7-Oxa-bicyclo-<2.2.1>-hept-5-en-2,3-exo,exo-dicarbonsaeure | 28871-62-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 7-Oxa-bicyclo-<2.2.1>-hept-5-en-2,3-exo,exo-dicarbonsaeure
• 英文别名: 7-Oxa-bicyclo<2.2.1>hept-5-en-2-exo,3-cis-dicarbonsaeure；exo-7-oxabicyclo-[2.2.1]-5-heptene-2,3-dicarboxylic acid；exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic acid；7-oxa-bicyclo[2.2.1]hept-5-ene-2exo,3exo-dicarboxylic acid；7-oxa-norborn-5-ene-2exo,3exo-dicarboxylic acid；7-Oxa-norborn-5-en-2exo,3exo-dicarbonsaeure；(1S,2R,3S,4R)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid
• CAS: 28871-62-7
• 化学式: C₈H₈O₅
• 分子量: 184.149
• InChiKey: ROWKCXLLOLDVIO-FBXFSONDSA-N

物化性质

• 熔点：
  129°C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38

反应信息

• 作为反应物：
  描述：

  7-Oxa-bicyclo-<2.2.1>-hept-5-en-2,3-exo,exo-dicarbonsaeure 在 ammonium hydroxide 、 potassium carbonate 作用下， 以 水 为溶剂， 生成 2-hydroxymethyl-(3at,7at)-3a,4,7,7a-tetrahydro-4r,7c-epioxido-isoindole-1,3-dione
  参考文献：
  名称：

  Zawadowski,T. et al., Roczniki Chemii, 1973, vol. 47, p. 189 - 191

  摘要：

  DOI：
• 作为产物：
  描述：

  exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride 在 水 作用下， 以98%的产率得到7-Oxa-bicyclo-<2.2.1>-hept-5-en-2,3-exo,exo-dicarbonsaeure
  参考文献：
  名称：

  Novel Fluorescent Probes for Singlet Oxygen

  摘要：

  The first fluorescent chemical traps for (1)O(2) have been developed. DPAXs react specifically with (1)O(2) to yield the corresponding endoperoxides, DPAX-EPs (see scheme; X = H, Cl, F). DPAXs scarcely fluoresce, while DPAX-EPs are strongly fluorescent. Since the fluorescence of these probes is unaffected by H(2)O(2), superoxide, and nitric oxide, they are useful for the selective detection of (1)O(2) in biological systems.

  DOI：

  10.1002/(sici)1521-3773(19991004)38:19<2899::aid-anie2899>3.0.co;2-m

文献信息

• Titanium Isopropoxide Promoted Tandem Self-Cross and Ring-Closing Metathesis Approach for the Synthesis of Macrotetralides
  作者：Sengodagounder Muthusamy、Datshanamoorthy Azhagan

  DOI：10.1002/ejoc.201301239

  日期：2014.1

  A new approach is demonstrated for the synthesis of macrotetralides through an olefin metathesis reaction using Grubbs' second-generation catalyst with titanium isopropoxide as a cocatalyst. This study demonstrates a tandem self-cross and ring-closing metathesis approach to form macrocyclic ring systems with excellent (E) selectivity. The reaction was optimized with regard to functional group, catalyst

  展示了一种通过烯烃复分解反应合成大环四内酯的新方法，使用 Grubbs 的第二代催化剂和异丙醇钛作为助催化剂。该研究展示了一种串联的自交叉和闭环复分解方法，以形成具有优异 (E) 选择性的大环系统。该反应在官能团、催化剂、溶剂、路易斯酸、浓度和温度方面进行了优化。
• Water-Soluble and Water-Insoluble, Ring Opening Metathesis Polymerization Products, Monomers and Related Methods
  申请人：Tew Gregory N.

  公开号：US20090082524A1

  公开（公告）日：2009-03-26

  The invention provides certain novel water-soluble and water-insoluble monomers for ring opening metathesis polymerization and novel polymers, compositions and products, and related methods thereof.

