6,7-dimethoxy-8-[4-(triisopropylsilanyloxy)phenyl]isochroman-1-one | 478910-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6,7-dimethoxy-8-[4-(triisopropylsilanyloxy)phenyl]isochroman-1-one
• CAS: 478910-85-9
• 化学式: C₂₆H₃₆O₅Si
• 分子量: 456.654
• InChiKey: MHNBWTQNGMSFHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.64
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-8-[4-(triisopropylsilanyloxy)phenyl]isochroman-1-one 在 咪唑 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 正丁基锂 、 4 A molecular sieve 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 5-[2-(tert-butyldimethylsilanyloxy)ethyl]-6-ethynyl-2,3-dimethoxy-4'-(triisopropylsilanyloxy)biphenyl
  参考文献：
  名称：

  Total Synthesis of the Tropoloisoquinoline Alkaloid Pareitropone via Alkynyliodonium Salt Chemistry and Related Studies

  摘要：

  The first chemical synthesis of pareitropone, by a route featuring application of alkynyliodonium salt chemistry, is described. The key transform initiates with addition of an alkylidenecarbene, derived by intramolecular nucleophile addition to the alkynyliodonium moiety, to a proximal aromatic ring. This addition delivers a highly strained norcaradiene substructure that rapidly reorganizes to furnish the pareitropone skeleton.

  DOI：

  10.1021/jo026337w
• 作为产物：
  描述：

  4,4-dimethyl-2-(2,3,4-trimethoxyphenyl)-4,5-oxazoline 在 盐酸 、 正丁基锂 、 异丙基氯化镁 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 35.0h， 生成 6,7-dimethoxy-8-[4-(triisopropylsilanyloxy)phenyl]isochroman-1-one
  参考文献：
  名称：

  Total Synthesis of the Tropoloisoquinoline Alkaloid Pareitropone via Alkynyliodonium Salt Chemistry and Related Studies

  摘要：

  The first chemical synthesis of pareitropone, by a route featuring application of alkynyliodonium salt chemistry, is described. The key transform initiates with addition of an alkylidenecarbene, derived by intramolecular nucleophile addition to the alkynyliodonium moiety, to a proximal aromatic ring. This addition delivers a highly strained norcaradiene substructure that rapidly reorganizes to furnish the pareitropone skeleton.

  DOI：

  10.1021/jo026337w

文献信息

• Alkynyliodonium Salts in Organic Synthesis. Application to the Total Synthesis of the Tropoloisoquinoline Alkaloid Pareitropone
  作者：Ken S. Feldman、Timothy D. Cutarelli

  DOI：10.1021/ja0277430

  日期：2002.10.1

  The synthesis of the tropoloisoquinoline alkaloid pareitropone has been accomplished in 14 steps from 2,3,4-trimethoxybenzoic acid. The key transformations include the generation of an alkylidenecarbene intermediate through intramolecular addition of a tosylamide anion to an alkynyliodonium salt, and the cycloaddition of that carbene to a peri positioned aromatic ring to afford a cycloheptatrienylidene product featuring the intact pareitropone skeleton.