6,7-bis(t-butyldimethylsilyloxy)-1,4-epoxy-1,4-dihydronaphthalene | 153185-83-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6,7-bis(t-butyldimethylsilyloxy)-1,4-epoxy-1,4-dihydronaphthalene
• 英文别名: Tert-butyl-[[5-[tert-butyl(dimethyl)silyl]oxy-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraen-4-yl]oxy]-dimethylsilane；tert-butyl-[[5-[tert-butyl(dimethyl)silyl]oxy-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraen-4-yl]oxy]-dimethylsilane
• CAS: 153185-83-2
• 化学式: C₂₂H₃₆O₃Si₂
• 分子量: 404.697
• InChiKey: JMFQAXJHXPSFIK-UHFFFAOYSA-N

物化性质

• 沸点：
  395.0±42.0 °C(predicted)
• 密度：
  1.001±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.14
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7-bis(t-butyldimethylsilyloxy)-1,4-epoxy-1,4-dihydronaphthalene 在 potassium fluoride 、 dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II) 、 锌 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 27.0h， 生成 3,4-dihydroxy-7,8-dimethoxy-6H-naphtho[1,2-b]benzo[d]pyran-6-one
  参考文献：
  名称：

  Nickel-Catalyzed Synthesis of Benzocoumarins:  Application to the Total Synthesis of Arnottin I

  摘要：

  The ring-opening addition of methyl 2,3-dimethoxy-6-iodobenzoate to oxabenzonorbornadienes followed by cyclization in the presence of NiBr2( dppe) and Zn metal powder in acetonitrile at 80 C to give the corresponding benzocoumarin derivatives is described. This methodology was then applied to the synthesis of natural product arnottin I, first isolated from Xanthoxylum arnottianum Maxim, using protecting group chemistry. After deprotection and subsequent ring closure, arnottin I was obtained in 21% overall yield after six steps starting from catechol.

  DOI：

  10.1021/jo061477h
• 作为产物：
  描述：

  O,O'-bis(tert-butyldimethylsilyl)catechol 在 正丁基锂 、 溴 、 碘 、 silver trifluoroacetate 、 thallium(III) acetate 作用下， 以 四氯化碳 、 乙醚 、 正己烷 、 氯仿 为溶剂， 生成 6,7-bis(t-butyldimethylsilyloxy)-1,4-epoxy-1,4-dihydronaphthalene
  参考文献：
  名称：

  Syntheses of oxygen bridged, rigid catecholamine analogues. Effects on adrenergic and dopaminergic systems

  摘要：

  A series of 2-amino-1,2,3,4-tetrahydro-1,4-epoxynaphthalenes were synthesized and tested for affinity for dopaminergic and alpha-adrenergic receptor subtypes via radioligand binding assays. The unsubstituted analogue 2a showed weak affinity for both D1 and alpha2-adrenoceptors. This compound exhibited subtype selectivity in both dopaminergic and alpha adrenergic systems. Analogue 5 showed affinity only for the D1-receptor. Most other analogues showed no affinity for either receptor at concentrations up to 10 muM. Functional studies showed compound 2a to be an alpha-adrenoceptor antagonist, and confirmed its alpha2-adrenoceptor selectivity predicted by the radioligand binding assay.

  DOI：

  10.1016/0223-5234(93)90141-z

文献信息

• Nickel-Catalyzed Synthesis of Benzocoumarins:  Application to the Total Synthesis of Arnottin I
  作者：Sachin Madan、Chien-Hong Cheng

  DOI：10.1021/jo061477h

  日期：2006.10.1

  The ring-opening addition of methyl 2,3-dimethoxy-6-iodobenzoate to oxabenzonorbornadienes followed by cyclization in the presence of NiBr2( dppe) and Zn metal powder in acetonitrile at 80 C to give the corresponding benzocoumarin derivatives is described. This methodology was then applied to the synthesis of natural product arnottin I, first isolated from Xanthoxylum arnottianum Maxim, using protecting group chemistry. After deprotection and subsequent ring closure, arnottin I was obtained in 21% overall yield after six steps starting from catechol.
• Syntheses of oxygen bridged, rigid catecholamine analogues. Effects on adrenergic and dopaminergic systems
  作者：A Kouvarakis、K Thermos、JP Hieble、HE Katerinopoulos

  DOI：10.1016/0223-5234(93)90141-z

  日期：1993.1

  A series of 2-amino-1,2,3,4-tetrahydro-1,4-epoxynaphthalenes were synthesized and tested for affinity for dopaminergic and alpha-adrenergic receptor subtypes via radioligand binding assays. The unsubstituted analogue 2a showed weak affinity for both D1 and alpha2-adrenoceptors. This compound exhibited subtype selectivity in both dopaminergic and alpha adrenergic systems. Analogue 5 showed affinity only for the D1-receptor. Most other analogues showed no affinity for either receptor at concentrations up to 10 muM. Functional studies showed compound 2a to be an alpha-adrenoceptor antagonist, and confirmed its alpha2-adrenoceptor selectivity predicted by the radioligand binding assay.