7-oxabicyclo[2.2.1]hept-5-en-2,3-dicarbonitrile | 6636-33-5

• 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-2,3-dicarbonitrile
• 英文别名: (+/-)-7-oxa-norborn-5-ene-2endo,3exo-dicarbonitrile；(+/-)-7-Oxa-norborn-5-en-2endo,3exo-dicarbonitril；(1S,2R,3R,4R)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarbonitrile
• CAS: 6636-33-5；29265-33-6；85799-31-1
• 化学式: C₈H₆N₂O
• 分子量: 146.148
• InChiKey: HIUQDZTXJVLYOQ-DKXJUACHSA-N

物化性质

• 沸点：
  380.4±42.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 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：
  56.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-oxabicyclo[2.2.1]hept-5-en-2,3-dicarbonitrile 在 四氧化锇 、 双氧水 、 对甲苯磺酸 作用下， 以 乙醚 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 78.0h， 生成 4,4-dimethyl-3,5,10-trioxatricyclo[5.2.1.0^2,6]decane-8,9-dicarbonitrile
  参考文献：
  名称：

  新型双环抗肿瘤铂（IV）配合物的合成，生物学评估和SAR研究

  摘要：

  本研究描述了具有1,2-双（氨基甲基）碳双环或氧双环载体配体的新型铂（IV）配合物的合成，抗癌活性和SAR研究，这些配体在轴向位置带有氯和/或氢氧配体，而氯代或丙二酸配体则位于赤道位置（不稳定的配体）。合成这些复合物的目的是获得新的抗癌原理，使其更易溶于水，因此具有更高的生物利用度。为了评估其抗增殖活性并建立结构-活性关系规则，已经设计了铂原子上的几种取代模式。通过K 2 Pt（OH）2 Cl 4的反应合成在铂（IV）上具有轴向羟基配体的铂（IV）配合物与相应的二胺。通过二胺与K 2 PtCl 6的直接反应合成了在铂（IV）原子上具有轴向氯代配体的配合物。羧基化的配合物是通过赤道氯代配体与二羧酸银的取代反应合成的。活性最高的络合物是具有丙二酸酯作为不稳定配体的那些，无论载体配体的结构如何。关于不稳定的1,4-二胺载体配体的结构对细胞毒性的影响，发现具有更亲脂性和对称性的双环[2.2.2]辛

  DOI：

  10.1016/j.ejmech.2014.06.042
• 作为产物：
  描述：

  呋喃 、 反丁烯二腈 以85%的产率得到7-oxabicyclo[2.2.1]hept-5-en-2,3-dicarbonitrile
  参考文献：
  名称：

  Synthesis, Biophysical Studies, and Antiproliferative Activity of Platinum(II) Complexes Having 1,2-Bis(aminomethyl)carbobicyclic Ligands

  摘要：

  A selected chemical library of six platinum(II) complexes having 1,2-bis(aminomethyl)carbobicyclic ligands were synthesized after a rational design in order to evaluate their antiproliferative activity and the structure-activity relationships. The cytotoxicity studies were performed using cancer cell lines sensitive (A2780) and resistant (A2780R) to cisplatin. Excellent cytotoxicity was observed for most of complexes, which presented better resistance factors than cisplatin against the A2780R cell line. The interaction of these complexes with DNA, as the target biomolecule, was evaluated by several methods: DNA-platinum binding kinetics, changes in the DNA melting temperature, evaluation of the unwinding angle of supercoiled DNA, evaluation of the interstrand cross-links, and replication mapping. The kinetics of the interaction with glutathione was also investigated to better understand the resistant factors observed for the new complexes.

  DOI：

  10.1021/jm070844u

文献信息

• The diels-alder reaction of 2,5-dialkylfurans and fumaronitrile revisited
  作者：Michael J. Cook、Steven J. Cracknell

  DOI：10.1016/s0040-4020(01)89565-x

  日期：1994.1

  The equilibrium reactions of furan and six 2,5-dialkyl derivatives with fumaronitrile were investigated under standard conditions (3.0 x 10(-4) M) at four different temperatures in chloroform-d as solvent. Plots of InK against 1/T were linear for each member of the series. The results show that the equilibrium concentration of adduct is sensitive to substituents. At equilibrium, there is a greater proportion of adduct derived from 2,5-dimethylfuran than from furan itself. However, as the length of the substituent chains is increased, the proportion of adduct decreases. Similar trends are also apparent from a more limited study of the equilibria in methanol-d(4) and acetone-d(6) as solvents. The concentrations of adduct in the equilibrium mixtures are highest in chloroform-d and lowest in acetone-d(6). AM1 calculations are reported for model adduct structures.
• Unsaturated Nitriles. IV. Adducts of Dienes with Fumaronitrile¹
  作者：David T. Mowry

  DOI：10.1021/ja01195a032

  日期：1947.3
• 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).