1,2-二甲氧基-6-甲基-4H-二苯并[de,g]喹啉-4,5(6H)-二酮 | 55610-02-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 中文名称: 1,2-二甲氧基-6-甲基-4H-二苯并[de,g]喹啉-4,5(6H)-二酮
• 英文名称: cepharadione B
• 英文别名: cepharadione-B；1,2-dimethoxy-6-methyl-6H-dibenzo[de,g]quinoline-4,5-dione；15,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,8,13,15-heptaene-11,12-dione
• CAS: 55610-02-1
• 化学式: C₁₉H₁₅NO₄
• 分子量: 321.332
• InChiKey: AFKGBLKLNRDQFN-UHFFFAOYSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  267-268°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 储存条件：
  存储条件：密封、干燥、避光，适宜温度为2-8°C。

制备方法与用途

溶解于乙醇

反应信息

• 作为反应物：
  描述：

  1,2-二甲氧基-6-甲基-4H-二苯并[de,g]喹啉-4,5(6H)-二酮 在 硼烷四氢呋喃络合物 作用下， 反应 3.0h， 以79%的产率得到4-hydroxydehydronuciferine
  参考文献：
  名称：

  钯（0）铃木交叉偶联反应是合成阿片类药物的关键步骤

  摘要：

  我们报告了一种灵活的方法，可以基于钯（0）催化的苯硼酸与空间受阻的2-溴苯基乙酸酯或溴代苯基乙酰胺的铃木交叉偶联，对4,5-二氧杂卟啉进行全合成，然后依次进行二环化的联芳基乙酰胺由草酰氯/路易斯酸。4，5-二氧杂卟啉的还原提供了对磷腈，脱氢紫杉醇和4-羟基-脱氢紫杉醇的化学选择性进入。（±）为一个三步骤的总合成- ø，ö还报道从容易获得的前体'-dimethylapomorphine。

  DOI：

  10.1016/j.tet.2004.05.014
• 作为产物：
  描述：

  10-N-methylamino-3,4-dimethoxy phenanthrene 在 sodium hydroxide 、 air 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 1,2-二甲氧基-6-甲基-4H-二苯并[de,g]喹啉-4,5(6H)-二酮
  参考文献：
  名称：

  由预先形成的联芳基键前体合成4,5-二氧杂卟啉生物碱的新方法

  摘要：

  描述了头孢拉酮-B和2-脱甲氧基类似物的合成。由芴酮开始，在Bischler-Napieralsky条件下，环化（联苯-2-基）乙酰基吗啉形成环C。氯乙酰胺的光化学用于形成环B。评估了这些化合物对几种肿瘤细胞系的细胞毒性。

  DOI：

  10.1016/0040-4020(96)00657-6

文献信息

• Synthesis and biological evaluation of cepharadiones A and B and related dioxoaporphines
  作者：Mark A. Elban、Jean C. Chapuis、Mei Li、Sidney M. Hecht

  DOI：10.1016/j.bmc.2007.06.035

  日期：2007.9

  Described herein is the first total synthesis and structural confirmation of cepharadione A, a naturally occurring DNA damaging agent. Also reported is the synthesis of cepharadione B, a closely related natural product, as well as the biological evaluation of both natural products. Finally, the preparation and biological evaluation of novel dioxoaporphine analogues is described. (c) 2007 Elsevier Ltd. All rights reserved.
• New benzyne approach to the synthesis of dehydroaporphines, 4,5-dioxoaporphines and aristolactams
  作者：Luis Casteda、Enrique Guitián、José M. Saá、Rafael Suau

  DOI：10.1016/s0040-4039(00)86859-8

  日期：——
• Intermolecular benzyne cycloaddition (IBC) approach to aporphinoids. Total syntheses of norcepharadione B, cepharadione B, dehydroanonaine, duguenaine, dehydronornuciferine, pontevedrine, O-methylatheroline, lysicamine, and alkaloid PO-3
  作者：N. Atanes、L. Castedo、E. Guitian、C. Saa、J. M. Saa、R. Suau

  DOI：10.1021/jo00009a010

  日期：1991.4

  We describe a useful novel approach to the synthesis of aporphinoids, including dehydroaporphines, aristolactams, 4,5-dioxoaporphines, and 7-oxoaporphines, by means of intermolecular benzyne cycloaddition (IBC). Specifically, we report the total synthesis of the isoquinoline alkaloids norcepharadione B, cepharadione B, dehydroanonaine, duguenaine, dehydronornuciferine, pontevedrine, O-methylatheroline, lysicamine, and alkaloid PO-3.
• 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
• Sequential bicyclization of biphenyl acetamides promoted by (COCl)2/SnCl4. Total synthesis of 4,5-dioxoaporphines
  作者：Rafael Suau、Juan Manuel López-Romero、Rodrigo Rico

  DOI：10.1016/s0040-4020(97)00923-x

  日期：1997.10

  The reaction of biphenyl acetamides with excess of oxalyl chloride/stannyl chloride offers a one pot, high-yield entry to 4,5-dioxoaporphine alkaloids. This strategy has been applied to the synthesis of 4,5-dioxodehydrocorydine starting from 1-iodo-2,3-dimethoxybenzene. The cytotoxicity of tetraoxygenated 4,5-dioxoaporphines has been evaluated. (C) 1997 Elsevier Science Ltd.