3α,5α-dihydroxy-2β-(benzyloxymethyl)cyclopentane-1α-acetic acid γ-lactone 3-tetrahydropyran-2-yl ether | 32233-38-8

• 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: 3α,5α-dihydroxy-2β-(benzyloxymethyl)cyclopentane-1α-acetic acid γ-lactone 3-tetrahydropyran-2-yl ether
• 英文别名: 3α,5α-dihydroxy-2β-benzyloxymethyl-1α-acetic acid γ-lactone 3-tetrahydropyranyl ether；(1S,5R,6S,7R)-6-Benzyloxymethyl-7-(tetrahydropyran-2-yloxy)-2-oxabicyclo[3,3,0]octan-3-one；(3aR,4S,5R,6aS)-5-(oxan-2-yloxy)-4-(phenylmethoxymethyl)-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
• CAS: 32233-38-8
• 化学式: C₂₀H₂₆O₅
• 分子量: 346.423
• InChiKey: LLFMCCBDEXWDDP-HPUPVJTASA-N

物化性质

• 沸点：
  509.6±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3α,5α-dihydroxy-2β-(benzyloxymethyl)cyclopentane-1α-acetic acid γ-lactone 3-tetrahydropyran-2-yl ether 在 sodium hydroxide 、 正丁基锂 、 二氯氧化铬 、 二异丙胺 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 6.42h， 生成 methyl 2-((4S,5R)-4-((benzyloxy)methyl)-2-oxo-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-6aH-cyclopenta[b]furan-6a-yl)-2-(trimethylsilyl)acetate
  参考文献：
  名称：

  轻松合成6a-carbaprostaglandin i 2

  摘要：

  由天然前列腺素的一般合成中间体内酯4或羟酸5合成了光学活性的6a-carbaprostaglandin I 2（2），它是天然前列腺素（1）的稳定模拟物。

  DOI：

  10.1016/0040-4020(81)80005-1
• 作为产物：
  描述：

  (3aR,4S,5S,6R,6aR)-6-iodo-5-(oxan-2-yloxy)-4-(phenylmethoxymethyl)-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 生成 3α,5α-dihydroxy-2β-(benzyloxymethyl)cyclopentane-1α-acetic acid γ-lactone 3-tetrahydropyran-2-yl ether
  参考文献：
  名称：

  通过高度立体选择性不对称狄尔斯-阿尔德反应合成核内酯

  摘要：

  我们已经成功地在衍生自市售D-泛内酯的手性丙烯酸酯与5-苄氧基甲基-环戊二烯之间进行了高度立体选择性的不对称Diels-Alder反应，从而以94％的de和79％的产率获得了用于合成Corey内酯的加合物。

  DOI：

  10.1016/0040-4039(91)80038-8

文献信息

• Facile synthesis of 6a-carbaprostaglandin i2
  作者：Yoshitaka Konishi、Masanori Kawamura、Yoichi Iguchi、Yoshinobu Arai、Masaki Hayashi

  DOI：10.1016/0040-4020(81)80005-1

  日期：1981.1

  The optically active 6a-carbaprostaglandin I2 (2), a stable mimic of natural prostacylin (1), was synthesized from the lactone 4 or the hydroxy acid 5, which were general synthetic intermediates for natural prostaglandins.

  由天然前列腺素的一般合成中间体内酯4或羟酸5合成了光学活性的6a-carbaprostaglandin I 2（2），它是天然前列腺素（1）的稳定模拟物。
• A New Carbacyclin Synthesis
  作者：Bärbel Bennua、Helmut Dahl、Helmut Vorbrüggen

  DOI：10.1055/s-1986-31469

  日期：——

  After opening of substituted Corey lactones by alkali, acidification and Jones oxidation to the γ-keto acids, reaction with triphenyl-(phenyliminovinylidene)-phosphorane afforded in 50% overall yield the corresponding unsaturated bicyclo[3.3.0]octane-1-one derivatives, which could be readily reduced to the saturated bicyclic ketones.

  在碱、酸和琼斯氧化作用下，被取代的科里内酯被打开，生成γ-酮酸，与三苯基（苯亚氨基乙烯基）膦反应，总产率为50%，得到相应的不饱和双环[3.3.0]辛烷-1-酮衍生物，这些衍生物可以很容易地还原为饱和双环酮。
• 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.

  此化合物的公式为 ##STR1## 其中R.sub.1为(a)氢，(b)C.sub.1-10烷基，(c)C.sub.1-10被卤素取代的烷基; C.sub.1-4烷氧基; C.sub.6-10芳基; C.sub.6-10被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烷氧基取代的芳基; 二C.sub.1-4-烷基胺基; 或三C.sub.1-4-烷基铵，(d)C.sub.4-10环烷基，(e)C.sub.4-10被C.sub.1-4烷基取代的环烷基，(f)C.sub.6-10芳基，(g)C.sub.6-10被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烷氧基取代的芳基，或(h)5或6个环原子之一为O、N或S的芳香族杂环; A为--CH.sub.2--CH.sub.2--，trans--CH.dbd.CH--或--C.tbd.C--; W为羟甲基，RO-亚甲基，CH.sub.3或CH.sub.3，##STR2## 其中OH或OR在α-或β-位置，并且R是一种在体内可水解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在一起是直接键，或者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被氟取代，而E是氧，--C.tbd.C--或直接键; R.sub.2为(a)C.sub.1-10烃基，(b)C.sub.6-10被C.sub.6-10芳基或C.sub.6-10被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烷氧基取代的芳基;(c)C.sub.4-10环烷基，(d)C.sub.4-10被C.sub.1-4烷基取代的环烷基，(e)C.sub.6-10芳基，(f)C.sub.6-10被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烷氧基取代的芳基，或(h)5或6个环原子之一为O、N或S的芳香族杂环; R.sub.3为OH或OR; 当R.sub.1为氢时，与生理兼容的碱盐对高血压、支气管扩张剂、血小板聚集抑制剂等具有有效作用。
• Konishi, Yoshitaka; Kawamura, Masanori; Iguchi, Yoichi, Tetrahedron, 1981, vol. 37, # 25, p. 4391 - 4399
  作者：Konishi, Yoshitaka、Kawamura, Masanori、Iguchi, Yoichi、Arai, Yoshinobu、Hayashi, Masaki

  DOI：——

  日期：——
• US4692464A
  申请人：——

  公开号：US4692464A

  公开（公告）日：1987-09-08