(4R)-4-hydroxymethyl-cyclopent-2-enone | 371783-68-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R)-4-hydroxymethyl-cyclopent-2-enone
• 英文别名: (4R)-4-(hydroxymethyl)cyclopent-2-en-1-one
• CAS: 371783-68-5
• 化学式: C₆H₈O₂
• 分子量: 112.128
• InChiKey: GDZDYXOTAFMJQH-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R)-4-hydroxymethyl-cyclopent-2-enone 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 9.0h， 生成 cis-3-Oxabicyclo<4.3.0>-nonane-4,8-dione
  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：

  (1S,4R)-(+)-4-(Hydroxymethyl)cyclopent-2-enol 在 4-(N,N-dimethylamino)pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以65%的产率得到(4R)-4-hydroxymethyl-cyclopent-2-enone
  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.