2-(1Z-pentadecenyl)furan | 208329-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(1Z-pentadecenyl)furan
• 英文别名: 2-[(Z)-pentadec-1-enyl]furan
• CAS: 208329-96-8
• 化学式: C₁₉H₃₂O
• 分子量: 276.462
• InChiKey: MAGFAZWZYBRMGQ-PEZBUJJGSA-N

物化性质

• 沸点：
  360.5±11.0 °C(Predicted)
• 密度：
  0.888±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(1Z-pentadecenyl)furan 以 苯 为溶剂， 反应 0.5h， 以57%的产率得到pentadeca-1'-enyl-2-furan
  参考文献：
  名称：

  摘要：

  Several insecticidal compounds have been identified by bioassay-driven fractionation of avocado, Persea americana Mill, idioblast cell oil. A flash chromatography fraction of the oil showed substantial toxicity to early instars of the generalist insect herbivore, Spodoptera exigua (Hubner) (100% mortality after seven days). Following further fractionation, five biologically active compounds, 2-(pentadecyl)furan, 2-(heptadecyl)furan, 2-(1E-penta-decenyl)furan, 2-(8Z,11Z-heptadecadienyl)furan, and the triglyceride triolein, were identified. Several minor components were also tentatively identified, including 2-(1Z-pentadecenyl)furan, 2-(1E-heptadecenyl)furan, and 2-(1E,8Z,11Z-heptadecatrienyl)furan. Several 2-alkylfurans of this type have been reported previously from avocado (Persea spp.) and have received the common name of avocadofurans. The major compounds were tested individually for toxic and growth inhibitory effects. Individually, the compounds had low to moderate toxicity. Of these, 2-(pentadecyl)furan had the greatest effects, with an LC50 value of 1031 mu g/g. At concentrations of 600 mu g/g or higher in diets, larval growth was inhibited by >70% compared to controls. The analogous 2-(heptadecyl)furan had an LC50 value of 1206 mu g/g, and also significantly reduced larval growth (>75% versus controls) at concentrations of > 600 mu g/g. The unsaturated analogs 2-(1E-pentadecenyl)furan and 2-(8Z, 11Z-heptadecadienyl)furan were less toxic. Triolein was only weakly toxic, with an LC50 value of 10,364 mu g/g diet. Larval growth was inhibited only at concentrations of 7000 mu g/g or higher. The potential of avocadofurans in insect control is discussed.

  DOI：

  10.1023/a:1022325601724
• 作为产物：
  描述：

  溴代十四烷 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium hydride 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 67.0h， 生成 2-(1Z-pentadecenyl)furan
  参考文献：
  名称：

  摘要：

  Several insecticidal compounds have been identified by bioassay-driven fractionation of avocado, Persea americana Mill, idioblast cell oil. A flash chromatography fraction of the oil showed substantial toxicity to early instars of the generalist insect herbivore, Spodoptera exigua (Hubner) (100% mortality after seven days). Following further fractionation, five biologically active compounds, 2-(pentadecyl)furan, 2-(heptadecyl)furan, 2-(1E-penta-decenyl)furan, 2-(8Z,11Z-heptadecadienyl)furan, and the triglyceride triolein, were identified. Several minor components were also tentatively identified, including 2-(1Z-pentadecenyl)furan, 2-(1E-heptadecenyl)furan, and 2-(1E,8Z,11Z-heptadecatrienyl)furan. Several 2-alkylfurans of this type have been reported previously from avocado (Persea spp.) and have received the common name of avocadofurans. The major compounds were tested individually for toxic and growth inhibitory effects. Individually, the compounds had low to moderate toxicity. Of these, 2-(pentadecyl)furan had the greatest effects, with an LC50 value of 1031 mu g/g. At concentrations of 600 mu g/g or higher in diets, larval growth was inhibited by >70% compared to controls. The analogous 2-(heptadecyl)furan had an LC50 value of 1206 mu g/g, and also significantly reduced larval growth (>75% versus controls) at concentrations of > 600 mu g/g. The unsaturated analogs 2-(1E-pentadecenyl)furan and 2-(8Z, 11Z-heptadecadienyl)furan were less toxic. Triolein was only weakly toxic, with an LC50 value of 10,364 mu g/g diet. Larval growth was inhibited only at concentrations of 7000 mu g/g or higher. The potential of avocadofurans in insect control is discussed.

