phenyl dichloroacetate | 10565-20-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: phenyl dichloroacetate
• 英文别名: Phenyl-dichloracetat；phenyl 2,2-dichloroacetate
• CAS: 10565-20-5
• 化学式: C₈H₆Cl₂O₂
• 分子量: 205.04
• InChiKey: FALZSEYHTLDSIT-UHFFFAOYSA-N

物化性质

• 熔点：
  48 °C
• 沸点：
  247.5 °C
• 密度：
  1.2991 g/cm3(Temp: 50 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  phenyl dichloroacetate 在 氯 作用下， 生成 dichloro-acetic acid-(1,2,3,4,5,6-hexachloro-cyclohexyl ester)
  参考文献：
  名称：

  The Addition-Chlorination of Phenol¹

  摘要：

  DOI：

  10.1021/jo01092a034
• 作为产物：
  描述：

  (E)-1,2-dichloro-1-ethoxy-ethene 在 氯 作用下， 生成 phenyl dichloroacetate
  参考文献：
  名称：

  Crompton; Triffit, Journal of the Chemical Society, 1921, vol. 119, p. 1875

  摘要：

  DOI：

文献信息

• Platinum on Carbon-Catalyzed Precise Reduction Control of Trichloromethyl to Geminal-Dichloromethyl Groups
  作者：Takahiro Imanishi、Yuta Fujiwara、Yoshinari Sawama、Yasunari Monguchi、Hironao Sajiki

  DOI：10.1002/adsc.201100778

  日期：2012.3.16

  Geminal‐dichloromethyl derivatives could be efficiently synthesized by the highly chemoselective platinum on carbon‐catalyzed mono‐dechlorination of trichloromethyl substrates in dimethylacetamide (DMA) as a specific solvent at 25 °C under a hydrogen atmosphere.

  在25°C的氢气氛围中，通过在二甲基乙酰胺（DMA）中作为特定溶剂，对三氯甲基底物进行碳催化的三氯甲基底物进行碳催化的单脱氯反应，可以高效地合成具有高化学选择性的铂，从而有效地合成Geminal-dichloromethyl衍生物。
• Dichloroacetophenones targeting at pyruvate dehydrogenase kinase 1 with improved selectivity and antiproliferative activity: Synthesis and structure-activity relationships
  作者：Shao-Lin Zhang、Zheng Yang、Xiaohui Hu、Kin Yip Tam

  DOI：10.1016/j.bmcl.2018.09.026

  日期：2018.11

  Dichloroacetophenone is a pyruvate dehydrogenase kinase 1 (PDK1) inhibitor with suboptimal kinase selectivity. Herein, we report the synthesis and biological evaluation of a series of novel dichloroacetophenones. Structure-activity relationship analyses (SARs) enabled us to identify three potent compounds, namely 54, 55, and 64, which inhibited PDK1 function, activated pyruvate dehydrogenase complex

  二氯苯乙酮是一种丙酮酸脱氢酶激酶1（PDK1）抑制剂，具有次优的激酶选择性。在这里，我们报告了一系列新型二氯苯乙酮的合成和生物学评估。结构-活性关系分析（SARS）使我们能够确定3个有效的化合物，即54，55，和64，其抑制PDK1功能，激活丙酮酸脱氢酶复合物，和降低的NCI-H1975细胞的增殖。线粒体生物能量学吸附测定法表明，54，55，和64增强的癌细胞中氧化磷酸化，这可能有助于所观察到的抗增殖作用。总的来说，这些结果表明：54，55，和64可以是有前途的化合物为有效的PDK1抑制剂的开发。
• Variation in Bone Biomechanical Properties, Microstructure, and Density in BXH Recombinant Inbred Mice
  作者：Charles H. Turner、Yeou-Fang Hsieh、Ralph Müller、Mary L. Bouxsein、Clifford J. Rosen、Margaret E. McCrann、Leah Rae Donahue、Wesley G. Beamer

  DOI：10.1359/jbmr.2001.16.2.206

  日期：——

  To test the hypothesis that factors associated with bone strength (i.e., volumetric bone mineral density [vBMD], geometry, and microstructure) have heritable components, we exploited the 12 BXH recombinant inbred (RI) strains of mice derived from C57BL/6J (B6; low bone mass) and C3H/HeJ (C3H; high bone mass) progenitor strains. The femurs and lumbar vertebrae from each BXH RI strain were characterized for phenotypes of vBMD, microstructural, biomechanical, and geometrical properties. Methods included bending (femur) and compression (vertebra) testing, peripheral quantitative computed tomography (pQCT), and microcomputed tomography (μCT). Segregation patterns of femoral and vertebral biomechanical properties among the BXH RI strains suggested polygenic regulation. Femoral biomechanical properties were strongly associated with femoral width in the anteroposterior (AP) direction and cortical thickness‐geometric properties with complex genetic regulation. Vertebral vBMD and biomechanical properties measured in BXH RI strains showed a greater variability than either B6 or C3H progenitors, suggesting both progenitor strains have independent subsets of genes that yield similar vBMD and strength. The μCT and pQCT data suggested that the distribution of vertebral mineral into cortical and trabecular compartments is regulated genetically. Although the B6 and C3H progenitors had similar vertebral strength, their vertebral structures were markedly different: B6 had good trabecular bone structure and modest cortical bone mineral content (BMC), whereas C3H had high cortical BMC combined with a deficiency in trabecular structure. These structural traits segregated independently in the BXH RI strains. Finally, vertebral strength was not correlated consistently with femoral strength among the BXH RI strains, suggesting genetic regulation of bone strength is site specific.

