7.1

  The cyclopalladation of the stabilized iminophosphoranes Ph3PNC(O)C6H4R (R = H 1a, 4-OMe 1b, 3-OMe 1c, 2-Me 1d, 3-Me 1e) results in the regioselective activation of the ortho CH bond of the benzamide ring, giving exo-[Pd(mu-Cl)C,N-C6H3(R)C(O)NPPh3-2}}](2) (R = H 2a, 5-OMe 2b, 4-OMe 2c, 3-Me 2d, 4-Me 2e). The palladated ligand behaves as a strong C,N-chelating group and cannot be easily displaced by other chelating ligands. This is clear from the reaction of 2c with Tl(acac), py, or AgClO4/LandL, which gives [Pd(acac)C,N-C6H3(MeO-4)C(O)NPPh3-2}}] (3c), [PdClC,N-C6H3(MeO-4)C(O)NPPh3-2}}(py)] (4c), or [PdC,N-C6H3(MeO-4)C(O)NPPh3-2}}(LandL)]ClO4 (LandL = dppe 5c, bipy 6c, phen 7c). However, Pd(OAc)(2) reacts with the ylides Ph3PCHC(O)C6H4R (R = H 8a, 3-OMe 8b, 2,5-(OMe)(2) 8c) to give the C,C-orthometalated complexes [Pd(mu-Cl)C,C-[C6H4(PPh2CHC(O)C6H4R)-2]}] (R = H 9a, 3-OMe 9b, 2,5-(OMe)(2) 9c), which are also regioselectively obtained. The C,C-metalated chelate is very stable, as shown by the reactions of 9b with Tl(acac), PPh3, and AgClO4/LandL. The X-ray structures of 2d and 9b have been determined. Unexpectedly, the reaction of Pd(OAc)(2) with the ylide [Ph3PCHC(O)C6H3-2,4-(OMe)(2)] (16) gives the polymer [(mu-Cl)PdC6H4(PPh2CH-C(O)C6H2-3,5-(OMe)(2))-2}-kappa-C,C,C,O)Pd(mu-Cl)](n) (17) as a result of a double palladation, giving two types of metalacycles: in one of them, the Pd atom is bonded to the ylidic C alpha atom and has activated an ortho C(Ph)-H bond of the PPh3 group; in the other one, the Pd atom is bonded to the carbonyl oxygen and has activated an ortho C-H bond of the C6H3(OMe)(2) unit. This tetradentate ylide ligand is remarkably stable.