(E)-3-hexadecen-2-one | 183163-39-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-3-hexadecen-2-one
• 英文别名: 3-hexadecen-2-one；(E)-hexadec-3-en-2-one
• CAS: 183163-39-5
• 化学式: C₁₆H₃₀O
• 分子量: 238.414
• InChiKey: OSXJFKGXCJXRJC-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-propylisatoic anhydride 、 (E)-3-hexadecen-2-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以49%的产率得到1-propyl-2-[(1E)-tetradecenyl]-4-(1H)-quinolone
  参考文献：
  名称：

  Synthesis of N-substituted 2-[(1E)-alkenyl]-4-(1H)-quinolone derivatives as antimycobacterial agents against non-tubercular mycobacteria

  摘要：

  In an effort to improve biological activities and to examine antimycobacterial-lipophilicity relationships of 2-[(1E)-alkenyl)]-4-(1H)-quinolones, we have synthesized a series of 30 quinolones by introducing several alkyl groups, an alkenyl and an alkynyl group at N-1. All synthetic compounds were first tested in vitro against Mycobacterium smegmatis and the most active compounds (MIC values similar to 3.0-7.0 mu M) were further examined against three other rapidly growing strains of mycobacteria using a microtiter broth dilution assay. The Clog P values of the synthetic compounds were calculated to provide an estimate of their lipophilicity. Compounds 18e, 19a and 19b displayed the most potent inhibitory effect against M. smegmatis mc(2)155 with an MIC value of similar to 1.5 mu M, which was twenty fold and thirteen fold more potent than isoniazid and ethambutol, respectively. On the other hand, compounds 17e, 18e and 19a were most active against Mycobacterium fortuitum and Mycobacterium phlei with an MIC value of similar to 3.0 mu M. In the human diploid embryonic lung cell line MRC-5 cytotoxicity assay, the derivatives showed moderate to strong cytotoxic activity. Although the antimycobacterial activity of our synthetic compounds could not be correlated with the calculated log P values, an increase in lipophilicity enhances the antimycobacterial activity and C-13-C-15 total chain length at positions 1 and 2 is required to achieve optimal inhibitory effect against the test strains. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.062
• 作为产物：
  描述：

  十三醛 、 丙酮 在 哌啶 、 溶剂黄146 作用下， 反应 5.5h， 以71%的产率得到(E)-3-hexadecen-2-one
  参考文献：
  名称：

  Antimicrobial activity of long-chain (E)-3-alken-2-ones

  摘要：

  （E）-3-12-脱甲基戊二酮是从野兔（Odocoileus hemionus columbianus）的指间腺中发现的一种化合物，已被证明能够抑制细菌和真菌的生长。制备了该化合物的同源化合物，并进行抗微生物活性筛选。对于真菌Trichophyton mentagrophytes，（E）-3-14-脱甲基戊二酮的最低抑菌浓度（MIC）为12.5 μg/mL；对于细菌Propionibacterium acnes，（E）-3-17-脱甲基戊二酮的MIC为3.13 μg/mL。（C）2010 Elsevier Ltd. All rights reserved。

  DOI：

  10.1016/j.bmcl.2010.02.016

文献信息

• Synthesis and Antibacterial Evaluation of a New Series of N-Alkyl-2-alkynyl/(E)-alkenyl-4-(1H)-quinolones
  作者：Abraham Wube、Juan-David Guzman、Antje Hüfner、Christina Hochfellner、Martina Blunder、Rudolf Bauer、Simon Gibbons、Sanjib Bhakta、Franz Bucar

  DOI：10.3390/molecules17078217

  日期：——

  To gain further insight into the structural requirements of the aliphatic group at position 2 for their antimycobacterial activity, some N-alkyl-4-(1H)-quinolones bearing position 2 alkynyls with various chain length and triple bond positions were prepared and tested for in vitro antibacterial activity against rapidly-growing strains of mycobacteria, the vaccine strain Mycobacterium bovis BCG, and

