2-[2-(Hydroxymethyl)-4,5-dimethoxy-3-[4-tri(propan-2-yl)silyloxyphenyl]phenyl]ethanol | 473840-68-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[2-(Hydroxymethyl)-4,5-dimethoxy-3-[4-tri(propan-2-yl)silyloxyphenyl]phenyl]ethanol
• CAS: 473840-68-5
• 化学式: C₂₆H₄₀O₅Si
• 分子量: 460.686
• InChiKey: LGVPMWMGUNMSHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[2-(Hydroxymethyl)-4,5-dimethoxy-3-[4-tri(propan-2-yl)silyloxyphenyl]phenyl]ethanol 在 咪唑 、 重铬酸吡啶 、 正丁基锂 、 4 A molecular sieve 、 氢氟酸 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 22.0h， 生成 2-[2-Ethynyl-4,5-dimethoxy-3-[4-tri(propan-2-yl)silyloxyphenyl]phenyl]ethanol
  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：

  2-[5,6-dimethoxy-4'-(triisopropylsilanyloxy)biphenyl-2-yl]-4,4-dimethyl-4,5-dihydrooxazole 在 盐酸 、 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 20.0h， 生成 2-[2-(Hydroxymethyl)-4,5-dimethoxy-3-[4-tri(propan-2-yl)silyloxyphenyl]phenyl]ethanol
  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.