(1S,5R)-6-hydroxymethyl-2-oxabicyclo[3.3.0]oct-6-en-3-one | 62158-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,5R)-6-hydroxymethyl-2-oxabicyclo[3.3.0]oct-6-en-3-one
• 英文别名: 6-Hydroxymethyl-2-oxabicyclo<3.3.0>oct-6-en-3-on；6-Hydroxymethyl-2-oxabicyclo[3.3.0]oct-6-en-3-on；(3aR,6aS)-4-(hydroxymethyl)-3,3a,6,6a-tetrahydrocyclopenta[b]furan-2-one
• CAS: 62158-44-5
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: MZXPOWWJNHCNQF-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,5R)-6-hydroxymethyl-2-oxabicyclo[3.3.0]oct-6-en-3-one 在 platinum(IV) oxide 吡啶 、 2,6-二甲基吡啶 、 lead(IV) acetate 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 samarium diiodide 、 copper diacetate 、 草酰氯 、 D-(-)-酒石酸二乙酯 、 氢气 、 lithium carbonate 、 二异丁基氢化铝 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 、 氯苯 为溶剂， -78.0~125.0 ℃ 、413.68 kPa 条件下， 反应 67.91h， 生成 12-epi-PGF_2α
  参考文献：
  名称：

  Enantioselective Synthesis of 12-epi-PGF_2α and 12,15-diepi-PGF_2α

  摘要：

  An enantioselective synthesis of 12-epi-PGF(2 alpha), (3) and 12,15-diepi-PGF(2 alpha) (4), PG-like compounds that are probably generated in vivo by nonenzymatic, free-radical-induced peroxidation of arachidonic acid, has been achieved starting from the commercially available Corey lactone (9). The key strategy involves SmI2 reduction of the gamma,delta-epoxy-alpha,beta-unsaturated ester 7, followed by in situ trapping with hexanal; subsequent hydrogenation and decarboxylation affords the stereoselective construction of the lower side chain. This new method is expected to provide a convenient access to various PG-like isoprostanes derived from oxidation of arachidonic acid and cis-4,7,10,13,16,19-docosahexaenoic acid.

  DOI：

  10.1021/jo990906r
• 作为产物：
  描述：

  (1S,5S)-3-oxo-2-oxabicyclo<3.3.0>oct-6-en-6-carbaldehyde 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 以96%的产率得到(1S,5R)-6-hydroxymethyl-2-oxabicyclo[3.3.0]oct-6-en-3-one
  参考文献：
  名称：

  Enantioselective Synthesis of 12-epi-PGF_2α and 12,15-diepi-PGF_2α

  摘要：

  An enantioselective synthesis of 12-epi-PGF(2 alpha), (3) and 12,15-diepi-PGF(2 alpha) (4), PG-like compounds that are probably generated in vivo by nonenzymatic, free-radical-induced peroxidation of arachidonic acid, has been achieved starting from the commercially available Corey lactone (9). The key strategy involves SmI2 reduction of the gamma,delta-epoxy-alpha,beta-unsaturated ester 7, followed by in situ trapping with hexanal; subsequent hydrogenation and decarboxylation affords the stereoselective construction of the lower side chain. This new method is expected to provide a convenient access to various PG-like isoprostanes derived from oxidation of arachidonic acid and cis-4,7,10,13,16,19-docosahexaenoic acid.

  DOI：

  10.1021/jo990906r

文献信息

• A new synthesis of (+)-didemnenones A and B
  作者：Tsutomu Sugahara、Tomoko Ohike、Motohiro Soejima、Seiichi Takano

  DOI：10.1039/p19900001824

  日期：——

  (+)-Didemnenones A (1) and B (2), unique and biologically active C11-cyclopentenone metabolites from a tunicate, were synthesized from the optically active lactone (4).

  从光学活性内酯（4）合成了（+）-二烯烯酮A（1）和B（2），一种来自被膜的独特且具有生物活性的C 11-环戊烯酮代谢物。
• SUGAHARA, TSUTOMU;OHIKE, TOMOKO;SOEJIMA, MOTOHIRO;TAKANO, SEIICHI, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 1824-1826
  作者：SUGAHARA, TSUTOMU、OHIKE, TOMOKO、SOEJIMA, MOTOHIRO、TAKANO, SEIICHI

  DOI：——

  日期：——
• Enantioselective Synthesis of 12-<i>epi</i>-PGF₂_α and 12,15-<i>diepi</i>-PGF₂_α
  作者：Sheng Lai、Dongreyoul Lee、Jong Sun U、Jin Kun Cha

  DOI：10.1021/jo990906r

  日期：1999.9.1

  An enantioselective synthesis of 12-epi-PGF(2 alpha), (3) and 12,15-diepi-PGF(2 alpha) (4), PG-like compounds that are probably generated in vivo by nonenzymatic, free-radical-induced peroxidation of arachidonic acid, has been achieved starting from the commercially available Corey lactone (9). The key strategy involves SmI2 reduction of the gamma,delta-epoxy-alpha,beta-unsaturated ester 7, followed by in situ trapping with hexanal; subsequent hydrogenation and decarboxylation affords the stereoselective construction of the lower side chain. This new method is expected to provide a convenient access to various PG-like isoprostanes derived from oxidation of arachidonic acid and cis-4,7,10,13,16,19-docosahexaenoic acid.