非诺贝特 | 49580-59-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 非诺贝特
• 中文别名: (Z)-4-十一烯酸
• 英文名称: (Z)-4-undecenoic acid
• 英文别名: (4Z)-undec-4-enoic acid；(4Z)-undecenoic acid；cis-4-Undecensaeure；(Z)-undec-4-enoic acid
• CAS: 49580-59-8
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: KHDNXEYJITXOKI-FPLPWBNLSA-N

物化性质

• 沸点：
  291.9±9.0 °C(Predicted)
• 密度：
  0.929

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  非诺贝特 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正庚烷 、 乙基苯 为溶剂， 反应 4.5h， 生成 1-methyl-2-[(Z)-3'-decenyl]-4(1H)-quinolone
  参考文献：
  名称：

  Design, synthesis and antimycobacterial activities of 1-methyl-2-alkenyl-4(1H)-quinolones

  摘要：

  A series of 23 new 1-methyl-2-alkenyl-4(1H)quinolones have been synthesized and evaluated in vitro for their antimycobacterial activities against fast growing species of mycobacteria, such as Mycobacterium fortuitum, M. smegmatis and M. phlei. The compounds displayed good to excellent inhibition of the growth of the mycobacterial test strains with improved antimycobacterial activity compared to the hit compound, evocarpine. The most active compounds, which possessed chain length of 11-13 carbons at position-2 displayed potent inhibitory effects with an MIC value of 1.0 mg/L. In a human diploid embryonic lung cell line, MRC-5 cytotoxicity assay, the alkaloids showed weak to moderate cytotoxic activity. Biological evaluation of these evocarpine analogues on the less pathogenic fast growing strains of mycobacteria showed an interesting antimycobacterial profile and provided significant insight into the structure-activity relationships. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.060
• 作为产物：
  描述：

  正庚基三苯基溴化磷 在 双(三甲基硅烷基)氨基钾 、 戴斯-马丁氧化剂 、 sodium hydroxide 、 silver(l) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 非诺贝特
  参考文献：
  名称：

  两种蠕虫蛾（Carposinidae）酯信息素类似物的合成及生物学测试。

  摘要：

  合成了一系列用于类胡萝卜素的酯信息素类似物，并对其生物学活性进行了评估。这些类似物旨在利用在该家族中发现的（7 Z）-α酮11-酮的结构共性。对两种害虫种类进行了类似物测试：异花杂种和杂种Coscinoptycha improbana。其中的两个类似物，（2 Z）-壬烯基壬酸酯和（4 Z）-庚基十一烯酸酯，引起显着的脑电图反应。仅（4 Z）-十一碳烯酸庚酯在单个sensillum记录中对两种蛾类都给出了一致的响应。分别对这两种类似物以及与两种蛾类中每种信息素的结合进行了野外诱捕试验。蛾类物种对单独的任一类似物均未观察到吸引力。然而，当（4 Z）-十一碳烯酸十一碳酸酯与信息素偶联时，它对红花丝藻产生了强大的抑制作用，使雄蛾的诱捕量降低了95％以上。没有抑制作用的雄性蛾陷阱捕获在C. improbana。

  DOI：

  10.1021/acs.jafc.0c04131

文献信息

• NEW SYNTHETIC METHOD OF (Z)-4-ALKENOIC ACIDS USING RING-OPENING REACTION OF (Z)-4-HEXENOLIDE WITH ORGANOCOPPER REAGENT
  作者：Tamotsu Fujisawa、Kazuto Umezu、Masatoshi Kawashima

  DOI：10.1246/cl.1984.1795

  日期：1984.10.5

  (Z)-4-Hexenolide reacted regioselectively with diorganocuprates to give (Z)-4-alkenoic acids in high yields. Synthetic utility was demonstrated by the convenient synthesis of cis-jasmone.

