7-Oxabicyclo<2.2.1>hept-5-en-endo-2,endo-3-diol | 102681-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 7-Oxabicyclo<2.2.1>hept-5-en-endo-2,endo-3-diol
• 英文别名: endo-7-oxabicyclo<2.2.1>hept-5-ene-2,3-diol；cis-endo-7-oxabicyclo[2.2.1]hept-5-ene-2,3-diol；endo-7-oxabicyclo[2.2.1]hept-5-ene-2,3-diol；(1R,2R,3S,4S)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-diol
• CAS: 102681-38-9
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: YATRXMNGSLWFHT-GUCUJZIJSA-N

物化性质

• 熔点：
  100 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  275.6±40.0 °C(Predicted)
• 密度：
  1.534±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-Oxabicyclo<2.2.1>hept-5-en-endo-2,endo-3-diol 在 4-二甲氨基吡啶 lipase of Candida cylindracea 、 三乙胺 作用下， 反应 29.0h， 生成 [(1S,2R,3S,4R)-3-acetyloxy-7-oxabicyclo[2.2.1]hept-5-en-2-yl] prop-2-enoate
  参考文献：
  名称：

  A Concise Approach to the 5-Oxo-6,7-Dihydrofuranopyrone Skeleton

  摘要：

  本文介绍了从呋喃中提取 3-乙酰氧基-5-氧代-6,7-二氢呋喃吡喃酮骨架的高效立体选择性路线。该方法的关键步骤包括对中二元醇 5a 进行酶解不对称反应，以及在方便取代的衍生物 3 上实现 ROM-CM-RCM 序列。

  DOI：

  10.1055/s-2006-933143
• 作为产物：
  描述：

  endo-3,5,10-Trioxatricyclo<5.2.1.0^2,6>dec-8-en-4-on 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以96%的产率得到7-Oxabicyclo<2.2.1>hept-5-en-endo-2,endo-3-diol
  参考文献：
  名称：

  2,3,4,5-四取代四氢呋喃衍生物的简单合成

  摘要：

  2,3,4,5-四取代四氢呋喃从呋喃通过 7-oxabicyclo[2.2.1]hept-5-ene-2,3-diol (2,3-dihydroxy-7-oxorobomene) 衍生物的简明合成是报道。这些转化的关键步骤是氧二环化合物在乙烯存在下并使用市售的第二代 Hoveyda-Grubbs 催化剂进行序列开环复分解 - 交叉复分解 (ROM-CM) 反应。

  DOI：

  10.1055/s-0028-1083180

文献信息

• A Convenient Approach to Polycyclic Derivatives with a<i>cis</i>-Fused 2,6-Dioxabicyclo[4.3.0]nonane System by the Sequence Ring-Opening/Intramolecular Ring-Closing Enyne Metathesis/Diels-Alder Reaction
  作者：Ana Aljarilla、Maria C. Murcia、Aurelio G. Csákÿ、Joaquín Plumet

  DOI：10.1002/ejoc.200800936

  日期：2009.2

  7-Oxanorbornene derivatives functionalized with alkyneappendages undergo intramolecular enyne metathesis reactions to give cis-fused 2,6-dioxabicyclo[4.3.0]nonane derivatives. These compounds have a diene functionality thatallows their reaction with dienophiles (N-phenylmaleimide) to yield densely functionalized polycyclic compounds. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  用炔烃附属物官能化的 7-氧代降冰片烯衍生物进行分子内烯炔复分解反应，得到顺式稠合的 2,6-二氧杂双环 [4.3.0] 壬烷衍生物。这些化合物具有二烯官能团，允许它们与亲二烯体（N-苯基马来酰亚胺）反应以产生密集官能化的多环化合物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Prinzbach, Horst; Bringmann, Horst; Markert, Juergen, Chemische Berichte, 1986, vol. 119, # 2, p. 589 - 615
  作者：Prinzbach, Horst、Bringmann, Horst、Markert, Juergen、Fischer, Gerhard、Knothe, Lothar、et al.

  DOI：——

  日期：——
• Living ring-opening metathesis polymerization of 2,3-difunctionalized 7-oxanorbornenes and 7-oxanorbornadienes by Mo(CHCMe2R)(NC6H3-iso-Pr2-2,6)(O-tert-Bu)2 and Mo(CHCMe2R)(NC6H3-iso-Pr2-2,6)(OCMe2CF3)2
  作者：Guillermo C. Bazan、John H. Oskam、Hyun Nam Cho、Lee Y. Park、Richard R. Schrock

  DOI：10.1021/ja00018a028

  日期：1991.8

  7-Oxabenzonorbornadiene (9), 2,3-endo-cis-diacetoxy-7-oxanorbornene, and 2,3-endo-cis-(isopropylidenedioxy)-7-oxanorbornene can be polymerized by Mo(CHCMe2R)(NAr)(O-t-Bu)2 (Ar = 2,6-C6H3-i-Pr2; R = CH3, C6H5) ([Mo]-(CHCMe2R)) to give polymers with narrow molecular weight distributions (PDI < 1.17). However, 2,3-bis(trifluoromethyl)-7-oxanorbornadiene (1), 2,3-dicarbomethoxy-7-oxanorbornadiene (4), and 2,3-trans-dicyano-7-oxanorborn-5-ene (12) form stable metallacycles upon addition to [Mo](CHCMe2R). The rate of reaction of 1 with [Mo](CHCMe2R) has been determined qualitatively to be comparable to that of norbornene in competition experiments, a result that implies that the lone pair on the oxygen in the 7-position is accelerating metallacycle formation. The metallacycle that results from addition of 1 to [Mo](CHCMe2Ph) is square pyramidal with the imido ligand in the apical position. (Crystal data for 2b: a = 12.420 (3) angstrom, b = 15.466 (4) angstrom, c = 20.856 (6) angstrom, V = 3852 (2) angstrom 3, beta = 105.97 (2)degrees, space group = P2(1)/n, Z = 4, M(r) = 779.76, rho = 1.345 g/cm3, mu = 3.9 cm-1, R1 = 0.049, R2 = 0.068.) The MoC3 ring is planar with the CMe2Ph group pointed toward the imido ligand and the C-7 frame of the monomer pointed away from it (a trans metallacyclic ring). The oxygen in the 7-position of the norbornene moiety is located 3.332 (4) angstrom from the metal. Electronic and steric factors that influence first-order breakup of the metallacycle have been studied for monomers 1 and 4. The more reactive catalyst, Mo(CHCMe2Ph)(NAr)(OCMe2CF3)2, can polymerize 1, 4, and 12 to give polymers with narrow molecular weight distributions (PDI < 1.15).
• De Micheli; De Amici; Grana, Il Farmaco, 1993, vol. 48, # 10, p. 1333 - 1348
  作者：De Micheli、De Amici、Grana、Zonta、Giannella、Piergentili

  DOI：——

  日期：——
• PRINZBACH, H.;BINGMANN, H.;MARKERT, J.;FISCHER, G.;KNOTHE, L.;EBERBACH, W+, CHEM. BER., 1986, 119, N 2, 589-615
  作者：PRINZBACH, H.、BINGMANN, H.、MARKERT, J.、FISCHER, G.、KNOTHE, L.、EBERBACH, W+

  DOI：——

  日期：——