(3aR,4R,5S,6aR)-acetic acid 4-acetoxymethyl-6-iodo-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester | 371783-85-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3aR,4R,5S,6aR)-acetic acid 4-acetoxymethyl-6-iodo-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester
• 英文别名: [(3aR,4R,5S,6S,6aR)-5-acetyloxy-6-iodo-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-yl]methyl acetate
• CAS: 371783-85-6
• 化学式: C₁₂H₁₅IO₆
• 分子量: 382.152
• InChiKey: KVZNCZKJJKNWAF-GATYQTQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,4R,5S,6aR)-acetic acid 4-acetoxymethyl-6-iodo-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以91%的产率得到(3aR,4R,5R,6aS)-(-)-acetic acid 5-acetoxy-2-oxo-hexahydro-cyclopenta[b]furan-4-ymethyl ester
  参考文献：
  名称：

  Enantioselective synthesis of cis-1,2-dialkyl substituted cyclopentanoid and isoprostane building blocks via 6-exo-trigonal radical cyclizations

  摘要：

  Two different 6-exo-trigonal cyclizations of enantiomerically enriched 6-heptenyl radicals readily afforded versatile synthetic precursors of cis-1,2-dialkyl substituted cyclopentane derivatives. Starting from one of these intermediates, we accomplished an enantiospecific formal synthesis of two important isoprostanes, namely 15-F-2c-IsoP and ent-15-F-2c-IsoP. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00312-3
• 作为产物：
  描述：

  乙酸酐 、 [(3aR,4R,6aS)-2-oxo-3,3a,4,6a-tetrahydrocyclopenta[b]furan-4-yl]methyl acetate 在 一氯化碘 、 吡啶 、 4-二甲氨基吡啶 作用下， 以 水 、 乙腈 、 二氯甲烷 为溶剂， 反应 4.5h， 以89%的产率得到(3aR,4R,5S,6aR)-acetic acid 4-acetoxymethyl-6-iodo-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester
  参考文献：
  名称：

  Enantioselective synthesis of cis-1,2-dialkyl substituted cyclopentanoid and isoprostane building blocks via 6-exo-trigonal radical cyclizations

  摘要：

  Two different 6-exo-trigonal cyclizations of enantiomerically enriched 6-heptenyl radicals readily afforded versatile synthetic precursors of cis-1,2-dialkyl substituted cyclopentane derivatives. Starting from one of these intermediates, we accomplished an enantiospecific formal synthesis of two important isoprostanes, namely 15-F-2c-IsoP and ent-15-F-2c-IsoP. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00312-3

文献信息

• Enantioselective synthesis of cis-1,2-dialkyl substituted cyclopentanoid and isoprostane building blocks via 6-exo-trigonal radical cyclizations
  作者：Giuseppe Zanoni、Savino Re、Alessia Meriggi、Francesca Castronovo、Giovanni Vidari

  DOI：10.1016/s0957-4166(01)00312-3

  日期：2001.7

  Two different 6-exo-trigonal cyclizations of enantiomerically enriched 6-heptenyl radicals readily afforded versatile synthetic precursors of cis-1,2-dialkyl substituted cyclopentane derivatives. Starting from one of these intermediates, we accomplished an enantiospecific formal synthesis of two important isoprostanes, namely 15-F-2c-IsoP and ent-15-F-2c-IsoP. (C) 2001 Elsevier Science Ltd. All rights reserved.