(1aR,2aS,5aS,5bS)-hexahydro-4H-oxireno[3,4]cyclopenta[1,2-b]furan-4-one | 59829-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (1aR,2aS,5aS,5bS)-hexahydro-4H-oxireno[3,4]cyclopenta[1,2-b]furan-4-one
• 英文别名: rel-(1aR,2aS,5aS,5bS)-Hexahydro-4H-oxireno[2',3':3,4]cyclopenta[1,2-b]furan-4-one；(1S,2S,4R,6S)-3,7-dioxatricyclo[4.3.0.02,4]nonan-8-one
• CAS: 59829-44-6
• 化学式: C₇H₈O₃
• 分子量: 140.139
• InChiKey: MUIDESAARNCREM-HHJANIIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-辛炔 、 (1aR,2aS,5aS,5bS)-hexahydro-4H-oxireno[3,4]cyclopenta[1,2-b]furan-4-one 生成 5-hydroxy-1-(2-oxo-3-nonynyl)-2,3-epoxycyclopentane 、 (3aR,4S,5R,6aS)-5-Hydroxy-4-oct-1-ynyl-hexahydro-cyclopenta[b]furan-2-one
  参考文献：
  名称：

  Lopp, M. I.; Payu, A. Yu.; Niidas, P. Ya., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 11.1, p. 2086 - 2093

  摘要：

  DOI：
• 作为产物：
  描述：

  前列腺素中间体 在 双氧水 、 焦碳酸二乙酯 作用下， 以 二氯甲烷 为溶剂， 生成 (1aR,2aS,5aS,5bS)-hexahydro-4H-oxireno[3,4]cyclopenta[1,2-b]furan-4-one
  参考文献：
  名称：

  Mizuno, Akira; Hamada, Yasumasa; Shioiri, Takayuki, Chemical and pharmaceutical bulletin, 1981, vol. 29, # 6, p. 1774 - 1776

  摘要：

  DOI：

文献信息

• A general route to optically pure prostaglandins from a D-glucose derivative
  作者：Robert J. Ferrier、Petpiboon Prasit

  DOI：10.1039/c39810000983

  日期：——

  The epoxy-lactone (14), which is a key intermediate in one synthetic route to prostaglandins, has been prepared from a readily available D-glucose derivative.

  环氧内酯（14）是前列腺素的一种合成途径中的关键中间体，它是由一种容易获得的D-葡萄糖衍生物制备的。
• Ferrier, Robert J.; Prasit, Petpiboon; Gainsford, Graeme J., Journal of the Chemical Society. Perkin transactions I, 1983, # 8, p. 1629 - 1634
  作者：Ferrier, Robert J.、Prasit, Petpiboon、Gainsford, Graeme J.

  DOI：——

  日期：——
• Tandem transformations of cyclopentene α,α-dichlorocarboxamides into epoxy lactones induced by a γ-hydroxyl group; a short synthesis of the Corey epoxy lactone and its enantiomer
  作者：Zuleykha R. Valiullina、Vera A. Akhmetyanova、Nadezhda A. Ivanova、Mansur S. Miftakhov

  DOI：10.1016/j.tetlet.2015.10.106

  日期：2015.12

  The stable iminolactone 6 was obtained by NBS induced bromocyclization of carboxamide 4. Under treatment of 6 with DBU a tandem recyclization transformation occurred resulting in the formation of epoxyiminolactone 7. Bromo(iodo)cyclization of 4 in aqueous organic medium followed by treatment with base gave epoxylactone 9. Under the optimized conditions, Corey epoxylactone 1 and its enantiomer eat-1 were obtained from diastereomeric carboxamides 4 and 5 in an overall yield of 40%. (C) 2015 Elsevier Ltd. All rights reserved.
• Haloiminolactonization of cyclopentene α,α-dichlorocarboxamides. Tandem rearrangement of iminolactones in epoxylactones
  作者：Z. R. Valiullina、V. A. Akhmet’yanova、N. A. Ivanova、A. S. Erastov、E. S. Meshcheryakova、M. S. Miftakhov

  DOI：10.1134/s1070428015110020

  日期：2015.11

  Electrophilic cyclization initiated by NBS and I-2 of 2,2-dichloro-2-[(1R,5S)- and 2,2-dichloro-2-[(1S,5R)-5-hydroxy-2-cyclopent-2-en-1-yl]-N-[(1R)-1-phenylethyl]acetamides was investigated. Stable under conditions of chromatography on SiO2 bicyclic iminoesters, (2Z,3aS,4S,6S,6aS)-6-bromo-3,3-dichloro- and (2Z,3aS,4S,6S,6aS)-3,3-dichloro-6-iodo-2-[(1R)-1-phenylethyl]imino}hexahydro-2H-cyclopenta[b]furan-4-ols were isolated and characterized, and a possible version was suggested of their step-by-step recyclization transformations. The halocyclization of carboxamides in water-organic mixtures afforded bicyclic epoxylactones (1aR,2aS,5aS,5bS)- and (1aS,2aR,5aR,5bR)-5,5-dichlorohexahydro-4H-oxireno[3,4]cyclopenta-[1,2-b]furan-4-ones, whose reductive dechlorination proceeded stepwise with successive removal of Cl atoms and led to the formation of (1aR,2aS,5aS,5bS)- and (1aS,2aR,5aR,5bR)-hexahydro-4H-oxireno[3,4]cyclopenta-[1,2-b]furan-4-ones.
• US3933892A
  申请人：——

  公开号：US3933892A

  公开（公告）日：1976-01-20