  为了检验与骨骼强度相关的因素（即体积骨矿物质密度[vBMD]、几何形状和微观结构）是否具有可遗传的成分，我们利用了从C57BL/6J（B6；低骨质量）和C3H/HeJ（C3H；高骨质量）亲本品系衍生出的12种BXH重组近交（RI）小鼠品系。对每个BXH RI品系的小鼠股骨和腰椎进行了vBMD、微观结构、生物力学和几何特性的表型特征描述。方法包括弯曲（股骨）和压缩（椎骨）测试、外周定量计算机断层扫描（pQCT）和微型计算机断层扫描（μCT）。股骨和椎骨的生物力学特性在BXH RI品系间的分离模式表明其受多基因调控。股骨的生物力学特性与前后方向（AP）的股骨宽度以及皮质厚度-几何特性强烈相关，这些特性受复杂的遗传调控。BXH RI品系中测量的椎骨vBMD和生物力学特性的变异性比B6或C3H亲本品系更大，表明这两个亲本品系都有独立的一部分基因会产生相似的vBMD和强度。μCT和pQCT数据显示椎骨矿物质在皮质和松质骨隔室中的分布受遗传调控。尽管B6和C3H亲本品系具有相似的椎骨强度，但它们的椎骨结构明显不同：B6具有良好的松质骨结构和适度的皮质骨矿物含量（BMC），而C3H具有高皮质BMC但松质骨结构存在缺陷。这些结构特性在BXH RI品系中独立分离。最后，BXH RI品系中椎骨强度与股骨强度的相关性不一致，表明骨骼强度的遗传调控具有部位特异性。
• Design, synthesis, molecular docking, biological evaluations and QSAR studies of novel dichloroacetate analogues as anticancer agent
  作者：Masood Fereidoonnezhad、S. Mohammad Hossein Tabaei、Amirhossein Sakhteman、Hassan Seradj、Zeinab Faghih、Zahra Faghih、Ayyub Mojaddami、Batool Sadeghian、Zahra Rezaei

  DOI：10.1016/j.molstruc.2020.128689

  日期：2020.12

  its proliferation. In this study, a series of novel N-aryl-2,2-dichloroacetamide and aryl-2,2-dichloroacetate derivatives were designed and synthesized. Their cytotoxic activities against various human cancer cell lines including A549, HCA-7, MCF-7, MDA-MB-231, KB and SKOV3 were evaluated. These compounds showed satisfactory potencies with much higher anticancer activity than the parent compound DCA

  摘要 二氯乙酸 (DCA) 作为线粒体靶向小分子，通过抑制丙酮酸脱氢酶激酶 (PDK1-4)，促进线粒体调节的细胞凋亡，从而抑制肿瘤生长并减少其增殖。在本研究中，设计并合成了一系列新型 N-芳基-2,2-二氯乙酰胺和芳基-2,2-二氯乙酸衍生物。评估了它们对各种人类癌细胞系（包括 A549、HCA-7、MCF-7、MDA-MB-231、KB 和 SKOV3）的细胞毒活性。与母体化合物 DCA 相比，这些化合物显示出令人满意的抗癌活性，对研究的癌细胞系具有更高的抗癌活性。还进行了分子对接研究以发现它们的结合位点以及它们与 PDK 同工酶的相互作用类型。在合成的化合物中，2,2-二氯-N-(9,10-dioxo-9, 10-dihydroanthracen-1-yl)acetamide (f1) 也可以诱导 A549 细胞凋亡。因此，化合物 f1 可能具有进一步研究药物开发的潜在价值。还使用一系列化学计量学方法探索了此类化合物的
• Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses
  作者：Fengying Liang、Kazuo Eda、Takashi Okazoe、Akihiro Wada、Nobuaki Mori、Katsuhiko Konishi、Akihiko Tsuda

  DOI：10.1021/acs.joc.1c00334

  日期：2021.5.7

  The Vilsmeier reagent (VR), first reported a century ago, is a versatile reagent in a variety of organic reactions. It is used extensively in formylation reactions. However, the synthesis of VR generally requires highly toxic and corrosive reagents such as POCl3, SOCl2, or COCl2. In this study, we found that VR is readily obtained from a CHCl3 solution containing N,N-dimethylformamide or N,N-dimethylacetamide

  Vilsmeier试剂（VR）于一个世纪前首次报道，是一种用于多种有机反应的多功能试剂。它被广泛用于甲酰化反应中。然而，VR的合成通常需要剧毒和腐蚀性试剂，例如POCl 3，SOCl 2或COCl 2。在这项研究中，我们发现在O 2鼓泡下进行光辐照后，VR很容易从含有N，N-二甲基甲酰胺或N，N-二甲基乙酰胺的CHCl 3溶液中获得。通过产生气态HCl和CO 2可以高收率获得相应的Vilsmeier试剂作为副产物，以使其分离为适合通过X射线晶体学分析的结晶固体产物。利用使用双功能充当反应物和溶剂的CHCl 3的优点，这种按需光敏VR合成可用于一锅合成醛，酰氯，甲酸酯，酮，酯和酰胺。