2,3-bis(tert-butyldimethylsilyloxy)-7,8-dimethoxy-6H-dibenzo[c,h]chromen-6-one | 914300-24-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2,3-bis(tert-butyldimethylsilyloxy)-7,8-dimethoxy-6H-dibenzo[c,h]chromen-6-one
• 英文别名: 2,3-Bis[[tert-butyl(dimethyl)silyl]oxy]-7,8-dimethoxynaphtho[1,2-c]isochromen-6-one
• CAS: 914300-24-6
• 化学式: C₃₁H₄₂O₆Si₂
• 分子量: 566.842
• InChiKey: ZUUOGXMFBAXTFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.88
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-bis(tert-butyldimethylsilyloxy)-7,8-dimethoxy-6H-dibenzo[c,h]chromen-6-one 在 potassium fluoride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 15.0h， 以90%的产率得到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：

  1,2-dibromo-4,5-bis(tert-butyldimethylsilyloxy)benzene 在 正丁基锂 、 dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II) 、 锌 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 12.0h， 生成 2,3-bis(tert-butyldimethylsilyloxy)-7,8-dimethoxy-6H-dibenzo[c,h]chromen-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

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.