2-[(8S,9S,13S,14S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]acetic acid | 845884-35-7

• 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: 2-[(8S,9S,13S,14S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]acetic acid
• CAS: 845884-35-7
• 化学式: C₂₀H₂₆O₂
• 分子量: 298.425
• InChiKey: ASWPMXLWKYCLHU-XSYGEPLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(8S,9S,13S,14S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]acetic acid 在 lead(II) chloride RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 四甲基乙二胺 、 四氯化钛 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  RCM-Based Synthesis of a Variety of β-C-Glycosides and Their in Vitro Anti-Solid Tumor Activity

  摘要：

  The synthesis of a number of biologically relevant C-glycosides has been carried out through the use of an esterification-ring-closing metathesis (RCM) strategy. The required acid precursors were readily prepared via a number of standard chemical transformations followed by dehydrative coupling of these acids with several olefin alcohols 1 to yield the precursor esters 3 in excellent yield. Methylenation of the esters 3 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected beta-C-glycosides 6 in good overall yield. Several examples were converted to the corresponding C-glycoglycerolipids 17 and subsequently screened against solid-tumor cell lines for in vitro differential cytotoxicity.

  DOI：

  10.1021/jo040254t
• 作为产物：
  描述：

  17-去氧基雌二醇 在 lithium chloride 4-二甲氨基吡啶 、 sodium chlorite 、 potassium dihydrogenphosphate 、 9-borabicyclo[3.3.1]nonane dimer 、 四(三苯基膦)钯 、 2-甲基-2-丁烯 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 28.5h， 生成 2-[(8S,9S,13S,14S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]acetic acid
  参考文献：
  名称：

  RCM-Based Synthesis of a Variety of β-C-Glycosides and Their in Vitro Anti-Solid Tumor Activity

  摘要：

  The synthesis of a number of biologically relevant C-glycosides has been carried out through the use of an esterification-ring-closing metathesis (RCM) strategy. The required acid precursors were readily prepared via a number of standard chemical transformations followed by dehydrative coupling of these acids with several olefin alcohols 1 to yield the precursor esters 3 in excellent yield. Methylenation of the esters 3 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected beta-C-glycosides 6 in good overall yield. Several examples were converted to the corresponding C-glycoglycerolipids 17 and subsequently screened against solid-tumor cell lines for in vitro differential cytotoxicity.

  DOI：

  10.1021/jo040254t

文献信息

• Synthesis of Some Biologically Relevant β-<i>C</i>-Glycoconjugates
  作者：Maarten H. D. Postema、Jared L. Piper

  DOI：10.1021/ol034363q

  日期：2003.5.1

  [GRAPHICS]An esterification-RCM approach to a variety of biologically relevant beta-C-glycoconjugates is reported herein. A range of carboxylic acids were coupled with several different olefin alcohols 1 to provide esters 3. The esters were then converted to the final ring-closed product 6 in three steps in 49-60% overall yield. The formed compounds are biologically relevant and serve as stable carbohydrate mimics of the corresponding O-glycosides.
• [EN] AROMATIC STEROID 5-(ALPHA)-REDUCTASE INHIBITORS
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：WO1989011282A1

  公开（公告）日：1989-11-30

  (EN) Invented are substituted acrylate analogues of steroidal synthetic compounds, pharmaceutical compositions containing the compounds, and methods of using these compounds to inhibit steroid 5-$g(a)-reductase including using these compounds to reduce prostate size. Also invented are intermediates used in preparing these compounds.(FR) Analogues d'acrylates substitués de composés stéroïdes synthétiques, préparations pharmaceutiques contenant ces composés et procédés d'utilisation de ces composés pour inhiber la 5-$g(a)-réductase stéroïde, y compris pour réduire la taille de la prostate. On a également découvert des produits intermédiaires utilisés dans la production desdits composés.
• RCM-Based Synthesis of a Variety of β-<i>C</i>-Glycosides and Their in Vitro Anti-Solid Tumor Activity
  作者：Maarten H. D. Postema、Jared L. Piper、Russell L. Betts、Frederick A. Valeriote、Halina Pietraszkewicz

  DOI：10.1021/jo040254t

  日期：2005.2.1

  The synthesis of a number of biologically relevant C-glycosides has been carried out through the use of an esterification-ring-closing metathesis (RCM) strategy. The required acid precursors were readily prepared via a number of standard chemical transformations followed by dehydrative coupling of these acids with several olefin alcohols 1 to yield the precursor esters 3 in excellent yield. Methylenation of the esters 3 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected beta-C-glycosides 6 in good overall yield. Several examples were converted to the corresponding C-glycoglycerolipids 17 and subsequently screened against solid-tumor cell lines for in vitro differential cytotoxicity.