(1R,5S,6R,7R)-3,3-ethylenedioxy-7-benzoyloxy-6-formylbicyclo[3,3,0]octane | 74818-14-7

• 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-formylbicyclo[3,3,0]octane
• 英文别名: (lR,5S,6R,7R)-3,3-ethylenedioxy-7-benzoyloxy-6formylbicyclo [3.3.0]octane；[(1'R,2'R,3'aR,6'aS)-1'-formylspiro[1,3-dioxolane-2,5'-2,3,3a,4,6,6a-hexahydro-1H-pentalene]-2'-yl] benzoate
• CAS: 74818-14-7
• 化学式: C₁₈H₂₀O₅
• 分子量: 316.354
• InChiKey: YNQURMQZAANBTO-QKPAOTATSA-N

物化性质

• 沸点：
  458.1±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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)-(3S,4RS)-3-hydroxy-4-methylnon-1-en-7-ynyl]-bicyclo[3,3,0]octane
  参考文献：
  名称：

  Carbacyclins, their preparation and use

  摘要：

  公式I中的Carbacyclin衍生物 ##STR1## 其中R.sub.1是OR.sub.2，其中R.sub.2是氢，烷基，环烷基，芳基，杂环残基或NHR.sub.3，其中R.sub.3是酸残基或氢；X是氧；A是--CH.sub.2 --CH.sub.2 --，trans--CH.dbd.CH--或--C.tbd.C--；W是自由或功能修饰的羟甲基或自由或功能修饰的 ##STR2## 其中OH基可以在.alpha.-或.beta.-位置；D是1-10碳原子的直链或支链，饱和或不饱和的脂肪族基，可以选择性地被氟原子，1,2-亚甲基，1,1-三甲基基取代；E是--C.tbd.C--或--CR.sub.6 .dbd.CR.sub.7 --，其中R.sub.6和R.sub.7是1-5碳原子的氢或烷基；R.sub.4是脂肪族基，环烷基，可选择性取代的芳基或杂环基；R.sub.5是自由或功能修饰的羟基，当R.sub.2是氢时，与碱的生理相容盐具有有价值的药理特性。

  公开号：

  US04423067A1

文献信息

• Carbacyclins, process for the preparation thereof, and use thereof as
  申请人：Schering Aktiengesellschaft

  公开号：US05124343A1

  公开（公告）日：1992-06-23

  The invention relates to carbacyclins of general Formula I ##STR1## wherein R.sub.1 is the residue CH.sub.2 OH or ##STR2## with R.sub.2 meaning a hydrogen atom, an alkyl, cycloalkyl, aryl residue, a ##STR3## or heterocyclic residue, or R.sub.1 is the residue ##STR4## with R.sub.3 meaning an alkanoyl or alkanesulfonyl residue of respectively 1-10 carbon atoms or the residue R.sub.2, or R.sub.1 is the residue ##STR5## wherein m is the number 1 or 2, X is an oxygen atom or a CH.sub.2 -group, A is a trans--CH.dbd.CH- or --.tbd.C--group, W is a free or functionally modified hydroxymethylene group wherein the OH-group can be in the .alpha.- or .beta.- position, n is the number 1, 2, or 3, D is a straight-chain alkylene group of 1-5 carbon atoms, E is a --C.tbd.C---bond or a --CR.sub.6 =CR.sub.7 --group wherein R.sub.6 and R.sub.7 are different from each other and mean a hydrogen atom or an alkyl group of 1-5 carbon atoms or a hydrogen atom or a halogen atom, preferably chlorine, R.sub.4 is an alkyl, cycloalkyl, or optionally substituted arly group, or a heterocyclic group, R.sub.5 is a free or functionally modified hydroxy group, and if R.sub.2 means a hydrogen atom, the salts thereof with physiologically compatible bases; to processes for the preparation thereof, and to the use thereof as blood-pressure-lowering agents.

