(1R,5S,6R,7R)-3,3-Ethylenedioxy-7-benzoyloxy-6-[(E)-3-oxo-4-phenyl-1-butenyl]bicyclo[3,3,0]octane | 74818-21-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,5S,6R,7R)-3,3-Ethylenedioxy-7-benzoyloxy-6-[(E)-3-oxo-4-phenyl-1-butenyl]bicyclo[3,3,0]octane
• 英文别名: (1R,5S,6R,7R)-3,3-Ethylenedioxy-7-benzoyloxy-6-[(E)-3-oxo-4-phenyl-1-butenyl]bicyclo[3,3,0]octan；[(1'R,2'R,3'aR,6'aS)-1'-[(E)-3-oxo-4-phenylbut-1-enyl]spiro[1,3-dioxolane-2,5'-2,3,3a,4,6,6a-hexahydro-1H-pentalene]-2'-yl] benzoate
• CAS: 74818-21-6
• 化学式: C₂₇H₂₈O₅
• 分子量: 432.516
• InChiKey: HWNFAPBKOSDMJL-YDEBXIOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1R,5S,6R,7R)-3,3-ethylenedioxy-7-benzoyloxy-6-formylbicyclo[3,3,0]octane 生成 (1R,5S,6R,7R)-3,3-Ethylenedioxy-7-benzoyloxy-6-[(E)-3-oxo-4-phenyl-1-butenyl]bicyclo[3,3,0]octane
  参考文献：
  名称：

  Process for the production of caracyclin intermediates

  摘要：

  一种制备式为##STR1##的3-氧代-7-羟基-双环[3,3,0]辛烷-2-基羧酸酯的方法，其中R.sub.1是1-6碳原子的烷基或7-10碳原子的苯基烷基，R.sub.2是氢、1-6碳原子的烷基或苯基烷基、四氢吡喃基、四氢呋喃基、α-乙氧基乙基、三个C.sub.1-4-烷基硅基，其中烷基部分可以选择性地被苯基取代，或式##STR2##其中R.sub.3是1-6碳原子的烷基或6-12碳原子的芳基，包括将对应的式为##STR3##的7-羟基-2-氧代双环[3,3,0]辛烷-3-基乙烯基乙酸酯（其中R.sub.1和R.sub.2如上所定义）氧化成相应的酮，将后者与打开含有醚氧基的环的碱基反应，然后还原所得产物以制备3-氧代-7-羟基-双环[3,3,0]辛烷-2-基羧酸酯。

  公开号：

  US04359581A1

文献信息

• Process for the production of caracyclin intermediates
  申请人：Schering AG

  公开号：US04359581A1

  公开（公告）日：1982-11-16

  A process for preparing a 3-oxo-7-hydroxy-bicyclo[3,3,0]octan-2-ylcarboxylic acid ester of the formula ##STR1## wherein R.sub.1 is alkyl of 1-6 carbon atoms or phenalkyl of 7-10 carbon atoms and R.sub.2 is hydrogen, alkyl or 1-6 carbon atoms, phenalkyl of 7-10 carbon atoms, tetrahydropyranyl, tetrahydrofuranyl, .alpha.-ethoxyethyl, tri-C.sub.1-4 -alkylsilyl, wherein the alkyl moieties can optionally be substituted by phenyl, or ##STR2## wherein R.sub.3 is alkyl of 1-6 carbon atoms or aryl of 6-12 carbon atoms, comprises oxidizing the corresponding 7-hydroxy-2-oxabicyclo [3,3,0]octan-3-ylideneacetic acid ester of the formula ##STR3## wherein R.sub.1 and R.sub.2 are as defined above, to form the corresponding ketone, reacting the latter with a base which opens the ether oxygen containing ring, and then reducing the resultant product to prepare the 3-oxo-7-hydroxy-bicyclo[3,3,0]octan-2-ylcarboxylic acid ester.

  一种制备式为##STR1##的3-氧代-7-羟基-双环[3,3,0]辛烷-2-基羧酸酯的方法，其中R.sub.1是1-6碳原子的烷基或7-10碳原子的苯基烷基，R.sub.2是氢、1-6碳原子的烷基或苯基烷基、四氢吡喃基、四氢呋喃基、α-乙氧基乙基、三个C.sub.1-4-烷基硅基，其中烷基部分可以选择性地被苯基取代，或式##STR2##其中R.sub.3是1-6碳原子的烷基或6-12碳原子的芳基，包括将对应的式为##STR3##的7-羟基-2-氧代双环[3,3,0]辛烷-3-基乙烯基乙酸酯（其中R.sub.1和R.sub.2如上所定义）氧化成相应的酮，将后者与打开含有醚氧基的环的碱基反应，然后还原所得产物以制备3-氧代-7-羟基-双环[3,3,0]辛烷-2-基羧酸酯。
• US4359581A
  申请人：——

  公开号：US4359581A

  公开（公告）日：1982-11-16
• US4692464A
  申请人：——

  公开号：US4692464A

  公开（公告）日：1987-09-08
• Novel prostacyclin derivatives and a process for the preparation thereof
  申请人：Schering Aktiengesellschaft