  (Z)-4-己烯内酯与二有机铜酸盐发生区域选择性反应，以高产率得到 (Z)-4-链烯酸。顺式茉莉酮的方便合成证明了合成效用。
• Fe-Catalyzed Synthesis of (13Z)-Eicos-13-en-10-one, the Main Sex Pheromone Component of Carposina niponensis
  作者：R. N. Shakhmaev、A. Sh. Sunagatullina、V. V. Zorin

  DOI：10.1007/s10600-017-1925-3

  日期：2017.1

  (13Z)-Eicos-13-en-10-one, the main sex pheromone component of Carposina niponensis, was synthesized stereoselectively via Fe-catalyzed cross-coupling of ethyl (4Z)-5-chloropent-4-enoate with hexylmagnesiumbromide to give ethyl (4Z)-undec-4-enoate and repeated Fe-catalyzed cross-coupling of its acid chloride with nonylmagnesiumbromide.

  (4Z)-5-氯戊-4-烯酸乙酯与溴化己基镁在铁催化下发生交叉偶联，得到(4Z)-十一-4-烯酸乙酯，然后其酰氯与溴化壬基镁在铁催化下重复发生交叉偶联，立体选择性地合成了(13Z)-二十烷-13-烯-10-酮（尼泊金鲫的主要性信息素成分）。
• ONE-POT SYNTHESIS OF (<i>Z</i>)-4-ALKENOIC ACIDS
  作者：Tamotsu Fujisawa、Toshio Sato、Tatsuo Kawara、Kouichi Naruse

  DOI：10.1246/cl.1980.1123

  日期：1980.9.5

  The reaction of β-propiolactone with di-(Z)-1-alkenylcuprates, prepared from Grignard reagents, copper(I) iodide and acetylene, gave (Z)-4-alkenoic acids in high yields in one-pot operation.

  β-丙内酯与由格氏试剂、碘化铜（I）和乙炔制备的二-（Z）-1-烯基铜酸盐反应，在一锅操作中以高产率得到（Z）-4-烯酸。
• Chemistry and Photochemistry Attending the Inactivation of Escherichia coli .beta.-Hydroxydecanoyl Thiol Ester Dehydrase by an Acetylenic Diazoketone
  作者：Barry S. Henderson、Barbara S. Larsen、John M. Schwab

  DOI：10.1021/ja00091a001

  日期：1994.6

  beta-Hydroxydecanoyl thiol ester dehydrase from Escherichia coli, an enzyme that catalyzes both dehydration and allylic rearrangement reactions, has been shown previously to undergo mechanism-based inactivation by the acetylenic substrate analog 1-diazo-4-undecyn-2-one (DUO). Details of the chemistry and photochemistry of DUO are now presented. Analysis of DUO-inactivated dehydrase by N-15 NMR spectroscopy indicates that DUO quantitatively alkylates histidine-70. Long-wavelength photoirradiation leads to spectrophotometrically observable changes in the DUO-dehydrase adduct. The structural changes were characterized by a combination of methods. Samples of protein that had been inactivated with [1-C-13]-, [(2)-C-13]-, and [3-C-13]DUO were analyzed by C-13 NMR spectroscopy, both prior and subsequent to photoirradiation. By comparisons of the chemical shifts of the enriched atoms of the inactivator moiety with those of model compounds, it was confirmed that the alpha-diazoketone moiety is retained in DUO-inactivated dehydrase and that photoirradiation leads to Wolff rearrangement of the alpha-diazoketone moiety followed by attack of a nucleophile on the resulting ketene. Proteolytic degradation of photoirradiated; DUO-inactivated dehydrase gave peptides that were analyzed by Edman sequencing and by mass spectrometry. The results are consistent with a single protein modification (at H70), and attack on the ketene by water, leading to a carboxylic acid. Samples of intact native, DUO-inactivated, and photoirradiated, DUO-inactivated dehydrase were analyzed by electrospray ionization mass spectrometry, the results of which clearly support the hypothesis that the ketene suffers attack by water. In light of recent results from X-ray crystallography, it is proposed that the water that attacks the ketene is one of two bound water molecules with specific roles in the binding and/or catalytic turnover of substrate. A Michael addition-elimination mechanism is presented to explain the unexpected hydrolytic lability of the DUO-dehydrase adduct.
• FUJISAWA TAMOTSU; SATO TOSHIO; KAWARA TATSUO; NARUSE KOUICHI, CHEM. LETT., 1980, NO 9, 1123-1124
  作者：FUJISAWA TAMOTSU、 SATO TOSHIO、 KAWARA TATSUO、 NARUSE KOUICHI

  DOI：——

  日期：——