[6-[2-[Tert-butyl(diphenyl)silyl]oxyethyl]-3,4-dimethoxy-2-(4-methoxyphenyl)phenyl]methanol | 478910-90-6

• 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: [6-[2-[Tert-butyl(diphenyl)silyl]oxyethyl]-3,4-dimethoxy-2-(4-methoxyphenyl)phenyl]methanol
• CAS: 478910-90-6
• 化学式: C₃₄H₄₀O₅Si
• 分子量: 556.774
• InChiKey: FDUDUKJJHPUVKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.99
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [6-[2-[Tert-butyl(diphenyl)silyl]oxyethyl]-3,4-dimethoxy-2-(4-methoxyphenyl)phenyl]methanol 在 重铬酸吡啶 、 正丁基锂 、 4 A molecular sieve 、 四丁基氟化铵 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-(2-ethynyl-5,6,4'-trimethoxybiphenyl-3-yl)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-<2-(4-methoxyphenyl)-3,4-dimethoxyphenyl>-4,4-dimethyl-2-oxazoline 在 咪唑 、 盐酸 、 正丁基锂 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.66h， 生成 [6-[2-[Tert-butyl(diphenyl)silyl]oxyethyl]-3,4-dimethoxy-2-(4-methoxyphenyl)phenyl]methanol
  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

• Total Synthesis of the Tropoloisoquinoline Alkaloid Pareitropone via Alkynyliodonium Salt Chemistry and Related Studies
  作者：Ken S. Feldman、Timothy D. Cutarelli、Romina Di Florio

  DOI：10.1021/jo026337w

  日期：2002.11.1

  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.