methyl 2-trifluoromethyltetradecanoate | 693244-98-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 2-trifluoromethyltetradecanoate
• 英文别名: Methyl 2-(trifluoromethyl)tetradecanoate
• CAS: 693244-98-3
• 化学式: C₁₆H₂₉F₃O₂
• 分子量: 310.4
• InChiKey: NRCREBXIILDBMR-UHFFFAOYSA-N

物化性质

• 沸点：
  322.4±37.0 °C(Predicted)
• 密度：
  0.992±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-trifluoromethyltetradecanoate 在 palladium 10% on activated carbon 、 氢气 、 二正丁基氧化锡 作用下， 以 乙酸乙酯 为溶剂， 150.0 ℃ 、101.33 kPa 条件下， 反应 19.0h， 生成 2-Trifluoromethyltetradecanoic acid
  参考文献：
  名称：

  前列腺肿瘤成像的新分子标记：2-亚甲基取代脂肪酸作为新型AMACR抑制剂的研究

  摘要：

  前列腺癌的发展与脂肪酸代谢的改变有关。α-甲基酰基辅酶A外消旋酶（AMACR）是一种过氧化物酶体和线粒体酶，催化一系列α-甲基酰基辅酶A硫酯的（S）/（R）异构体之间的相互转化。AMACR参与膳食支链脂肪酸和胆汁酸中间体的β-氧化。它在前列腺（95％以上），结肠（92％）和乳腺癌（44％）中高表达，但在相应的正常或增生组织中却没有高表达。因此，针对AMACR的靶向可能是前列腺癌和其他一些癌症的分子成像和治疗的新策略。未标记的2-亚甲基酰基-CoA硫酯（12 a – c）被设计为AMACR结合配体。测试了硫酯抑制（25 R）-THC-CoA的AMACR介导的差向异构化的能力，发现它们是强AMACR抑制剂。放射性碘（E）131 I-13碘-2-甲基对苯二甲酸12烯酸（131 I- 7 c）与AMACR阳性前列腺肿瘤细胞（LNCaP，LNCaP C4-2wt和DU145）相比均具有优先保留AMACR基因敲除LNCaP

  DOI：

  10.1002/chem.201003176
• 作为产物：
  描述：

  methyl 2-trifluoromethyltetradec-2-enoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以94%的产率得到methyl 2-trifluoromethyltetradecanoate
  参考文献：
  名称：

  Design, Synthesis, and In Vitro Testing of α-Methylacyl-CoA Racemase Inhibitors

  摘要：

  The enzyme alpha-methylacyl-CoA racemase (AMACR) is overexpressed in prostate, colon, and other cancers and has been partially validated as a potential therapeutic target by siRNA knockdown of the AMACR gene. Analogs of the natural substrate branched chain alpha-methylacyl coenzyme A esters, possessing one or more beta-fluorine atoms, have been synthesized using Wittig, conjugate addition, and asymmetric aldol reactions and found to be reversible competitive inhibitors. Each diastereomer of the previously reported inhibitor ibuprofenoyl-CoA was also tested. The compounds had K-i values of 0.9-20 mu M and are the most potent inhibitors yet known. The presence of beta-fluorine on the alpha-methyl group or the acyl chain results in a significant lowering of the K-i value compared with nonfluorinated analogs, and this is attributed to a lowering of the pK(a) of the alpha-proton, facilitating enolization and binding. Several of the CoA ester inhibitors were formed by incubating the free carboxylic acid precursors with cell free extracts and CoA. alpha-Trifluoromethyltetradecanoic acid, the precursor to the most potent inhibitor, was shown to inhibit growth of cancer cell lines PC3, CWR22 Rv1, and Du145 in a dose-dependent manner and could be related to the expression level of AMACR.

  DOI：

  10.1021/jm0702377

文献信息

• The first general method for α-trifluoromethylation of carboxylic acids using BrF₃
  作者：Aviv Hagooly、Shlomo Rozen

  DOI：10.1039/b315705a

  日期：——

  2-Carbomethoxy-1,1-bis(methylsulfide)-1-alkenes, easily made from carboxylic acids, CS2 and MeI, were treated with BrF3 producing eventually the desired α-trifluoromethyl carboxylate derivatives – RCH(CF3)COOR′ – in good yields.

  2-Carbomethoxy-1,1-bis(methylsulfide)-1-alkenes 很容易由羧酸、CS2 和 MeI 制成，用 BrF3 处理后，最终会以良好的收率生成所需的δ-三氟甲基羧酸衍生物 RCH(CF3)COORâ² 。