  这项发明提供了用于环氧烯烃开环重聚合的某些新型水溶性和不溶性单体，以及新型聚合物、组合物和产品，以及相关方法。
• Diels-Alder reaction of furan with some dienophiles
  作者：T.A. Eggelte、H. de Koning、H.O. Huisman

  DOI：10.1016/s0040-4020(01)93382-4

  日期：1973.1

  The reaction of furan and maleic acid was carried out in several solvents. The endo-adduct was isolated and the structure established by its spectral properties and conversion into known compounds. The adducts of furan with fumaric acid, diethyl fumarate and diethyl maleate are reported.

  呋喃和马来酸的反应在几种溶剂中进行。的内切-adduct分离并通过它的光谱特性确定的结构和转换成已知的化合物。报道了呋喃与富马酸，富马酸二乙酯和马来酸二乙酯的加合物。
• Desymmetric Hydrogenation of meso-Dicarboxylic Acids
  作者：Lei Yang、Tilong Yang、Yu Qian、Xumu Zhang、Jialin Wen

  DOI：10.1021/jacs.4c02538

  日期：2024.6.12

  reduction of abundant carboxylic acids with molecular hydrogen has been of both practical and theoretical value. We herein report the homogeneous hydrogenation of dicarboxylic acids with the strategy of desymmetrization. Using a rhodium/bisphosphine catalyst, one carboxyl group of meso-diacids was selectively reduced to yield chiral lactones with satisfactory enantioselectivity. This method provides a straightforward

  将平台化学品有效转化为关键中间体对于制药行业来说变得越来越重要。用分子氢催化还原丰富的羧酸的发展具有实用和理论价值。我们在此报告了采用去对称化策略的二羧酸的均相氢化。使用铑/双膦催化剂，选择性还原内消旋二酸的一个羧基，生成具有令人满意的对映选择性的手性内酯。该方法提供了一种直接的方法来生产用于制造生物素、特拉匹韦和其他抗病毒药物的手性内酯中间体。进行了实验和计算研究，揭示了催化循环中一种新颖的邻基协调机制。
• Ion Conducting ROMP Monomers Based on (Oxa)norbornenes with Pendant Imidazolium Salts Connected via Oligo(oxyethylene) Units and with Oligo(ethyleneoxy) Terminal Moieties
  作者：Terry L. Price、U Hyeok Choi、Daniel V. Schoonover、Murugan Arunachalam、Renxuan Xie、Steven Lyle、Ralph H. Colby、Harry W. Gibson

  DOI：10.1021/acs.macromol.8b02295

  日期：2019.2.26

  A matrix of 22 two-armed norbornene-based imidazolium TFSI monomers (8) was synthesized to determine the optimal structure in terms of single ion conductivity. For the chain tethering the imidazolium ring to the norbornene ring three or four oxyethylene units are optimal. A terminal group of two ethyleneoxy units was optimal. NMR studies indicated that both the tether oxyethylene units and the terminal ethyleneoxy units interact with the imidazolium cation via hydrogen bonding. 8r (X = 4, Y = 2) exhibited a conductivity of 9.57 x 10(-5) S/cm at 25 degrees C and a T-g of -46 degrees C. Low T-g values do not correlate with higher conductivity as a result of the H-bonding interactions. Stability toward autopolymerization and reasonable conductivities provide an acceptable platform for ion conducting ROMP polymers. Four one-armed norbornene-based imidazolium TFSI monomers (15) were prepared with tetra(ethyleneoxy) linkers/spacers and variable terminal groups. All of these exhibited low T(g)s (<-55 degrees C) and room temperature conductivities >10(-4) S/cm, the highest being 4.39 X 10(-4) S/cm for 15c (T-g = -69 degrees C), the analogue of 8r, providing hope for outstanding polymers. Three oxanorbornene-based two-armed imidazolium TFSI monomers (18) were prepared with varied linkers and terminal groups. 18b possesses a room temperature conductivity of 1.2 X 10(-4) S/cm, again augering well for polymers derived therefrom by ROMP.