7-oxabicyclo<2.2.1>hept-5-en-2-exo-ylmethanol | 89898-05-5

• 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-exo-ylmethanol
• 英文别名: (1RS,2RS,4RS)-7-oxabicyclo[2.2.1]hept-5-ene-2-methanol；exo-7-oxabicyclo[2.2.1]hept-5-ene-2-methanol；7-oxabicyclo[2.2.1]hept-5-en-2-exo-ylmethanol；rac-[(1R,2R,4R)-7-oxabicyclo[2.2.1]hept-5-en-2-yl]methanol；[(1S,2S,4S)-7-oxabicyclo[2.2.1]hept-5-en-2-yl]methanol
• CAS: 89898-05-5；111080-27-4；112348-74-0；112348-87-5；133147-32-7
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: FUCCKJSLKAHDNQ-XVMARJQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-oxabicyclo<2.2.1>hept-5-en-2-exo-ylmethanol 在 sodium hydride 、 potassium carbonate 作用下， 以 氯仿 为溶剂， 反应 0.08h， 生成 2-exo-benzyloxymethyl-6-endo-bromo-5-exo-phenylselenyl-7-oxabicyclo<2.2.1>heptane
  参考文献：
  名称：

  Regioselective electrophilic additions to 2-alkoxy- and 2-alkoxymethyl-7-oxabicyclo [2.2.1] hept-5-ene derivatives

  摘要：

  DOI：

  10.1016/s0040-4020(01)81476-9
• 作为产物：
  描述：

  exo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以61%的产率得到7-oxabicyclo<2.2.1>hept-5-en-2-exo-ylmethanol
  参考文献：
  名称：

  Norbornenes in Inverse Electron-Demand Diels-Alder Reactions

  摘要：

  Significant differences in the reactivity of norbornene derivatives in the inverse electron-demand Diels-Alder reaction with tetrazines were revealed by kinetic studies. Substantial rate enhancement for the exo norbornene isomers was observed. Quantum-chemical calculations were used to rationalize and support the observed experimental data.

  DOI：

  10.1002/chem.201301838

文献信息

• Organocatalytic Asymmetric Diels-Alder Reaction of Furan under High Pressure
  作者：Hiyoshizo Kotsuki、Keiji Nakano、Yoshiyasu Ichikawa

  DOI：10.3987/com-09-s(s)85

  日期：——

  A new method for the asymmetric Diels-Alder reaction between furan and acrolein has been developed through the combined use of chiral organocatalysts and high pressure (yield up to 91%; endo-adduct up to 19% ee, exo-adduct up to 26% ee).

  通过结合使用手性有机催化剂和高压，开发了一种呋喃和丙烯醛之间的不对称 Diels-Alder 反应的新方法（产率高达 91%；内加合物高达 19% ee，外加合物高达 26% ee)。
• Synthesis of novel carbocyclic nucleoside analogues derived from 7-oxabicyclo[2.2.1]heptane-2-methanol
  作者：Hubert Hřebabecký、Martin Dračínský、Armando M. De Palma、Johan Neyts、Antonín Holý

  DOI：10.1135/cccc2008204

  日期：——

  Hydroboration of [(1R*,2R*,4R*)-7-oxabicyclo[2.2.1]hept-5-en-2-yl]methyl benzoate (5), which was prepared by Diels–Alder reaction of furan with acrolein and subsequent reduction and benzoylation of the Diels–Alder product, afforded [(1R*,2S*,4S*,6S*)-6-hydroxy-7-oxabicyclo[2.2.1]heptan-2-yl]methyl benzoate (6) and [(1R*,2R*,4R*,5S*)-5-hydroxy-7-oxabicyclo[2.2.1]heptan-2-yl]methyl benzoate (7). The key intermediates, [(1R*,2S*,4S*,6R*)-6-hydroxy-7-oxabicyclo[2.2.1]heptan-2-yl]methyl benzoate (10) and [(1R*,2R*,4R*,5R*)-5-hydroxy-7-oxabicyclo[2.2.1]heptan-2-yl]methyl benzoate (11), were prepared from6and7, respectively, by oxidation with pyridinium dichromate and subsequent reduction of the thus obtained ketones. The Mitsunobu reaction of10and11with 6-chloropurine and subsequent reductive deprotection with diisobutylaluminium hydride afforded 6-chloropurine derivatives, which were converted to other purine analogues. Thymine analogues were prepared by Mitsunobu reaction of10and11with 3-benzoyl-5-methylpyrimidine-2,4(1H,3H)-dione and subsequent methanolysis. The target compounds were tested for the activity againstCoxsackievirus.

