2-oxo-3-oxabicyclo<3.2.0>-6-heptene

• 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: 2-oxo-3-oxabicyclo<3.2.0>-6-heptene
• 英文别名: 3-oxabicyclo<3.2.0>hept-6-en-2-one；3-oxabicyclo[3.2.0]hept-6-en-2-one；(1S,5R)-3-oxabicyclo[3.2.0]hept-6-en-2-one
• 化学式: C₆H₆O₂
• 分子量: 110.112
• InChiKey: GBGUHVWSHULMEC-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-oxo-3-oxabicyclo<3.2.0>-6-heptene 在 palladium on activated charcoal 氢气 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以89%的产率得到(+)-(1S,5R)-3-oxabicyclo<3,2,0>heptan-2-one
  参考文献：
  名称：

  （1R，2S）-（+）-顺-1-甲氧基羰基-2-甲基环丁烷的合成，拆分和绝对立体化学

  摘要：

  分五个步骤有效地制备了未被反式异构体污染的外消旋顺式-1-甲氧基羰基-2-甲基环丁烷。从（R）-（-）-苯基甘醇中分离出相应的酰胺。由（+）-顺式-1-甲氧基羰基-2-甲基环丁烷的酰胺的X射线晶体结构测定表明，它具有（1R，2S）绝对立体化学，构型分配的修正。

  DOI：

  10.1021/jo0009550
• 作为产物：
  描述：

  cis-3-cyclobutene-1,2-dicarboxylic acid monomethyl ester 在 盐酸 、 氢氧化钾 、 sodium tetrahydroborate 、 calcium chloride 作用下， 以 乙醇 为溶剂， 反应 18.5h， 生成 2-oxo-3-oxabicyclo<3.2.0>-6-heptene
  参考文献：
  名称：

  环丁烯的制备和环电开环：取代共轭二烯和三烯的立体控制方法

  摘要：

  4-烷基-2-环丁烯-1-碳醛在低温下发生热电开环，仅生成（2 Z，4 E）-链二烯醛，该方法用于顺式-3-环丁烯-1，2的转化。-二甲醇1转化为各种天然存在的1,3,5-链烷烃和2,4-癸二烯酸酯。的去对称1与荧光假单胞菌的脂肪酶可以访问-3-氧杂二环[3.2.0]庚-6-烯-2-酮的两种对映体4，用于立体控制路由使用至6-含氧（2 Ž，4 ë）-alkadienals 。

  DOI：

  10.1016/0040-4020(96)00039-7

文献信息

• The addition of organometallic reagents to 3-oxabicyclo[3.2.0]hept-6-en-2-ol: A stereoselective route to 6-oxygenated (2Z,4E)-alkadienals
  作者：Kevin J. Hodgetts、Christopher J. Wallis、Timothy W. Wallace

  DOI：10.1016/s0040-4039(00)60752-9

  日期：1994.6

  The additions of various organometallic species to 3-oxabicyclo[3.2.0]hept-6-en-2-ol are diastereoselective; the results are consistent with addition to the less hindered face of a metal-chelated form of the corresponding γ-hydroxyaldehyde.

  向3-氧杂双环[3.2.0] hept-6-en-2-ol中添加各种有机金属是非对映选择性的。结果与相应的γ-羟醛的金属螯合形式的受阻面较小相符。
• Total Synthesis and Bioactivity of Resolvin E2
  作者：Seiji Ogawa、Daisuke Urabe、Yoshiyuki Yokokura、Hiroyuki Arai、Makoto Arita、Masayuki Inoue

  DOI：10.1021/ol901350g

  日期：2009.8.20

  Resolvin E2 is a potent anti-inflammatory compound, derived from eicosapentaenoic acid. The efficient total synthesis of resolvin E2 by taking advantage of its intrinsic pseudoenantiomeric substructures is reported. The synthetic resolvin E2 proved to be biologically active in blocking neutrophil Infiltration and reducing proinflammatory cytokines in the acute peritonitis model.
• Enantioselective synthesis of (+)-3-oxabicyclo[3.2.0]hept-6-en-2-one
  作者：Marie-Edith Gourdel-Martin、Corinne Comoy、François Huet

  DOI：10.1016/s0957-4166(99)00015-4

  日期：1999.2

  The title compound was obtained in 99.3% ee by enzymatic oxidation of cis-2-cyclobutene-1,4-bis(hydroxymethyl) in the presence of horse liver alcohol dehydrogenase. Another route was through desymmetrisation of cis-cyclobut-3-ene-1,2-dicarboxylic anhydride with (-)-pantolactone, (C) 1999 Elsevier Science Ltd. All rights reserved.
• High selectivities in electrophilic additions to cyclobutene compounds
  作者：Laurence Mévellec、Michel Evers、François Huet

  DOI：10.1016/s0040-4020(96)00945-3

  日期：1996.11

  Epoxidation of 2, 3, 4 with m-CPBA mainly led to the cis-attack products whereas 1 and 6 led to the other selectivity. The result was reversed, from 4, with Payne's reagent Bromohydroxylation of 4 involved an intermediate bromonium ion syn to the substituents. Haloselenylations occurred with the syn-selectivity from 1, 2, 3 and 4, to the anti-selectivity from 6, and without selectivity from 5. NOE enhancement measurements and several chemical correlations led to the stereochemical assignments. Formation of the intramolecular reaction products 24 and 25 was also pointed out. Copyright (C) 1996 Elsevier Science Ltd
• Synthesis of<i>cis</i>-Disubstituted Cyclobutenyl Nucleoside Analogues
  作者：M-E. Gourdel-Martin、F. Huet

  DOI：10.1080/15257779908041527

  日期：1999.4

  cis-Disubstituted cyclobutene nucleosides analogues were prepared by a linear synthesis starting from cis-cyclobutene dicarboxylic anhydride. This strategy involved mild reaction conditions with intent to restrict the thermal electrocyclic ring opening into (Z,E)-dienes.