4H-环氧乙烷[3,4]环戊丙[1,2-b]呋喃-酮,六氢,(1aR,2aS,5a,5b)- | 54483-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 中文名称: 4H-环氧乙烷[3,4]环戊丙[1,2-b]呋喃-酮,六氢,(1aR,2aS,5a,5b)-
• 英文名称: (1aS,2aR,5aR,5bR)-hexahydro-4H-oxireno[3,4]cyclopenta[1,2-b]furan-4-one
• 英文别名: (1aS,2aR,5aR,5bR)-Tetrahydro-1aH-oxireno[2',3':3,4]cyclopenta[1,2-b]furan-4(5bH)-one；(1R,2R,4S,6R)-3,7-dioxatricyclo[4.3.0.02,4]nonan-8-one
• CAS: 54483-30-6
• 化学式: C₇H₈O₃
• 分子量: 140.139
• InChiKey: MUIDESAARNCREM-YCHQMNKZSA-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：

  4H-环氧乙烷[3,4]环戊丙[1,2-b]呋喃-酮,六氢,(1aR,2aS,5a,5b)- 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 methyl (Z)-7-[(1R,2R,3R,5S)-3-hydroxy-6-oxabicyclo[3.1.0]hexan-2-yl]hept-5-enoate
  参考文献：
  名称：

  一种强效血栓烷A 2拮抗剂的全合成

  摘要：

  据报道，强大的血栓烷A 2拮抗剂3（EC 50 3 nM）的合成。

  DOI：

  10.1016/s0040-4039(00)97481-1
• 作为产物：
  描述：

  3,3-dichloro-6,6a-dihydro-3aH-cyclopenta[b]furan-2-one 在 2-羟基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 锌铜偶 、 氯化铵 作用下， 以 四氢呋喃 、 甲醇 、 水 、 苯 为溶剂， 反应 77.0h， 生成 4H-环氧乙烷[3,4]环戊丙[1,2-b]呋喃-酮,六氢,(1aR,2aS,5a,5b)-
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2015.10.106

文献信息

• Gombos, Zsuzsanna; Nyitrai, J.; Nagy, J., ACH - Models in Chemistry, 1994, vol. 131, # 3-4, p. 327 - 336
  作者：Gombos, Zsuzsanna、Nyitrai, J.、Nagy, J.、Sohar, P.、Balogh, Gy.、Brlik, J.

  DOI：——

  日期：——
• Bromohydrin reactions of Grieco’s bicyclic lactone
  作者：Rodolfo Tello-Aburto、Maria Yolanda Rios、Dale C. Swenson、Horacio F. Olivo

  DOI：10.1016/j.tetlet.2008.09.081

  日期：2008.11

  The bromohydrin reaction in Grieco's bicyclic lactone 1 was reinvestigated. Two regioisomeric bromohydrins were obtained (2 and 8), and their configurations were unambiguously determined by X-ray diffraction analyses. (c) 2008 Elsevier Ltd. All rights reserved.
• MIZUNO AKIRA; YASUMASA HAMADA; SHIORI TAKAYUKI, CHEM. AND PHARM. BULL., 1981, 29, NO 6, 1774-1776
  作者：MIZUNO AKIRA、 YASUMASA HAMADA、 SHIORI TAKAYUKI

  DOI：——

  日期：——
• 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