Δ²-trans-6-Keto-prostaglandin E1 methyl ester | 70666-27-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Δ²-trans-6-Keto-prostaglandin E1 methyl ester
• 英文别名: 6-Oxo-(E)-Δ²-PGE(1)-methylester；(2E,13E)-(11α,15S)-6,9-Dioxo-11,15-dihydroxyprosta-2,13-dienoic acid methyl ester；methyl (E)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]-6-oxohept-2-enoate
• CAS: 70666-27-2
• 化学式: C₂₁H₃₂O₆
• 分子量: 380.481
• InChiKey: RGJKKVFKQHHOSQ-SQAHVLIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Δ²-trans-6-Keto-prostaglandin E1 methyl ester 在 phosphate buffer 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以84%的产率得到Δ²-trans-6-Keto-prostaglandin E1
  参考文献：
  名称：

  Synthesis of the key component for preparation of 6-ketoprostaglandins by a two-component coupling process: synthesis of 6-keto-prostaglandin E₁, ornoprostil and Δ²-trans-6-ketoprostaglandin E₁

  摘要：

  Starting with commercially available (3S,4R)-3-(methoxymethyloxy)-2-methylidene-4- siloxycyclopentanone-2, useful 6-keto-prostaglandin intermediates 1 have been prepared in good yields by a sequence of reactions which includes treatment with NaBr in the presence of BF3 . OEt(2), Pd-catalysed coupling of the resulting 2-bromomethyl-4-siloxycyclopent-2-enone 3 with the alkenylborane 4 or 9 and conversion of the alkenyl moiety into an epoxy and then into a keto group. The synthesis of 6-keto-PGE(1), ornoprostil and Delta(2)-trans-6-keto-PGE(1) by using 1 is also described.

  DOI：

  10.1039/p19960000715
• 作为产物：
  描述：

  (1E,3S)-1-iodo-3-(tert-butyldimethylsiloxy)-1-octene 在 吡啶 、 2-thienyl(cyano)copper lithium 、 叔丁基锂 、 氟化氢吡啶 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 Δ²-trans-6-Keto-prostaglandin E1 methyl ester
  参考文献：
  名称：

  Synthesis of the key component for preparation of 6-ketoprostaglandins by a two-component coupling process: synthesis of 6-keto-prostaglandin E₁, ornoprostil and Δ²-trans-6-ketoprostaglandin E₁

  摘要：

  Starting with commercially available (3S,4R)-3-(methoxymethyloxy)-2-methylidene-4- siloxycyclopentanone-2, useful 6-keto-prostaglandin intermediates 1 have been prepared in good yields by a sequence of reactions which includes treatment with NaBr in the presence of BF3 . OEt(2), Pd-catalysed coupling of the resulting 2-bromomethyl-4-siloxycyclopent-2-enone 3 with the alkenylborane 4 or 9 and conversion of the alkenyl moiety into an epoxy and then into a keto group. The synthesis of 6-keto-PGE(1), ornoprostil and Delta(2)-trans-6-keto-PGE(1) by using 1 is also described.

  DOI：

  10.1039/p19960000715

文献信息

• Prostaglandin analogues
  申请人：Ono Pharmaceutical Co. Ltd.

  公开号：US04215142A1

  公开（公告）日：1980-07-29

  Prostaglandin E.sub.1 analogues of the general formula: ##STR1## [wherein Y represents ethylene or trans-vinylene, Z represents ethylene or trans-vinylene, R.sup.1 represents a hydrogen atom, an alkyl group containing from 1 to 12 carbon atoms, an aralkyl group containing from 7 to 12 carbon atoms, a cycloalkyl group containing from 4 to 7 carbon atoms and unsubstituted or substituted by at least one alkyl group containing from 1 to 6 carbon atoms, a phenyl group unsubstituted or substituted by at least one chlorine atom, trifluoromethyl group, alkyl group containing from 1 to 4 carbon atoms or phenyl group, a --C.sub.m H.sub.2m COOR.sup.5 group (wherein m represents an integer of from 1 to 12 and R.sup.5 represents a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms), a --C.sub.n H.sub.2n OR.sup.6 group (wherein R.sup.6 represents a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms and n represents an integer of from 2 to 12), or a ##STR2## group (wherein R.sup.7 and R.sup.8 each represent a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms and n is as hereinbefore defined), R.sup.2 represents a hydrogen atom or a methyl or ethyl group, R.sup.3 represents a single bond or an alkylene group containing from 1 to 4 carbon atoms, R.sup.4 represents a hydrogen atom, an alkyl group containing from 1 to 8 carbon atoms, a cycloalkyl group containing from 4 to 7 carbon atoms and unsubstituted or substituted by at least one alkyl group containing from 1 to 8 carbon atoms, or represents a phenyl or phenoxy group unsubstituted or substituted by at least one chlorine atom, trifluoromethyl group or alkyl group containing from 1 to 3 carbon atoms, and the wavy line attached to the C-11 and C-15 carbon atoms represents .alpha.- or .beta.- configuration or mixtures thereof] and cyclodextrin clathrates thereof, and, when R.sup.1 represents a hydrogen atom or a group C.sub.m H.sub.2m COOR.sup.5 in which R.sup.5 represents a hydrogen atom, non-toxic salts thereof and, when R.sup.1 represents a group ##STR3## non-toxic acid addition salts thereof, are new compounds and possess characteristic prostaglandin-like properties.

  通式为：##STR1##[其中，Y代表乙烯或顺式乙烯基，Z代表乙烯或顺式乙烯基，R.sup.1代表氢原子，含有1到12个碳原子的烷基，含有7到12个碳原子的芳基烷基，含有4到7个碳原子的环烷基，未取代或取代至少一个含有1到6个碳原子的烷基，未取代或取代至少一个氯原子、三氟甲基基团、含有1到4个碳原子的烷基或苯基的苯基，--C.sub.m H.sub.2m COOR.sup.5基团（其中m表示1到12的整数，R.sup.5表示氢原子或含有1到4个碳原子的烷基），--C.sub.n H.sub.2n OR.sup.6基团（其中R.sup.6表示氢原子或含有1到4个碳原子的烷基，n表示2到12的整数），或者##STR2##基团（其中R.sup.7和R.sup.8各自代表氢原子或含有1到4个碳原子的烷基，n如上所述），R.sup.2代表氢原子或甲基或乙基基团，R.sup.3代表单键或含有1到4个碳原子的烷基，R.sup.4代表氢原子，含有1到8个碳原子的烷基，含有4到7个碳原子的环烷基，未取代或取代至少一个含有1到8个碳原子的烷基，或者代表未取代或取代至少一个氯原子、三氟甲基基团或含有1到3个碳原子的烷基的苯基或苯氧基，连接到C-11和C-15碳原子的波浪线表示α-或β-构型或其混合物]及其环糊精包合物，当R.sup.1代表氢原子或C.sub.m H.sub.2m COOR.sup.5基团（其中R.sup.5代表氢原子）时，其非毒性盐，当R.sup.1代表##STR3##基团时，其非毒性酸加盐物是新的化合物，具有特征性的前列腺素样性质。
• US4215142A
  申请人：——

  公开号：US4215142A

  公开（公告）日：1980-07-29
• US4278688A
  申请人：——

  公开号：US4278688A

  公开（公告）日：1981-07-14