p-[N-methyl-N-(trifluoroacetyl)amino]benzoyl chloride | 95063-86-8

• 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: p-[N-methyl-N-(trifluoroacetyl)amino]benzoyl chloride
• 英文别名: Benzoyl chloride, 4-[methyl(2,2,2-trifluoroacetyl)amino]-；4-[methyl-(2,2,2-trifluoroacetyl)amino]benzoyl chloride
• CAS: 95063-86-8
• 化学式: C₁₀H₇ClF₃NO₂
• 分子量: 265.619
• InChiKey: IUAYDJYZQYUZOK-UHFFFAOYSA-N

物化性质

• 沸点：
  287.4±40.0 °C(Predicted)
• 密度：
  1.444±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  p-[N-methyl-N-(trifluoroacetyl)amino]benzoyl chloride 在 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 (S)-4-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-isopropylcarbamoyl-butyric acid tert-butyl ester
  参考文献：
  名称：

  Antonjuk, David J.; Boadle, Deborah K.; Cheung, H.T.Andrew, Journal of the Chemical Society. Perkin transactions I, 1984, p. 1989 - 2004

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氨基苯甲酸 在 四氯化碳 、 三苯基膦 、 三氟乙酸酐 作用下， 以 乙腈 为溶剂， 反应 0.33h， 生成 p-[N-methyl-N-(trifluoroacetyl)amino]benzoyl chloride
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of 2-Pyrazinylcarboxamido- benzoates and β-Ionylideneacetamidobenzoates with Retinoidal Activity

  摘要：

  The structure-activity relationships of two series of novel retinoids (2-pyrazinylcarboxamidobenzoates and beta-ionylideneacetamidobenzoates) have been investigated by evaluating their ability to induce differentiation in both human promyelocytic leukemia (HL60) cells and mouse embryonal carcinoma (P19) cells. The most active compound (ED50 = 8.3 x 10(-9) M) of the 2-pyrazinylcarboxamidobenzoates is 4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylquinoxalyl)-carboxamido]benzoic acid (9u), while the most active analogue of the beta-ionylideneacetamidobenzoates is 4-[3-methyl-5-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-(2E,4E)-pentadienamido]benzoic acid (10a, ED50 = 3.2 x 10(-8) M). Our studies identify an absolute requirement for the carboxylic acid moiety on the aromatic ring to be para relative to the amide linkage for activity. Benzoate substitutions in the ortho position relative to the terminal carboxylate (9d,k,r) are well-tolerated; however, a methoxy substituent meta relative to the terminal carboxylate gives rise to only weakly active analogues (9x). Conformational studies (NMR, X-ray crystallography) of the 2-pyrazinylcarboxamidobenzoates indicate that the preferred conformation exhibits a trans-amide bond and an internal hydrogen bond between the quinoxaline N1 and HN amide which locks the torsional angle between C2 and CO in the s-trans conformation. N-Methylation (9y) results in loss of activity. Studies indicate that there is now a cis-amide bond present which redirects the carboxylate toward the pharmacophoric gem-dimethyl groups. The distance between the gem-dimethyl group and the terminal carboxylate appears to be too short to activate the retinoid receptor. N-Methylation in the beta-ionylideneacetamidobenzoate series (10c) also results in the formation of a cis-amide bond and loss of activity.

  DOI：

  10.1021/jm9801354

文献信息

• .omega.-[(.omega.-Arylalkyl)aryl]alkanoic acids: a new class of specific LTA4 hydrolase inhibitors
  作者：Richard Labaudiniere、Gerd Hilboll、Alicia Leon-Lomeli、Hans Heiner Lautenschlaeger、Michael Parnham、Peter Kuhl、Norbert Dereu

  DOI：10.1021/jm00095a010

  日期：1992.8

  The synthesis and structure-activity profile of a new class of potent and specific LTA4 hydrolase inhibitors are described. Many compounds of this series of omega-[5-(omega-arylalkyl)-2-thienyl]- and omega-[4-(omega-arylalkyl)phenyl]alkanoic acids were found to be potent in vitro inhibitors of the LTB4 production by porcine leukocytes with IC50 ranging from 1 to 10 microM. The side-chain lengths were

