dioxocularine | 107602-50-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: dioxocularine
• 英文别名: 5,6,17-Trimethoxy-11-methyl-2-oxa-11-azatetracyclo[8.7.1.03,8.014,18]octadeca-1(17),3,5,7,9,14(18),15-heptaene-12,13-dione
• CAS: 107602-50-6
• 化学式: C₂₀H₁₇NO₆
• 分子量: 367.358
• InChiKey: MGLLESNRDOAWOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  枯拉定 在 硫酸 、 sodium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 溶剂黄146 、 苯 为溶剂， 反应 5.0h， 生成 dioxocularine
  参考文献：
  名称：

  Lera, Angel Rodriguez de; Villaverde, Carmen; Castedo, Luis, Heterocycles, 1986, vol. 24, # 8, p. 2219 - 2225

  摘要：

  DOI：

文献信息

• Total synthesis of cularine alkaloids via dibenzoxepines as key intermediates
  作者：Alberto Garcia、Luis Castedo、Domingo Domínguez

  DOI：10.1016/0040-4020(95)00473-l

  日期：1995.7

  The total synthesis of several cularine alkaloids (cularine, oxocularine, dioxocularine and 4-hydroxycularine) via 10,11-dihydrodibenz(b,f)oxepin-10-ones as key intermediates is reported.

  据报道，通过10,11-dihydrodibenz（b，f）oxepin-10-ones作为关键中间体，可以合成几种lenine生物碱（lenine，oxocularine，dioxocularine和4-hydroxyphthaline）。
• A versatile approach to the synthesis of 4,5-dioxoaporphine and 3,4-dioxocularine alkaloids. One-Pot sequential ring formation from arylacetamides
  作者：Rafael Suau、Juan Manuel López-Romero、Rodrigo Rico

  DOI：10.1016/s0040-4039(97)82963-2

  日期：1996.12

  Cyclization of biarylacetamides to their phenanthrene derivatives is promoted by oxalyl chloride/stannyl chloride. The reaction proceeds with a second cyclization in which the oxalyl fragment acts as an alpha-dicarbonyl transfer agent to give 4,5-dioxoaporphine alkaloids in a single step. This double cyclization was also applied to aryloxyphenyl acetamides to give the corresponding 3,4-dioxocularine alkaloids. Decarbonylated aristocularine alkaloids were also formed in this case. Copyright (C) 1996 Elsevier Science Ltd