  将[(1R*,2R*,4R*)-7-氧杂双环[2.2.1]庚-5-烯-2-基]甲基苯甲酸酯（5），通过呋喃与丙烯醛的Diels-Alder反应制备，随后还原和苯甲酰化Diels-Alder产物，进行氢硼化反应，得到[(1R*,2S*,4S*,6S*)-6-羟基-7-氧杂双环[2.2.1]庚-2-基]甲基苯甲酸酯（6）和[(1R*,2R*,4R*,5S*)-5-羟基-7-氧杂双环[2.2.1]庚-2-基]甲基苯甲酸酯（7）。关键中间体[(1R*,2S*,4S*,6R*)-6-羟基-7-氧杂双环[2.2.1]庚-2-基]甲基苯甲酸酯（10）和[(1R*,2R*,4R*,5R*)-5-羟基-7-氧杂双环[2.2.1]庚-2-基]甲基苯甲酸酯（11），分别通过吡啶二铬酸盐氧化和随后还原所得酮制备自6和7。将10和11与6-氯嘌呤进行Mitsunobu反应，随后用二异丁基铝氢化物进行还原去保护作用，得到6-氯嘌呤衍生物，可转化为其他嘌呤类似物。通过10和11与3-苯甲酰-5-甲基嘧啶-2,4(1H,3H)-二酮进行Mitsunobu反应，随后进行甲醇解，制备嘧啶类似物。对目标化合物进行了对柯萨奇病毒活性的测试。
• Ring-opening Sn2' reactions of 7-oxanorbornenes by organolithium reagents. Regio- and stereospecific synthesis of substituted cyclohexenediols
  作者：Odón Arjona、Roberto Fernández de la Pradilla、Angel Martin-Domenech、Joaquin Plumet

  DOI：10.1016/s0040-4020(01)81475-7

  日期：——

  The nucleophilic Sn2' bridge opening of 7-oxabicyclo[2.2.1] hept-5-en-2-ols with organolithium reagents occurs in a regio- and stereospecific fashion to produce 6-substituted-cyclohex-4-en-1,3-diols, regardless of the stereochemistry at C-2. A free alcohol functionality is necessary to attain complete regiocontrol of the process. The methodology is utilized to prepare an optically pure cyclohexene

  7-氧杂双环[2.2.1]庚-5-烯-2-醇与有机锂试剂的亲核Sn2'桥开口以区域和立体特异性方式发生，以产生6-取代的环己-4-烯-1,3 -二醇，无论在C-2处的立体化学如何。要完全控制该过程，必须使用游离的醇功能。该方法用于制备光学纯的环己烯衍生物（+）-（1S，3S，6R）-6-正丁基-3-甲基-环己-4-en-1,3-二醇（5b），模型系统。
• Synthesis of pseudo-sugar derivatives from 5exo, 6exo-dihydroxy-endo- and -exo-7-oxabicyclo[2.2.1]heptane-2-carboxylic acids
  作者：Seiichiro Ogawa、Masaki Uemura、Toichi Fujita

  DOI：10.1016/0008-6215(88)85054-7

  日期：1988.6

  L'acetolyse et la bromation de certains derives de l'acide dihydroxy-5 exo,6exo endo- et exo-oxa-7 bicyclo [2.2.1] heptanecarboxylique-2 fournit des pseudo-sucres

  L'acetolyse等人肯定地衍生了l'acide dihydroxy-5 exo，6exo endo- et exo-oxa-7 bicyclo [2.2.1]庚烷羧基2 Fournit des假糖
• Method for Preparing Curable Bicyclic Compound Derived from Biomass
  申请人：Korea Institute of Industrial Technology

  公开号：US20140066637A1

  公开（公告）日：2014-03-06

  The present invention relates to a curable bicyclic compound derived from biomass, solvent-free curable composition and a method for preparing thereof. The curable compound derived from biomass according to the invention comprises a bicycle structure, to which one of two epoxide functional groups are bonded.

  本发明涉及一种来自生物质的可固化的双环化合物，无溶剂可固化组合物以及其制备方法。根据本发明，来自生物质的可固化化合物包括一个双环结构，其中一个或两个环氧基团之一与之结合。