(1α,4α)-1,2,3,4-tetrahydro-1,4-epoxynaphthalen-2α-ol | 96898-07-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (1α,4α)-1,2,3,4-tetrahydro-1,4-epoxynaphthalen-2α-ol
• 英文别名: exo-2-hydroxy-1,2,3,4-tetrahydro-1,4-epoxynaphthalene；7-oxo-exo-2-benznorborneol；(1S,8S,9R)-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6-trien-9-ol
• CAS: 96898-07-6
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: FEFHDGOVLKCADH-UTLUCORTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (1α,4α)-1,2,3,4-tetrahydro-1,4-epoxynaphthalen-2α-ol 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以74%的产率得到2-oxo-1,2,3,4-tetrahydro-1,4-epoxynaphthalene
  参考文献：
  名称：

  2-Amino- and 2-guanidino-1,2,3,4-tetrahydro-1,4-epoxynaphthalenes as conformationally defined analogs of .alpha.-adrenergic agents

  摘要：

  The exo- and endo-2-amino-5,8-dimethoxy-1,2,3,4-tetrahydro-1,4-epoxynaphthalenes++ + (3b and 4b, respectively) were prepared and evaluated as conformationally defined analogues of the alpha 1-agonist methoxamine. Only compound 3b exhibited significant alpha 1-agonist activity in the field stimulated rat vas deferens assay. Since 3b closely approximates the antiperiplanar form of (1R,2S)-(-)-erythro-methoxamine, the results suggest that methoxamine interacts with the alpha 1-adrenoceptor in the trans extended form. The exo-guanidino derivative 5 was found to be a partial alpha 1-agonist. Among the exo- and endo-2-amino-1,2,3,4-tetrahydro-1,4-epoxynaphthalenes (3a and 4a, respectively) prepared as rigid analogues of norephedrine, compound 3a possessed agonist activity at both alpha 1- and alpha 2-adrenoceptors, whereas 4a was inactive at either receptor.

  DOI：

  10.1021/jm00389a023
• 作为产物：
  描述：

  对甲苯磺酸2-溴苯酯 在 lithium aluminium tetrahydride 、 正丁基锂 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 水 为溶剂， 反应 6.5h， 生成 (1α,4α)-1,2,3,4-tetrahydro-1,4-epoxynaphthalen-2α-ol
  参考文献：
  名称：

  Baker, Robert W.; Baker, Teresa M. (nee Nicoletti); Birkbeck, Anthony A., Journal of the Chemical Society. Perkin transactions I, 1991, # 6, p. 1589 - 1600

  摘要：

  DOI：

文献信息

• Chiral synthesis via organoboranes. 6. Hydroboration. 74. Asymmetric hydroboration of representative heterocyclic olefins with diisopinocampheylborane. Synthesis of heterocyclic boronates and heterocyclic alcohols of very high enantiomeric purity
  作者：Herbert C. Brown、J. V. N. Vara. Prasad

  DOI：10.1021/ja00268a053

  日期：1986.4

  Etude de la borhydratation de dihydrofurannes, -thiophenes, -pyrannes et -thiopyrannes et de pyrrolines et tetrahydropyridines: obtention des heterocycles perhydrogenes correspondants hydroxyles et diethoxyboryles en 3; reactions de ces derniers avec la diethanolamine et obtention d'amine-boranes internes derives d'heteryl-2 perhydro dioxazaborocines-1,3,6,2

  Etude de la borhydratation de dihydrofuranes, -thiophenes, -pyrannes et -thiopyranes et de pyrrolines et de tetrahydropyridines: obtention des杂环全氢对应物羟基和二乙氧基硼烯 3; 反应 de ces de derniers avec la diethanolamine et obtention d'amine-boranes internes 衍生 d'heteryl-2 perhydro dioxazaborocines-1,3,6,2
• Hydroboration. 83. Asymmetric hydroboration of representative cis disubstituted and heterocyclic olefins with dicaranylboranes of high enantiomeric purity
  作者：Herbert C. Brown、J. V. N. Vara Prasad、Marek Zaidlewicz

  DOI：10.1021/jo00248a004

  日期：1988.6
• Hydroboration. 72. Hydroboration-oxidation of 1,4-epoxy-1,4-dihydronaphthalene with and without ring opening
  作者：Herbert C. Brown、J. V. N. Vara Prasad

  DOI：10.1021/jo00216a041

  日期：1985.8
• Copper(I)–Taniaphos Catalyzed Enantiodivergent Hydroboration of Bicyclic Alkenes
  作者：Hyesu Lee、Byoung Yoon Lee、Jaesook Yun

  DOI：10.1021/ol503598w

  日期：2015.2.6

  In this study, highly enantioselective copper(I)-catalyzed hydroboration of bicyclic alkenes is reported. Using a copper-taniaphos complex, excellent enantioselectivities up to >99% ee were obtained for bicyclic alkenes including oxa- and azabicyclic alkenes. Furthermore, copper-catalyzed enantiodivergent hydroboration methods with the same chiral ligand-copper precursors were developed using different boron sources based on alternative mechanistic pathways.