campest-5-en-3-one | 57708-06-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: campest-5-en-3-one
• 英文别名: (8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5,6-dimethylheptan-2-yl]-10,13-dimethyl-1,2,4,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 57708-06-2
• 化学式: C₂₈H₄₆O
• 分子量: 398.673
• InChiKey: ATIPVUGMJZAJPC-IMUDCKKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  campest-5-en-3-one 在 palladium on activated charcoal Wakogel C-300 、 氢气 、 氧气 、 silica gel 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 121.0h， 生成 5-epi-campestane-3,6-dione
  参考文献：
  名称：

  Synthesis of 6-oxy functionalized campest-4-en-3-ones: efficient hydroperoxidation at C-6 of campest-5-en-3-one with molecular oxygen and silica gel

  摘要：

  As a reference compound library for the investigation of biosynthesis of brassinosteroids, focused on a pathway from campesterol (1) to campestanol (2), 6-oxy functionalized campest-4-en-3-ones as well as campest-5-en-3-one (7) and campestane-3,6-dione were prepared from 1. Oxidation of 1 with pyridinium chlorochromate buffered by calcium carbonate gave 5-en-3-one (7) in 76% yield. Treatment of 7 with silica gel under an oxygen atmosphere in ethyl ether at room temperature produced efficient hydroperoxidation at the C-6 position to give 6 alpha-hydroperoxycampest-4-en-3-one and 6 beta-hydroperoxycampest-4-en-3-one in 34% and 49% yields, respectively. These compounds were converted to 6 alpha-hydroxycampest-4-en-3-one and 6 beta-hydroxycampest-4-en-3-one by reduction with triethyl phosphite. This provided the first example of the practical use of hydroperoxidation at C-6 of a Delta(5(6))-unsaturated 3-oxo-steroid with molecular oxygen and silica gel. On the other hand, oxidation of 1 with pyridinium chlorochromate in the absence of calcium carbonate gave campest-4-ene-3,6-dione in 64% yield. This compound was then converted in a highly stereoselective manner to campestane-3,6-dione with A/B trans ring junction by reduction with titanium (III) chloride in 85% yield.

  DOI：

  10.1016/s0039-128x(00)00105-7
• 作为产物：
  描述：

  菜油甾醇 在 3 A molecular sieve 、 pyridinium chlorochromate 、 calcium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以76%的产率得到campest-5-en-3-one
  参考文献：
  名称：

  Synthesis of 6-oxy functionalized campest-4-en-3-ones: efficient hydroperoxidation at C-6 of campest-5-en-3-one with molecular oxygen and silica gel

  摘要：

  As a reference compound library for the investigation of biosynthesis of brassinosteroids, focused on a pathway from campesterol (1) to campestanol (2), 6-oxy functionalized campest-4-en-3-ones as well as campest-5-en-3-one (7) and campestane-3,6-dione were prepared from 1. Oxidation of 1 with pyridinium chlorochromate buffered by calcium carbonate gave 5-en-3-one (7) in 76% yield. Treatment of 7 with silica gel under an oxygen atmosphere in ethyl ether at room temperature produced efficient hydroperoxidation at the C-6 position to give 6 alpha-hydroperoxycampest-4-en-3-one and 6 beta-hydroperoxycampest-4-en-3-one in 34% and 49% yields, respectively. These compounds were converted to 6 alpha-hydroxycampest-4-en-3-one and 6 beta-hydroxycampest-4-en-3-one by reduction with triethyl phosphite. This provided the first example of the practical use of hydroperoxidation at C-6 of a Delta(5(6))-unsaturated 3-oxo-steroid with molecular oxygen and silica gel. On the other hand, oxidation of 1 with pyridinium chlorochromate in the absence of calcium carbonate gave campest-4-ene-3,6-dione in 64% yield. This compound was then converted in a highly stereoselective manner to campestane-3,6-dione with A/B trans ring junction by reduction with titanium (III) chloride in 85% yield.

