5-ethenyl-3-(hydroxymethylene)-4,4a,7,8-tetrahydro-4a-methyl-2(3H)-naphthalenone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-ethenyl-3-(hydroxymethylene)-4,4a,7,8-tetrahydro-4a-methyl-2(3H)-naphthalenone
• 英文别名: (3Z)-5-ethenyl-3-(hydroxymethylidene)-4a-methyl-7,8-dihydro-4H-naphthalen-2-one
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: DYRCZMWPDOABLI-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  5-ethenyl-3-(hydroxymethylene)-4,4a,7,8-tetrahydro-4a-methyl-2(3H)-naphthalenone 在 sodium acetate 、 sodium hydride 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 26.0h， 生成 8-(4-fluorophenyl)-4a,5,6,8,11,11a-hexahydro-11a,1',3'-trimethylspiro<<1>-benzopyrano<5,6-f>indazole-3(2H),5'(2'H)-pyrimidine>-2',4',6'(1'H,3'H)-trione
  参考文献：
  名称：

  Non-steroidal glucocorticoid-like substances: receptor binding and in vivo activity

  摘要：

  Compounds of general structure I, prepared by a Diels-Alder reaction with diene 3, are relatives of the known potent glucocorticoid II but possess a markedly modified C- and D-ring environment. Despite these structural changes, 4, 5, 9, 10, 12a, 13, and 14 bound to the glucocorticoid receptor with an affinity which approximated that of the reference standard, 6-alpha-methylprednisolone. Four of these compounds not only exhibited antiinflammatory activity in the alpha-tocopherol pouch test but also exhibited marked adrenal suppression and other typical glucocorticoid properties at doses in the same range as the effective antiinflammatory doses.

  DOI：

  10.1021/jm00074a008
• 作为产物：
  描述：

  甲酸甲酯 、 5-ethenyl-4,4a,7,8-tetrahydro-4a-methyl-2(3H)-naphthalenone 在 盐酸 、 sodium methylate 作用下， 以 四氢呋喃 、 ice-water 为溶剂， 生成 5-ethenyl-3-(hydroxymethylene)-4,4a,7,8-tetrahydro-4a-methyl-2(3H)-naphthalenone
  参考文献：
  名称：

  1-Ethenyl-6-(4-ph

  摘要：

  新型化合物，1-烯基-6-(4-R'-苯基)-3,4,9,9a-四氢-9a-甲基-6H-萘并[2,3-c]吡唑，其中R'为氢或氟，可用作制备抗炎药物的中间体。

  公开号：

  US04452988A1

文献信息

• Anti-inflammatory 8H-phenanthro-[2,3-c]pyrazole derivatives
  申请人：Sterling Drug Inc.

  公开号：US04349558A1

  公开（公告）日：1982-09-14

  The compounds of the formulas ##STR1## where R and R' are lower-alkyl possess glucocorticoid activity, and are prepared by reacting the compound of the formula ##STR2## with the appropriate dienophile.

  公式为##STR1##的化合物，其中R和R'是低烷基，具有糖皮质激素活性，并通过将公式为##STR2##的化合物与适当的二烯亲电体反应制备而成。
• Pentacyclic phenylpyrazole compounds as anti-inflammatory agents
  申请人：Sterling Drug Inc.

  公开号：US04412995A1

  公开（公告）日：1983-11-01

  Compounds of the formula ##STR1## where R is hydrogen, methyl, ethyl, propyl, 2-propenyl or 2-propynyl; and R' is hydrogen or fluoro possess anti-inflammatory activity. The compounds where R is H are prepared by reacting a compound of the formula ##STR2## with (1H,3H)-pyrimidine-2,4,5,6-tetrone. The compounds where R is other than hydrogen are prepared by reacting a compound where R is hydrogen with the appropriate alkylating agent.

  式为##STR1##的化合物，其中R为氢、甲基、乙基、丙基、2-丙烯基或2-丙炔基；R'为氢或氟的具有抗炎活性。其中R为H的化合物通过将式为##STR2##的化合物与(1H,3H)-嘧啶-2,4,5,6-四酮反应制备。而R不是氢的化合物则通过将R为氢的化合物与适当的烷基化剂反应制备。
• 1-Ethenyl-6-(4-ph
  申请人：Sterling Drug Inc.

  公开号：US04452988A1

  公开（公告）日：1984-06-05

  Novel compounds, 1-ethenyl-6-(4-R'-phenyl)-3,4,9,9a-tetrahydro-9a-methyl-6H-naphtho[2,3-c]p yrazoles, wherein R' is hydrogen or fluoro, are useful as intermediates in the preparation of anti-inflammatory agents.

  新型化合物，1-烯基-6-(4-R'-苯基)-3,4,9,9a-四氢-9a-甲基-6H-萘并[2,3-c]吡唑，其中R'为氢或氟，可用作制备抗炎药物的中间体。
• Phenanthro[2,3-c]pyrazole
  申请人：Sterling Drug Inc.

  公开号：US04307102A1

  公开（公告）日：1981-12-22

  The compound of the formula ##STR1## possesses glucocorticoid activity, and is prepared by reacting the compound of the formula ##STR2## with 2-vinylpyridine.

  这个化学式##STR1##的化合物具有糖皮质激素活性，并通过将化学式##STR2##的化合物与2-乙烯基吡啶反应制备而成。
• Anti-inflammatory
  申请人：Sterling Drug Inc.

  公开号：US04349559A1

  公开（公告）日：1982-09-14

  The compounds of formula ##STR1## where R is hydrogen or fluorine possess glucocorticoid activity, and are prepared by reacting a compound of the formula ##STR2## with 1,2,3-indantrione.

  式##STR1##中的化合物，其中R是氢或氟，具有糖皮质激素活性，并通过将式##STR2##的化合物与1,2,3-茚酮反应制备而成。