5,6-dihydro-8H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-one | 74133-23-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 5,6-dihydro-8H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-one
• 英文别名: 5,6-dihydro-2,3-methylenedioxy-8H-dibenzo[a,g]quinolizin-8-one；5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-one；2,3-methylenedioxy-8-oxoprotoberberine；13,14-didehydrogusanlung D；dehydrogusanlung D；5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-one；5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,15,17,19-heptaen-14-one
• CAS: 74133-23-6
• 化学式: C₁₈H₁₃NO₃
• 分子量: 291.306
• InChiKey: LZZLAQOWLGILET-UHFFFAOYSA-N

物化性质

• 熔点：
  181-182 °C
• 沸点：
  539.6±50.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6-dihydro-8H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-one 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 以61%的产率得到5,6,13,13a-tetrahydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-one
  参考文献：
  名称：

  Total synthesis of (±)-gusanlung D

  摘要：

  A new approach to the core structure of protoberberine alkaloid was described. Total synthesis of (+/-)-gusanlung D (2) was reported. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.119
• 作为产物：
  描述：

  邻碘苯甲酰氯 在 palladium diacetate 、 四乙基氯化铵 、 焦磷酸硫胺素 potassium carbonate 、 三乙胺 作用下， 以 乙腈 、 苯 为溶剂， 反应 14.0h， 生成 5,6-dihydro-8H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-one
  参考文献：
  名称：

  通过区域特异性分子内Heck反应合成稠环氮杂环

  摘要：

  一系列钯（在某些情况下为铑）催化的芳基碘化物和乙烯基溴化物在邻烯烃或杂芳环（吲哚，吡咯）上的区域特异性5-外-，6-内-和6-外-trig环化反应，导致宽各种稠环系统。在适当的情况下，该方法为创建四取代的碳中心提供了一种简便的方法。仅在少数情况下观察到产物中的双键异构化。

  DOI：

  10.1016/s0040-4020(01)90535-6

文献信息

• Protoberberines from Reissert-Compounds VIII [1]. Oxazoloisoquinolines, New and Efficient Educts for the Synthesis of 8-Oxoprotoberberines
  作者：Eberhard Reimann、Fritz Grasberger、Kurt Polborn

  DOI：10.1007/s00706-003-0013-5

  日期：2003.6

   Certain benzylated oxazoloisoquinolinones readily available from Reissert compounds provided an efficient access to 8-oxoprotoberberines in three steps. A series of these new precursors as well as several oxoprotoberberines were prepared and the scope and limitation of this procedure were investigated.

  可从 Reissert 化合物轻松获得的某些苄基恶唑基异喹啉酮可通过 三个步骤有效地获得8-氧代小pro碱。制备了一系列这些新的前体以及几种氧代小ber碱，并研究了该方法的范围和局限性。
• A convenient synthesis of 8-oxoprotoberberine derivatives
  作者：Somsak Ruchirawat、Werawat Lertwanawatana、Pongtip Thepchumrune

  DOI：10.1016/s0040-4039(00)71410-9

  日期：1980.1

  The annulation of isoquinoline derivatives to form the 8-oxoprotoberberine derivatives is described. The key step of the reaction involves intramolecular alkylation of the Reissert compounds.

  描述了异喹啉衍生物的环化以形成8-氧代小ber碱衍生物。反应的关键步骤涉及Reissert化合物的分子内烷基化。
• Synthesis of 8-oxoprotoberberines using acid-mediated cyclization or the Heck reaction
  作者：Anfeng Chen、Kun Zhao、Hankun Zhang、Xianwen Gan、Min Lei、Lihong Hu

  DOI：10.1007/s00706-011-0656-6

  日期：2012.5

  8-oxoprotoberberines is described from 6-benzoyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline-5-carbaldehyde via acid-mediated cyclization or from 2-(2-iodophenethyl)isoquinolin-1(2H)-one via the Heck reaction. The present method offers several advantages, such as good yields and a simple procedure. Graphical abstract