  DOI：

  10.1016/s0039-128x(00)00105-7

文献信息

• HYPOGLYCEMIC AGENT
  申请人：Riken

  公开号：EP1413308A1

  公开（公告）日：2004-04-28

  A hypoglycemic agent comprising a compound selected from the group consisting of 24-alkylcholestan-3-ones and 24-alkylcholesten-3-ones (for example, 24-alkylcholestan-3-ones, 24-alkylcholestmonoen-3-ones, 24-alkylcholestdien-3-ones, 24-alkylcholesttrien-3-ones, or 24-alkylcholesttetraen-3-ones, preferably 5-campesten-3-one) as an active ingredient. The agent can be used for improvement of hyperglycemia resulting from diseases such as diabetes, and can be used as a safe medicament without side effects such as hypoglycemia or diarrhea.

  一种降血糖药剂，包含一种选自 24-烷基胆甾烷-3-酮和 24-烷基胆甾烯-3-酮（例如 24-烷基胆甾烷-3-酮、24-烷基胆甾烯-3-酮、24-烷基胆甾烯-3-酮、24-烷基胆甾烯三烯-3-酮或 24-烷基胆甾烯四烯-3-酮，优选 5-坎普烯-3-酮）组成的组的化合物作为活性成分。该制剂可用于改善糖尿病等疾病引起的高血糖，并且可作为安全的药物使用，不会产生低血糖或腹泻等副作用。
• DRUGS, FOOD OR DRINK FOR IMPROVING PANCREATIC FUNCTIONS
  申请人：MORINAGA MILK INDUSTRY CO., LTD.

  公开号：EP1808175A1

  公开（公告）日：2007-07-18

  Compounds such as 4-methylcholest-7-en-3-ol, 4-methylergost-7-en-3-ol and 4-methylstigmast-7-en-3-ol which have an activity for improving pancreatic function are used as an active ingredient of a pancreas function improving drug and food or drink.

  4-甲基胆甾-7-烯-3-醇、4-甲基麦角甾-7-烯-3-醇和 4-甲基豆甾-7-烯-3-醇等化合物具有改善胰腺功能的活性，可用作改善胰腺功能的药物和食品或饮料的活性成分。
• NOVEL USE OF PHYTOSTENONE
  申请人：Daisankasei Co., Ltd.

  公开号：EP3845232A1

  公开（公告）日：2021-07-07

  According to the present invention, a transdermal absorbent for reducing a subcutaneous fat is provided, which comprises phytostenone. Accordingly, a method for further reducing a subcutaneous fat can be provided.

  根据本发明，提供了一种用于减少皮下脂肪的透皮吸收剂，其中包括植物生长激素。相应地，还可以提供一种进一步减少皮下脂肪的方法。
• Medicament for treating obesity and improving lipid metabolism
  申请人：RIKEN

  公开号：US20020086855A1

  公开（公告）日：2002-07-04

  A medicament for preventive and therapeutic treatment of obesity and a disease with abnormal lipid metabolism which comprises a 24-alkylcholest-5-en-3-one as an active ingredient.

  一种用于预防和治疗肥胖症和脂质代谢异常疾病的药物，其活性成分为 24-烷基胆甾-5-烯-3-酮。
• DAS5, a P450 protein involved in the brassinosteroid biosynthesis pathway in plants
  申请人：——

  公开号：US20030150025A1

  公开（公告）日：2003-08-07

  The present invention provides a cytochrome P450-encoding gene, DAS5, as well as an altered gene, das5-D, which are involved in the synthesis of the plant steroid hormone brassinolide. The das5-D mutant has an insertion of a T-DNA containing transcriptional enhancers into its promoter region. Overexpression of the mutant thus produces large amounts of DAS5 transcript. The expression of this das5-D mutation or overexpression of the DAS5 gene in transgenic plants causes such plants to become significantly larger and more robust than their wild-type counterparts, thus increasing plant yields.

  本发明提供了一种细胞色素 P450 编码基因 DAS5 以及一种改变基因 das5-D，它们参与植物甾体激素黄铜内酯的合成。das5-D 突变体的启动子区域插入了一个含有转录增强子的 T-DNA 。因此，过量表达该突变体会产生大量的 DAS5 转录本。在转基因植物中表达这种 das5-D 突变体或过量表达 DAS5 基因，会使这些植物比野生型植物明显更大、更健壮，从而提高植物产量。