(1'S,2'R,10'S,11'S,15'S,17'S)-2',15'-Dimethyl-17'-phenyldispiro[1,3-dioxolane-2,5'-tetracyclo[8.7.0.02,7.011,15]heptadecane-14',2''-[1,3]dioxolan]-7'-en-17'-ol | 366014-79-1

• 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: (1'S,2'R,10'S,11'S,15'S,17'S)-2',15'-Dimethyl-17'-phenyldispiro[1,3-dioxolane-2,5'-tetracyclo[8.7.0.02,7.011,15]heptadecane-14',2''-[1,3]dioxolan]-7'-en-17'-ol
• CAS: 366014-79-1
• 化学式: C₂₉H₃₈O₅
• 分子量: 466.618
• InChiKey: YATKMKYCBKTEJF-QFLXWJJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  34
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1'S,2'R,10'S,11'S,15'S,17'S)-2',15'-Dimethyl-17'-phenyldispiro[1,3-dioxolane-2,5'-tetracyclo[8.7.0.02,7.011,15]heptadecane-14',2''-[1,3]dioxolan]-7'-en-17'-ol 在 正丁基锂 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.58h， 生成 11α-phenyl-3,3:17,17-bis(ethylenedioxy)androst-5-ene
  参考文献：
  名称：

  多种受阻草酸酯用于立体选择性制备新型11修饰的Androst-5-ene衍生物

  摘要：

  使用高度受阻的11β-羟基雄烯基-5-烯的草酸酯衍生物可生产11α和11β改性的雄烯基5-烯衍生物3a，b以及环外和内环脱水化合物4a - c和5b - c。1a - c。通过在自由基条件下通过分子内5-exo环化由相应的草酸酯作为前体，首次以良好的非对映选择性生产11-四氢呋喃衍生物6。

  DOI：

  10.1021/jo0401016
• 作为产物：
  描述：

  肾上腺甾酮 在 对甲苯磺酸 作用下， 以 二丁醚 、 甲苯 为溶剂， 反应 8.0h， 生成 (1'S,2'R,10'S,11'S,15'S,17'S)-2',15'-Dimethyl-17'-phenyldispiro[1,3-dioxolane-2,5'-tetracyclo[8.7.0.02,7.011,15]heptadecane-14',2''-[1,3]dioxolan]-7'-en-17'-ol
  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

文献信息

• Improved addition of organolithium reagents to hindered and/or enolisable ketones
  作者：Vincent Lecomte、Elie Stéphan、Franck Le Bideau、Gérard Jaouen

  DOI：10.1016/s0040-4020(03)00189-3

  日期：2003.3

  the addition of some aryl- and alkyllithium derivatives to some hindered and/or enolisable ketones in different solvents (polar and apolar) and, in some cases, at different temperatures and reaction times, will be presented here. The reversibility of the addition of aryllithium to these specific ketones will be observed and discussed. This approach is then used to prepare new steroids as precursor for

  本文将介绍在不同溶剂（极性和非极性）中，在某些情况下，在不同的温度和反应时间下，将某些芳基和烷基锂衍生物添加到某些受阻和/或可烯化的酮中的研究。将观察和讨论向这些特定的酮中添加芳基锂的可逆性。然后，该方法用于制备新的类固醇作为潜在有趣的取代睾丸激素的前体。
• A ring-distortion strategy to construct stereochemically complex and structurally diverse compounds from natural products
  作者：Robert W. Huigens III、Karen C. Morrison、Robert W. Hicklin、Timothy A. Flood Jr、Michelle F. Richter、Paul J. Hergenrother

  DOI：10.1038/nchem.1549

  日期：2013.3

  High-throughput screening is the dominant method used to identify lead compounds in drug discovery. As such, the makeup of screening libraries largely dictates the biological targets that can be modulated and the therapeutics that can be developed. Unfortunately, most compound-screening collections consist principally of planar molecules with little structural or stereochemical complexity, compounds that do not offer the arrangement of chemical functionality necessary for the modulation of many drug targets. Here we describe a novel, general and facile strategy for the creation of diverse compounds with high structural and stereochemical complexity using readily available natural products as synthetic starting points. We show through the evaluation of chemical properties (which include fraction of sp3 carbons, ClogP and the number of stereogenic centres) that these compounds are significantly more complex and diverse than those in standard screening collections, and we give guidelines for the application of this strategy to any suitable natural product. An approach for the construction of complex and diverse compound libraries is described, whereby natural products are altered through a series of ring system distortion reactions. The compounds produced have markedly different physiochemical properties from those in standard screening collections and thus could offer advantages in the search for lead molecules that can be developed into drug candidates.

  高通量筛选是药物发现过程中确定先导化合物的主要方法。因此，筛选库的组成在很大程度上决定了可调节的生物靶点和可开发的治疗方法。遗憾的是，大多数化合物筛选库主要由结构或立体化学复杂性较低的平面分子组成，这些化合物无法提供调节许多药物靶点所需的化学功能排列。在这里，我们介绍了一种新颖、通用和简便的策略，即利用现成的天然产物作为合成起点，创造出具有高结构和立体化学复杂性的多种化合物。我们通过对化学性质（包括 sp3 碳的比例、ClogP 和立体中心的数量）的评估表明，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。本文介绍了一种构建复杂多样化合物库的方法，即通过一系列环系统畸变反应改变天然产物。生成的化合物与标准筛选库中的化合物具有明显不同的理化性质，因此在寻找可开发成候选药物的先导分子方面具有优势。
• 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。
• Addition of aryllithiums to an 11-oxo-steroid
  作者：Vincent Lecomte、Nicolas Foy、Franck Le Bideau、Elie Stéphan、Gérard Jaouen

  DOI：10.1016/s0040-4039(01)01033-4

  日期：2001.8

  The addition of aryllithiums to an 11-oxo-steroid is possible in non-polar medium and at room temperature. A series of protected 11 alpha -aryl-11 beta -hydroxy-androsten-diones have been prepared. (C) 2001 Elsevier Science Ltd. All rights reserved.
• [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.