  DOI：

  10.1023/a:1022325601724

文献信息

• LIPIDIC FURAN, PYRROLE, AND THIOPHENE COMPOUNDS FOR USE IN THE TREATMENT OF ATROPHIC VAGINITIS
  申请人：Avoscience, LLC

  公开号：US20170312246A1

  公开（公告）日：2017-11-02

  Provided herein are lipidic furan, pyrrole, and thiophene compounds, compositions, and methods using such compounds and compositions for the treatment of atrophic vaginitis. Specifically, the invention includes administering an effective amount of a compound of Formula I, I′, or I″, or a pharmaceutically acceptable composition, salt, isotopic analog, prodrug, or combination thereof, to a subject suffering from atrophic vaginitis.

  本文提供了脂质类呋喃、吡咯和噻吩化合物、组合物以及使用这些化合物和组合物治疗萎缩性阴道炎的方法。具体而言，本发明包括向患有萎缩性阴道炎的受试者投与化合物I、I'或I"的有效量，或者药学上可接受的组合物、盐、同位素类似物、前药或其组合物。
• Lipidic Furan, Pyrrole, and Thiophene Compounds for Treatment of Cancer, Neurological Disorders, and Fibrotic Disorders
  申请人：Avoscience, LLC

  公开号：US20140309274A1

  公开（公告）日：2014-10-16

  Compounds, methods, and compositions are provided for the treatment of cancer, neurological disorders, and fibrotic disorders. Specifically, the invention includes administering an effective amount of a compound of Formula I, II, or III, or a pharmaceutically acceptable composition, salt, isotopic analog, prodrug, or combination thereof, to a subject suffering from a cancer, neurological disorder, or fibrotic disorder.

  本发明提供了用于治疗癌症、神经系统疾病和纤维化疾病的化合物、方法和组合物。具体而言，该发明包括向患有癌症、神经系统疾病或纤维化疾病的受试者施用公式I、II或III的化合物、药学上可接受的组合物、盐、同位素类似物、前药或其组合的有效量。
• LIPIDIC FURAN, PYRROLE, AND THIOPHENE COMPOUNDS FOR TREATMENT OF CANCER, NEUROLOGICAL DISORDERS, AND FIBROTIC DISORDERS
  申请人：Avoscience, LLC

  公开号：US20160263080A1

  公开（公告）日：2016-09-15

  Compounds, methods, and compositions are provided for the treatment of cancer, neurological disorders, and fibrotic disorders. Specifically, the invention includes administering an effective amount of a compound of Formula I, II, or III, or a pharmaceutically acceptable composition, salt, isotopic analog, prodrug, or combination thereof, to a subject suffering from a cancer, neurological disorder, or fibrotic disorder.

  本发明提供了用于治疗癌症、神经系统疾病和纤维化疾病的化合物、方法和组合物。具体而言，本发明包括向患有癌症、神经系统疾病或纤维化疾病的受试者施用公式I、II或III的化合物或其药学上可接受的组合物、盐、同位素类似物、前药或其组合物的有效量。
• Lipidic furan, pyrrole, and thiophene compounds for treatment of cancer, neurological disorders, and fibrotic disorders
  申请人：Avoscience, LLC

  公开号：US10085962B2

  公开（公告）日：2018-10-02

  Compounds, methods, and compositions are provided for the treatment of cancer, neurological disorders, and fibrotic disorders. Specifically, the invention includes administering an effective amount of a compound of Formula I, II, or III, or a pharmaceutically acceptable composition, salt, isotopic analog, prodrug, or combination thereof, to a subject suffering from a cancer, neurological disorder, or fibrotic disorder.

  本发明提供了用于治疗癌症、神经系统疾病和纤维化疾病的化合物、方法和组合物。具体来说，本发明包括向患有癌症、神经系统疾病或纤维化疾病的受试者施用有效量的式 I、II 或 III 化合物或其药学上可接受的组合物、盐、同位素类似物、原药或其组合物。
• Lipidic furan, pyrrole, and thiophene compounds for use in the treatment of atrophic vaginitis
  申请人：Avoscience, LLC

  公开号：US10905673B2

  公开（公告）日：2021-02-02

  Provided herein are lipidic furan, pyrrole, and thiophene compounds, compositions, and methods using such compounds and compositions for the treatment of atrophic vaginitis. Specifically, the invention includes administering an effective amount of a compound of Formula I, I′, or I″, or a pharmaceutically acceptable composition, salt, isotopic analog, prodrug, or combination thereof, to a subject suffering from atrophic vaginitis.

  本发明提供了脂质呋喃、吡咯和噻吩化合物、组合物以及使用此类化合物和组合物治疗萎缩性阴道炎的方法。具体来说，本发明包括向患有萎缩性阴道炎的受试者施用有效量的式Ⅰ、Ⅰ′或Ⅰ″化合物或药学上可接受的组合物、盐、同位素类似物、原药或其组合物。