  描述了新型有效和特异性LTA4水解酶抑制剂的合成和结构活性图。发现该系列的ω-[5-（ω-芳基烷基）-2-噻吩基]-和ω-[4-（ω-芳基烷基）苯基]链烷酸的许多化合物是有效的体外抑制LTB4产生的抑制剂猪白细胞，IC50为1至10 microM。侧链的长度对于最佳活性至关重要。亲脂性和供电子性取代基在苯系列末端芳香环上的取代作用大大增强了LTA4水解酶的抑制能力。另一方面，在噻吩系列中，这种取代对LTA4水解酶抑制的影响很小。在羧酸侧链中通过羰基或羟基的官能化导致效力较低的化合物。通过在羧酸侧链的β位插入一个氧原子，可获得代谢稳定的LTA4水解酶抑制剂RP64966。向大鼠口服施用RP64966后，发现血浆提取物显示出对LTB4生物合成的有效抑制作用（在5 mg / kg，口服时抑制40％）。
• Simple and Practical Conversion of Benzoic Acids to Phenols at Room Temperature
  作者：Wenzhang Xiong、Qiu Shi、Wenbo H. Liu

  DOI：10.1021/jacs.2c07529

  日期：2022.8.31

  Phenols are important organic molecules because they have found widespread applications in many fields. Herein, an efficient and practical approach to prepare phenols from benzoic acids via simple organic reagents at room temperature is reported. This approach is compatible with various functional groups and heterocycles and can be easily scaled up. To demonstrate its synthetic utility, bioactive molecules

  酚类是重要的有机分子，因为它们在许多领域都有广泛的应用。本文报道了一种在室温下通过简单的有机试剂从苯甲酸制备酚类的有效实用方法。这种方法与各种官能团和杂环兼容，并且可以轻松放大。为了证明其合成效用，生物活性分子和不对称六芳基苯已通过利用这种转变作为战略步骤来制备。机理研究表明，关键的迁移步骤涉及游离碳正离子而不是自由基中间体。考虑到苯甲酸的丰富性和酚类的实用性，预计该方法将在有机合成中得到广泛的应用。
• Methotrexate Analogues. 25. Chemical and Biological Studies on the γ-tert-Butyl Esters of Methotrexate and Aminopterin
  作者：Andre Rosowsky、James H. Freisheim、Henry Bader、Ronald A. Forsch、Sandra S. Susten、Carol A. Cucchi、Emil Frie

  DOI：10.1021/jm50001a021

  日期：1985.5

  gamma-tert-Butylaminopterin (gamma-tBAMT), the first example of an aminopterin (AMT) gamma-monoester, was synthesized, and new routes to the known N10-methyl analogue gamma-tert-butyl methotrexate (gamma-tBMTX) were developed. The inhibitory effects of gamma-tBAMT on the activity of purified dihydrofolate reductase (DHFR) from L1210 murine leukemia cells, the growth of L1210 cells and CEM human leukemic lymphoblasts in suspension culture, and the growth of several lines of human squamous cell carcinoma of the head and neck in monolayer culture were compared with the effects of gamma-tBMTX and the parent acids AMT and methotrexate (MTX). Patterns of cross-resistance to gamma-tBAMT, gamma-tBMTX, and AMT among several MTX-resistant cell lines were examined. In vivo antitumor activities of gamma-tBAMT and gamma-tBMTX were compared in mice with L1210 leukemia. While the activity of gamma-tBAMT was very close to that of gamma-tBMTX in the DHFR inhibition assay, the AMT ester was more potent than the MTX ester against cells in culture and against L1210 leukemia in vivo. Only partial cross-resistance was shown against gamma-tBMTX and gamma-tBAMT in cultured cells that were resistant to MTX by virtue of a transport defect or a combination of defective transport and elevated DHFR activity.