  摘要描述了一种由6-苯甲酰基-5,6,7,8-四氢-[1,3]二氧杂环戊[4,5 - g ]异喹啉-5-甲醛通过酸介导的环化合成8-氧代小ber碱的简便方法。通过Heck反应的2-（2-碘苯乙基）异喹啉-1（2H）-一。本方法具有许多优点，例如产率高和操作简单。 图形概要
• Synthesis of the Reported Protoberberine Gusanlung D
  作者：Narshinha Argade、Prasad Wakchaure、Srinivasan Easwar

  DOI：10.1055/s-0028-1088050

  日期：2009.5

  Starting from homopiperonylamine or phenethylamine with homophthalic anhydride or 3,4-methylenedioxyhomophthalic acid, respectively, facile syntheses of the reported structures of (±)-gusanlung D and (±)-isogusanlung D were accomplished via regioselective­ reductive dehydration of the corresponding homophthalimides followed by an intramolecular acid-catalyzed or radical cyclization pathway. Starting from the corresponding suitably ortho-halogenated homophthalimides, the syntheses of dehydrogusanlung and dehydroisogusanlung D were completed via regioselective reductive dehydration followed by an intramolecular Heck coupling reaction as the key steps. The analytical and spectral data obtained for all four synthetic compounds differed from the reported data for natural gusanlung D, and therefore the structural assignment of the natural product needs to be revised.

  分别从均哌酰基胺或苯乙胺与均苯二甲酸酐或 3,4-亚甲二氧基均苯二甲酸开始，通过相应均苯二甲酰亚胺的回归选择性还原脱水，然后通过分子内酸催化或自由基环化途径，轻松合成了所报道的 (±)-gusanlung D 和 (±)-isogusanlung D 结构。从相应的正交卤代均苯二甲酰亚胺开始，通过选择性还原脱水，然后以分子内 Heck 偶联反应为关键步骤，完成了脱氢古生隆和脱氢异古生隆 D 的合成。所有四种合成化合物的分析和光谱数据都与天然草珊瑚龙 D 的报告数据不同，因此需要对天然产物的结构分配进行修订。
• Total Syntheses of (±)-Gusanlung A, (±)-Gusanlung D and 8-Oxyberberrubine and the Uncertainty Concerning the Structures of (-)-Gusanlung A, (-)-Gusanlung D and 8-Oxyberberrubine
  作者：Surachai Nimgirawath、Phansuang Udomputtimekakul、Thitima Apornpisarn、Asawin Wanbanjob、Thongchai Taechowisan

  DOI：10.3390/molecules14020726

  日期：——

  (±)-Gusanlung A, 8-oxyberberrubine and (±)-gusanlung D have been synthesized by radical cyclisation of the corresponding 2-aroyl-1-methylenetetra- hydroisoquinolines. The 1H and 13C spectra of (-)-gusanlung D were found to be different from those of synthetic (±)-gusanlung D. Careful analyses of the 13C spectra of (–)-gusanlung A and natural 8-oxyberberrubine also cast doubt on the correctness of the structures previously assigned to these two compounds. (±)-Gusanlung A and (±)-gusanlung D were inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028.

  (±)-Gusanlung A、8-oxyberberrubine 和 (±)-gusanlung D 是通过相应的 2-芳酰基-1-亚甲基四氢异喹啉的自由基环化合成的。对 (-)-gusanlung A 和天然 8-oxyberberrubine 的 13C 光谱进行仔细分析后，发现 (-)-gusanlung D 的 1H 和 13C 光谱与合成 (±)-gusanlung D 的光谱不同。(±)-Gusanlung A 和 (±)-Gusanlung D 对金黄色葡萄球菌 ATCC25932、大肠杆菌 ATCC10536 和白色念珠菌 ATCC90028 均无活性。