dimethyl gibberellenate (3β-OH) | 79232-40-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: dimethyl gibberellenate (3β-OH)
• 英文别名: methyl gibberellate；Gibberellensaeure-dimethylester；Gibberellen-saeure-methylester；(1S,2S,7S,9aR,10S,10aS)-Dimethyl 2,7-dihydroxy-1-methyl-8-methylene-2,5,6,7,8,9,10,10a-octahydro-1H-7,9a-methanobenzo[a]azulene-1,10-dicarboxylate；dimethyl (1R,2S,3S,4S,5S,12S)-5,12-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.01,9.03,8]pentadeca-6,8-diene-2,4-dicarboxylate
• CAS: 79232-40-9
• 化学式: C₂₁H₂₆O₆
• 分子量: 374.434
• InChiKey: ZLHPVNZIBYTAEZ-DPMXFYLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl gibberellenate (3β-OH) 在 4-二甲氨基吡啶 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 C₂₅H₃₀O₉
  参考文献：
  名称：

  COMPLEX AND STRUCTURALLY DIVERSE COMPOUNDS

  摘要：

  这项发明提供了一种新颖、通用且简便的策略，用于创造具有高结构和立体化学复杂性的小分子。该方法的方面包括系统地应用于快速将易得的天然产物转化为具有多样分子结构的结构复杂化合物的环系统失真反应。通过评估化学性质，包括sp3碳的分数、ClogP和立体中心的数量，这些化合物被证明比标准筛选集合中的化合物显着更复杂和多样化。这种方法是通过来自三个不同结构类别的天然产物（赤霉酸、肾上腺酮和奎宁）来展示的，并描述了将该策略应用于任何合适的天然产物的方法。

  公开号：

  US20150274638A1
• 作为产物：
  描述：

  赤霉素 、 alkaline earth salt of/the/ methylsulfuric acid 在 甲醇 、 四氰基乙烯 、 cesium fluoride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 dimethyl gibberellenate (3β-OH)
  参考文献：
  名称：

  Hanson, James R.; Uyanik, Cavit, Journal of Chemical Research, Miniprint, 1998, # 11, p. 2850 - 2861

  摘要：

  DOI：

文献信息

• Competition between singlet state photoreduction and triplet state photodimerization of dimethyl 3-dehydrogibberellenate
  作者：H.K. Al-Ekabi、G.A.W. Derwish、G. Adam、K. Schreiber

  DOI：10.1016/s0040-4020(01)92050-2

  日期：1981.1

  Photolysis of dilute solutions (10-4M) of dimethyl 3-dehydrogibberellenate 1, in MeOH, EtOH, i-PrOH, t-BuOH and 2, 2, 2-trifluoroethanol, showed that while the last two solutions underwent photodimerization reactions only; the other solutions gave photoreduction products 2 and 3, besides some photodimerization product. It is further shown that while photodimerization proceeded through triplet excited

  3-脱氢赤霉烯酸二甲酯1的稀溶液（10 -4 M）在MeOH，EtOH，i-PrOH，t-BuOH和2，2，2-三氟乙醇中的光解表明，虽然后两种溶液仅进行了光二聚反应；但最后两种溶液仅进行了光二聚反应。除某些光二聚化产物外，其他解决方案还产生了光还原产物2和3。进一步表明，尽管光二聚化通过三重激发态进行，但是令人惊奇的是，光还原仅通过单重激发态进行。
• Complex and structurally diverse compounds
  申请人：The Board of Trustees of the University of Illinois

  公开号：US10800730B2

  公开（公告）日：2020-10-13

  The invention provides a novel, general, and facile strategy for the creation of small molecules with high structural and stereochemical complexity. Aspects of the methods include ring system distortion reactions that are systematically applied to rapidly convert readily available natural products to structurally complex compounds with diverse molecular architectures. Through evaluation of chemical properties including fraction of sp3 carbons, ClogP, and the number of stereogenic centers, these compounds are shown to be significantly more complex and diverse than those in standard screening collections. This approach is demonstrated with natural products (gibberellic acid, adrenosterone, and quinine) from three different structural classes, and methods are described for the application of this strategy to any suitable natural product.

  本发明提供了一种新颖、通用和简便的策略，用于制造具有高结构和立体化学复杂性的小分子。该方法的各个方面包括系统地应用环系畸变反应，将容易获得的天然产物快速转化为具有不同分子结构的结构复杂的化合物。通过对化学特性（包括 sp3 碳的比例、ClogP 和立体中心的数量）进行评估，这些化合物的复杂性和多样性明显高于标准筛选集合中的化合物。该方法通过三种不同结构类别的天然产物（赤霉素、肾上腺甾酮和奎宁）进行了演示，并介绍了将该策略应用于任何合适的天然产物的方法。
• Baynham, Mark K.; Hanson, James R.; Hitchcock, Peter B., Journal of Chemical Research, Miniprint, 1990, # 5, p. 1079 - 1094
  作者：Baynham, Mark K.、Hanson, James R.、Hitchcock, Peter B.、Oliveira, Bras H. de

  DOI：——

  日期：——
• [EN] COMPLEX AND STRUCTURALLY DIVERSE COMPOUNDS<br/>[FR] COMPOSÉS COMPLEXES ET DE STRUCTURES DIVERSES
  申请人：HERGENROTHER PAUL J

  公开号：WO2013142873A2

  公开（公告）日：2013-09-26

  The invention provides a novel, general, and facile strategy for the creation of small molecules with high structural and stereochemical complexity. Aspects of the methods include ring system distortion reactions that are systematically applied to rapidly convert readily available natural products to structurally complex compounds with diverse molecular architectures. Through evaluation of chemical properties including fraction of sp3 carbons, ClogP, and the number of stereogenic centers, these compounds are shown to be significantly more complex and diverse than those in standard screening collections. This approach is demonstrated with natural products (gibberellic acid, adrenosterone, and quinine) from three different structural classes, and methods are described for the application of this strategy to any suitable natural product.
• COMPLEX AND STRUCTURALLY DIVERSE COMPOUNDS
  申请人：The Board of Trustees of the University of Illinois

  公开号：US20150274638A1

  公开（公告）日：2015-10-01

  The invention provides a novel, general, and facile strategy for the creation of small molecules with high structural and stereochemical complexity. Aspects of the methods include ring system distortion reactions that are systematically applied to rapidly convert readily available natural products to structurally complex compounds with diverse molecular architectures. Through evaluation of chemical properties including fraction of sp 3 carbons, ClogP, and the number of stereogenic centers, these compounds are shown to be significantly more complex and diverse than those in standard screening collections. This approach is demonstrated with natural products (gibberellic acid, adrenosterone, and quinine) from three different structural classes, and methods are described for the application of this strategy to any suitable natural product.

  这项发明提供了一种新颖、通用且简便的策略，用于创造具有高结构和立体化学复杂性的小分子。该方法的方面包括系统地应用于快速将易得的天然产物转化为具有多样分子结构的结构复杂化合物的环系统失真反应。通过评估化学性质，包括sp3碳的分数、ClogP和立体中心的数量，这些化合物被证明比标准筛选集合中的化合物显着更复杂和多样化。这种方法是通过来自三个不同结构类别的天然产物（赤霉酸、肾上腺酮和奎宁）来展示的，并描述了将该策略应用于任何合适的天然产物的方法。