  公开号：US04692464A1

  公开（公告）日：1987-09-08

  Compounds of the formula ##STR1## wherein R.sub.1 is (a) hydrogen, (b) C.sub.1-10 alkyl, (c) C.sub.1-10 alkyl substituted by halogen; C.sub.1-4 alkoxy; C.sub.6-10 aryl; C.sub.6-10 aryl substituted by 1-3 halogen atoms, a phenyl group, 1-3 C.sub.1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C.sub.1-4 alkoxy group; di-C.sub.1-4 -alkylamino; or tri-C.sub.1-4 -alkylammonium, (d) C.sub.4-10 cycloalkyl, (e) C.sub.4-10 cycloalkyl substituted by C.sub.1-4 alkyl, (f) C.sub.6-10 aryl, (g) C.sub.6-10 aryl substituted by 1-3 halogen atoms, a phenyl group 1-3 C.sub.1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C.sub.1-4 alkoxy group, or (h) an aromatic heterocycle of 5 or 6 ring atoms one of which is O, N or S; A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C--; W is hydroxymethylene, RO-methylene, CH.sub.3 or CH.sub.3, ##STR2## wherein OH or OR is in the .alpha.- or .beta.-position and R is an in vivo hydrolyzable and physiologically acceptable ether or acyl group which is conventional for modifying OH groups in prostaglandins; D and E together are a direct bond, or D is C.sub.1-10 alkylene, C.sub.1-10 alkenylene or C.sub.1-10 alkynylene or one of these groups substituted by fluorine, and E is oxygen, --C.tbd.C-- or a direct bond; R.sub.2 is (a) a C.sub.1-10 hydrocarbon aliphatic radical, (b) a C.sub.6-10 hydrocarbon aliphatic radical substituted by C.sub.6-10 aryl or by C.sub.6-10 aryl substituted by 1-3 halogen atoms, a phenyl group, 1-3 C.sub.1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C.sub.1-4 alkoxy group; (c) C.sub.4-10 cycloalkyl, (d) C.sub.4-10 cycloalkyl substituted by C.sub.1-4 alkyl, (e) C.sub.6-10 aryl, (f) C.sub.6-10 aryl substituted by 1-3 halogen atoms, a phenyl group, 1-3 C.sub.1-4 alkyl groups or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, hydroxy or C.sub.1-4 alkoxy group; or (h) an aromatic heterocycle of 5 or 6 ring atoms one of which is O, N or S; and R.sub.3 is OH or OR; and, when R.sub.1 is hydrogen, the salts thereof with physiologically compatible bases, are effective as antihypertensive, bronchiodilators, thrombocyte aggregation inhibitors, inter alia.

  化合物的公式为##STR1##其中R.sub.1是(a)氢，(b)C.sub.1-10烷基，(c)C.sub.1-10卤代烷基;C.sub.1-4烷氧基;C.sub.6-10芳基;C.sub.6-10芳基取代1-3个卤素原子、苯基、1-3个C.sub.1-4烷基或氯甲基、氟甲基、三氟甲基、羧基、羟基或C.sub.1-4烷氧基;二C.sub.1-4-烷基氨基;或三C.sub.1-4-烷基铵盐，(d)C.sub.4-10环烷基，(e)C.sub.4-10环烷基取代C.sub.1-4烷基，(f)C.sub.6-10芳基，(g)C.sub.6-10芳基取代1-3个卤素原子、苯基、1-3个C.sub.1-4烷基或氯甲基、氟甲基、三氟甲基、羧基、羟基或C.sub.1-4烷氧基，或(h)5或6个环原子的芳香杂环中的一个是O、N或S;A是--CH.sub.2--CH.sub.2--、反-CH.dbd.CH--或--C.tbd.C--;W是羟甲基、RO-甲基、CH.sub.3或CH.sub.3, ##STR2##其中OH或OR在.alpha.-或.beta.-位置，R是体内水解的并且生理上可接受的醚或酰基，用于修饰前列腺素中的OH基团;D和E一起是直接键，或D是C.sub.1-10烷基、C.sub.1-10烯基或C.sub.1-10炔基或这些基团之一取代氟，E是氧、--C.tbd.C--或直接键;R.sub.2是(a)C.sub.1-10碳氢化合物脂肪基，(b)C.sub.6-10碳氢化合物脂肪基取代C.sub.6-10芳基或C.sub.6-10芳基取代1-3个卤素原子、苯基、1-3个C.sub.1-4烷基或氯甲基、氟甲基、三氟甲基、羧基、羟基或C.sub.1-4烷氧基;(c)C.sub.4-10环烷基，(d)C.sub.4-10环烷基取代C.sub.1-4烷基，(e)C.sub.6-10芳基，(f)C.sub.6-10芳基取代1-3个卤素原子、苯基、1-3个C.sub.1-4烷基或氯甲基、氟甲基、三氟甲基、羧基、羟基或C.sub.1-4烷氧基;或(h)5或6个环原子的芳香杂环中的一个是O、N或S;R.sub.3是OH或OR;当R.sub.1为氢时，与生理兼容的碱盐是抗高血压、支气管扩张剂、血小板聚集抑制剂等的有效药物。