7-oxabicyclo[2.2.1]hept-5-en-2-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-ylmethanol
• 英文别名: (1RS,2SR,4RS)-7-oxabicyclo[2.2.1]hept-5-ene-2-methanol；[(1S,2R,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-QYNIQEEDSA-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-ylmethanol 在 吡啶 、 四氧化锇 、 苄基三乙基氯化铵 作用下， 以 氯仿 、 水 、 叔丁醇 为溶剂， 反应 72.0h， 生成 (+/-)-3-exo-Acetoxy-5-endo-acetoxymethyl-2-exo-p-toluenesulfonamido-7-oxabicyclo<2.2.1>heptane
  参考文献：
  名称：

  Ogawa, Seiichiro; Tsunoda, Hidetoshi; Yoshikawa, Masaru, Liebigs Annalen der Chemie, 1992, # 6, p. 629 - 636

  摘要：

  DOI：
• 作为产物：
  描述：

  7-oxabicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 5.0h， 以100%的产率得到7-oxabicyclo[2.2.1]hept-5-en-2-ylmethanol
  参考文献：
  名称：

  Diels-Alder 呋喃加合物的合成研究。(±)-Avenaciolide 的正式全合成

  摘要：

  呋喃与丙烯酸甲酯的内切-狄尔斯-阿尔德加合物转化为双-γ-内酯衍生物，这是合成 (±)-avenaciolide 的众所周知的前体。该路线包括13步，总收率为17.9%。

  DOI：

  10.1246/bcsj.59.3881

文献信息

• COMPOUNDS AND USES THEREOF FOR THE MODULATION OF HEMOGLOBIN
  申请人：Global Blood Therapeutics, Inc.

  公开号：US20150141465A1

  公开（公告）日：2015-05-21

  Provide herein are compounds and pharmaceutical compositions suitable as modulators of hemoglobin, methods and intermediates for their preparation, and methods for their use in treating disorders mediated by hemoglobin and disorders that would benefit from tissue and/or cellular oxygenation.

  本文提供了适用作为血红蛋白调节剂的化合物和药物组合物，它们的制备方法和中间体，以及在治疗由血红蛋白介导的疾病和需要组织和/或细胞氧合的疾病中使用它们的方法。
• 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。
• Synthetic Studies of Diels–Alder Adduct of Furan. Formal Total Synthesis of (±)-Avenaciolide
  作者：Hiyoshizo Kotsuki、Hiroyuki Ohnishi、Yasuhiro Akitomo、Masamitsu Ochi

  DOI：10.1246/bcsj.59.3881

  日期：1986.12

  The endo-Diels–Alder adduct of furan with methyl acrylate was transformed into a bis-γ-lactone derivative which is a well-known precursor for the synthesis of (±)-avenaciolide. The route involves 13 steps and the overall yield was 17.9%.

  呋喃与丙烯酸甲酯的内切-狄尔斯-阿尔德加合物转化为双-γ-内酯衍生物，这是合成 (±)-avenaciolide 的众所周知的前体。该路线包括13步，总收率为17.9%。