6,7-dimethoxy-8-(4-methoxyphenyl)isochroman-1-one | 478910-77-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6,7-dimethoxy-8-(4-methoxyphenyl)isochroman-1-one
• 英文别名: 6,7-Dimethoxy-8-(4-methoxyphenyl)-3,4-dihydroisochromen-1-one
• CAS: 478910-77-9
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: ICULATMPRQWVCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-8-(4-methoxyphenyl)isochroman-1-one 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以100%的产率得到2-[2-(Hydroxymethyl)-4,5-dimethoxy-3-(4-methoxyphenyl)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-<2-(4-methoxyphenyl)-3,4-dimethoxyphenyl>-4,4-dimethyl-2-oxazoline 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.33h， 生成 6,7-dimethoxy-8-(4-methoxyphenyl)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

• 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.