  为了进一步了解 2 位脂肪族基团的抗分枝杆菌活性的结构要求，一些 N-烷基-4-(1H)-喹诺酮类在 2 位具有不同链长和三键位置的炔基被制备和测试。对快速生长的分枝杆菌菌株、疫苗菌株牛分枝杆菌 BCG 和耐甲氧西林金黄色葡萄球菌菌株 EMRSA-15 和 -16 的体外抗菌活性。还评估了化合物对结核分枝杆菌的 ATP 依赖性 MurE 连接酶的抑制作用。对偶发分枝杆菌和耻垢分枝杆菌的最低 MIC 值为 0.5 mg/L (1.2–1.5 µM)。这些化合物在 100 µM 浓度下对人肺成纤维细胞系 MRC-5 没有或只有微弱的毒性。喹诺酮衍生物对流行的 MRSA 菌株（EMRSA-15 和 -16）表现出显着的活性，MIC 值为 2–128 mg/L（5.3–364.7 µM），对牛分枝杆菌 BCG 的 MIC 值为 25 mg/L (66.0–77.4 µM)。此外，这些化合物抑制结核分枝杆菌的
• Mixtures having (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole)(Ambrocenide®)
  申请人：SYMRISE AG

  公开号：US10526563B2

  公开（公告）日：2020-01-07

  The present invention relates in particular to a mixture comprising or at least essentially consisting of compound of formula (Ia) and (beta,beta-(4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole) of the formula (Ib), wherein the weight ratio of the compound of the formula (Ia) to the compound of the formula (Ib) in the mixture is in the range from 90:10 to 99:1. The present invention further relates to a method for producing such a mixture, to new odorant and/or aroma substance compositions, and to the use of a mixture of the invention (a) for masking or diminishing the one or more unpleasant olfactory impressions of one or more unpleasantly smelling substances, and/or (b) for intensifying the one or more pleasant olfactory impressions of one or more pleasantly smelling substances.

  本发明尤其涉及一种混合物，该混合物包含或至少基本上包含式（Ia）化合物和式（Ib）化合物（β,β-(4aR,5R,7aS,9R)-八氢-2,2,5,8,8,9a-六甲基-4H-4a、式(Ib)的 9-甲桥氮杂环戊烯并(5,6-d)-1,3-二氧杂环戊烯，其中混合物中式(Ia)化合物与式(Ib)化合物的重量比在 90：10 至 99:1。本发明还涉及生产这种混合物的方法、新的气味剂和/或芳香物质组合物，以及本发明混合物在以下方面的用途：(a)掩盖或减少一种或多种气味难闻物质的一种或多种难闻嗅觉印象，和/或(b)增强一种或多种气味宜人物质的一种或多种宜人嗅觉印象。
• TOPICAL ANTIMICROBIAL AGENTS
  申请人：Research Corporation Technologies, Inc

  公开号：EP0814660A1

  公开（公告）日：1998-01-07
• ÖL IN WASSER-EMULSIONEN MIT EINEM GEHALT AN 4-HYDROXYACETOPHENON UND ANIONISCHEN EMULGATOREN
  申请人：Symrise AG

  公开号：EP3122316A1

  公开（公告）日：2017-02-01
• New mixtures having (4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole)(Ambrocenide®)
  申请人：SYMRISE AG

  公开号：US20170114299A1

  公开（公告）日：2017-04-27

  The present invention relates in particular to a mixture comprising or at least essentially consisting of compound of formula (Ia) and (beta,beta-(4aR,5R,7aS,9R)-octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methanoazuleno(5,6-d)-1,3-dioxole) of the formula (Ib), wherein the weight ratio of the compound of the formula (Ia) to the compound of the formula (Ib) in the mixture is in the range from 90:10 to 99:1. The present invention further relates to a method for producing such a mixture, to new odorant and/or aroma substance compositions, and to the use of a mixture of the invention (a) for masking or diminishing the one or more unpleasant olfactory impressions of one or more unpleasantly smelling substances, and/or (b) for intensifying the one or more pleasant olfactory impressions of one or more pleasantly smelling substances.