  本发明涉及一般式I的碳环素，其中R1是残基CH2OH或 ##STR2## R2表示氢原子，烷基，环烷基，芳基残基， ##STR3## 或杂环残基，或R1是残基 ##STR4## 其中R3分别为1-10个碳原子的脂肪酰基或烷基磺酰基残基或残基R2，或R1是残基 ##STR5## 其中m是数字1或2，X是氧原子或CH2-基团，A是反式-CH=CH-或-.tbd.C-基团，W是自由或功能修饰的羟甲基基团，其中OH基团可以处于.alpha.-或.beta.-位置，n是数字1,2或3，D是1-5个碳原子的直链烷基基团，E是--C.tbd.C---键或--CR6=CR7--基团，其中R6和R7不同且表示1-5个碳原子的氢原子或烷基基团或氢原子或卤原子，优选为氯，R4是烷基，环烷基或可选取代的芳基基团或杂环基团，R5是自由或功能修饰的羟基团，如果R2表示氢原子，则与生理兼容的碱盐，其制备过程以及作为降低血压药物的用途。
• 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。
• 3-oxa-5-fluoro-carbacyclins, their preparation and use as medicinal
  申请人：Schering Aktiengesellschaft

  公开号：US05157042A1

  公开（公告）日：1992-10-20

  Carbacyclin derivatives of Formula I ##STR1## wherein R.sub.1 is OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, ##STR2## or a heterocyclic residue; or R.sub.1 is NHR.sub.3 wherein R.sub.3 is an acid residue (acyl) or R.sub.2 ; A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C--; W is a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR3## wherein the OH-group can be in the .alpha.- or .beta.-position; D is ##STR4## a straight-chain, saturated aliphatic group of 1-10 carbon atoms; or a branched, saturated or straight-chain or branched, unsaturated aliphatic group of 2-10 carbon atoms; all of which are substituted by fluorine atoms; n is 1, 2, or 3; E is a direct bond, --C.tbd.C--, or --CR.sub.6 .dbd.CR.sub.7 --, wherein R.sub.6 is hydrogen or alkyl of 1-5 carbon atoms and R.sub.7 is hydrogen, halogen or alkyl of 1-5 carbon atoms; R.sub.4 is an aliphatic group, cycloalkyl, optionally substituted aryl, or a heterocyclic group; and R.sub.5 is a free or functionally modified hydroxy group; and when R.sub.1 is OH, the salts thereof with physiologically compatible bases, are valuable pharmacological agents.

  公式I的Carbacyclin衍生物 ##STR1## 其中R.sub.1为OR.sub.2，其中R.sub.2为氢，烷基，环烷基，芳基， ##STR2## 或杂环残基; 或R.sub.1为NHR.sub.3，其中R.sub.3为酸残基（酰基）或R.sub.2; A为--CH.sub.2--CH.sub.2--，trans--CH.dbd.CH--，或--C.tbd.C--; W为自由或功能修饰的羟甲基烷基或自由或功能修饰的 ##STR3## 其中OH基可以在.alpha.-或.beta.-位置; D为 ##STR4## 1-10个碳原子的直链饱和脂肪基; 或2-10个碳原子的分支、饱和或直链或分支、不饱和的脂肪基; 所有这些基都被氟原子取代; n为1、2或3; E为直接键，--C.tbd.C--或--CR.sub.6.dbd.CR.sub.7--，其中R.sub.6为1-5个碳原子的氢或烷基，R.sub.7为氢、卤素或1-5个碳原子的烷基; R.sub.4为脂肪基，环烷基，可选取代芳基或杂环基; R.sub.5为自由或功能修饰的羟基; 当R.sub.1为OH时，与生理相容的碱盐是有价值的药理剂。
• 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。
• Novel carbacyclins, processes for their preparation and their use as
  申请人：Schering Aktiengesellschaft

  公开号：US05013758A1

  公开（公告）日：1991-05-07

  (5E)-13,14,18,18,19,19-hexadehydro-3-oxa-6a-carbaprostaglandin I.sub.2 derivatives of Formula I ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 are hydrogen or alkyl of 1-5 carbon atoms, and R.sub.5 is an alkyl group of 1-5 carbon atoms, as well as the physiologically compatible salts thereof; have pharmacologically valuable activity.

  (5E)-13,14,18,18,19,19- 六脱氢-3-氧-6a-碳基前列腺素I.sub.2 衍生物，其化学式为I，其中R.sub.1、R.sub.2、R.sub.3、R.sub.4为氢或1-5个碳原子的烷基，R.sub.5为1-5个碳原子的烷基，以及其生理兼容的盐；具有药理学上有价值的活性。