3a-methyl-6-(3-oxo-butyl)-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione | 924881-85-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3a-methyl-6-(3-oxo-butyl)-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione
• 英文别名: (3aR,4S,7aS)-3a-methyl-6-(3-oxobutyl)-1,2,4,5,9a,9b-hexahydro-3aH-9-oxacyclopenta[a]naphthalene-3,7-dione；(6aS,9aR,9bS)-6a-methyl-4-(3-oxobutyl)-5,6,8,9,9a,9b-hexahydrocyclopenta[h]chromene-3,7-dione
• CAS: 924881-85-6
• 化学式: C₁₇H₂₂O₄
• 分子量: 290.359
• InChiKey: UFHNRPGLRDOLMF-XKQJLSEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3a-methyl-6-(3-oxo-butyl)-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 6.5h， 生成 (8S,13S,14R,17S)-17-acetoxy-7-oxo-estra-4,9-diene-3-one
  参考文献：
  名称：

  Enantioselective synthesis of (8S,13S,14R)-7-oxa-estra-4,9-diene-3,17-dione

  摘要：

  The first enantioselective synthesis of (8S,13S,14R)-7-oxa-estra-4,9-diene-3,17-dione with the trans-C/D ring junction is described. Key features of the synthesis include Ag2O-mediated C-O bond formation, thermodynamically controlled axial-equatorial inversion, one-pot of halogen exchange and Co/Cr-mediated C-C bond formation, and intramolecular aldol condensations. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.042
• 作为产物：
  描述：

  5-氯-2-戊酮 在 盐酸 、 sodium methylate 、 戴斯-马丁氧化剂 、 potassium iodide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 38.0h， 生成 3a-methyl-6-(3-oxo-butyl)-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione
  参考文献：
  名称：

  Enantioselective synthesis of (8S,13S,14R)-7-oxa-estra-4,9-diene-3,17-dione

  摘要：

  The first enantioselective synthesis of (8S,13S,14R)-7-oxa-estra-4,9-diene-3,17-dione with the trans-C/D ring junction is described. Key features of the synthesis include Ag2O-mediated C-O bond formation, thermodynamically controlled axial-equatorial inversion, one-pot of halogen exchange and Co/Cr-mediated C-C bond formation, and intramolecular aldol condensations. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.042

文献信息

• OXA-STEROIDS DERIVATIVES AS SELECTIVE PROGESTERONE RECEPTOR MODULATORS
  申请人：Kang Fu-An

  公开号：US20070197635A1

  公开（公告）日：2007-08-23

  The present invention is directed to novel 7-oxa-estra-4,9-diene-3,17-dione derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by at least one progesterone or glucocorticoid receptor.

  本发明涉及新颖的7-氧杂雌甾-4,9-二烯-3,17-二酮衍生物，含有它们的药物组合物以及它们在治疗至少受孕激素或糖皮质激素受体调节的疾病和症状中的应用。
• US7763648B2
  申请人：——

  公开号：US7763648B2

  公开（公告）日：2010-07-27
• Enantioselective synthesis of (8S,13S,14R)-7-oxa-estra-4,9-diene-3,17-dione
  作者：Fu-An Kang、Nareshkumar Jain、Zhihua Sui

  DOI：10.1016/j.tetlet.2006.11.042

  日期：2007.1

  The first enantioselective synthesis of (8S,13S,14R)-7-oxa-estra-4,9-diene-3,17-dione with the trans-C/D ring junction is described. Key features of the synthesis include Ag2O-mediated C-O bond formation, thermodynamically controlled axial-equatorial inversion, one-pot of halogen exchange and Co/Cr-mediated C-C bond formation, and intramolecular aldol condensations. (c) 2006 Elsevier Ltd. All rights reserved.