8,9-bis(methyloxy)-2,3,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-5(1H)-one | 104058-44-8

• 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: 8,9-bis(methyloxy)-2,3,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-5(1H)-one
• 英文别名: 8,9-dimethoxy-1,2,3,10b-tetrahydropyrrolo[2,1-a]isoquinolin-5(6H)-one；8,9-dimethoxy-2,3,6,10b-tetrahydro-1H-pyrrolo[2,1-a]isoquinolin-5-one；8,9-dimethoxy-2,3,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-5(1H)-one；3,4-dimethoxyphenyl indolizinone
• CAS: 104058-44-8
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: SWFPPGOVUZNKEG-UHFFFAOYSA-N

物化性质

• 熔点：
  164-165 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  417.4±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  8,9-bis(methyloxy)-2,3,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-5(1H)-one 在 lithium aluminium tetrahydride 作用下， 生成 (+/-)-crispine A
  参考文献：
  名称：

  通过亚硝基烯烃杂-Diels-Alder加成至乙基乙烯基醚的合成（±）-Crispine A

  摘要：

  使用亚乙基烯烃杂-Diels-Alder加成乙基乙烯基醚作为关键步骤，可分9个步骤合成（±）-crispine A，总产率为24％。合成从商业3,4-二甲氧基苯基乙酸开始，并使用简单的方法，易于获得的材料和廉价的试剂。试图还原二氢-4 H -1,2-恶嗪中间体时，出乎意料地形成了异色满衍生物。 生物碱-天然产物-全合成-杂Diels-Alder反应-氢化

  DOI：

  10.1055/s-0030-1258333
• 作为产物：
  描述：

  (3,4-二甲氧基苯基)乙酰氯 生成 8,9-bis(methyloxy)-2,3,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-5(1H)-one
  参考文献：
  名称：

  Kano, Shinzo; Yuasa, Yoko; Shibuya, Shiroshi, Synthetic Communications, 1985, vol. 15, # 10, p. 883 - 890

  摘要：

  DOI：

文献信息

• A cascade approach to fused indolizinones through Lewis acid–copper(i) relay catalysis
  作者：Huawen Huang、Xiaochen Ji、Wanqing Wu、Huanfeng Jiang

  DOI：10.1039/c3cc40643a

  日期：——

  A relay catalytic cascade process involving Lewis acid triggered ring-opening of cyclopropyl ketones with nitriles, the copper(I)-catalyzed Ritter process, and acid-promoted N-acyliminium ion cyclization is described, which efficiently provides thieno-, furano-, and benzo-indolizinones in moderate to good yields.

  报道了一种涉及路易斯酸引发的环丙基酮与腈的环展开反应、铜(I)催化的Ritter反应以及酸促进的N-酰基亚胺离子环化的接力式催化级联过程，该过程能以中等至良好的产率高效合成噻吩并、呋喃并和苯并引朵嗪酮类化合物。
• An investigation into the electrophilic cyclisation of N-acyl-pyrrolidinium ions: a facile synthesis of pyrrolo-tetrahydroisoquinolones and pyrrolo-benzazepinones
  作者：Frank D. King、Abil E. Aliev、Stephen Caddick、Royston C. B. Copley

  DOI：10.1039/b907400g

  日期：——

  N-arylethyl-acylpyrrolidinium ions gave moderate to good yields of pyrrolo-tetrahydroisoquinolones and pyrrolo-benzazepinones respectively. Electron-donating R substituents enhanced the rate of reaction and gave higher yields than electron-withdrawing substituents. Substituents on the methyl or ethyl chain in general enhanced the reaction, unless sterically encumbered. The equivalent acylpiperidinium ions cyclised much

  三氟甲磺酸介导的N-芳基甲基-和N-芳基乙基-酰基吡咯烷鎓离子的环化分别给出了中等至良好的吡咯并四氢异喹啉酮和吡咯并苯并b庚酮的产率。供电子的R取代基比吸电子的取代基提高了反应速率并提供了更高的产率。除非空间上阻碍，否则甲基或乙基链上的取代基通常会增强反应。等效的酰基哌啶鎓离子环化的速度慢得多，产率也低。
• Triflic Anhydride Promoted Decarboxylative Functionalization of α-Amino Acids
  作者：Mingyue Yuan、Mingliang Lou、Gen Li、Xiangbing Qi

  DOI：10.1021/acs.orglett.4c02589

  日期：2024.9.6

  The decarboxylation of naturally abundant amino acids, followed by subsequent inter- or intramolecular reaction cascades, enables the rapid synthesis of a variety of diverse and high-value amine derivatives. Previous methods have relied heavily on transition metals, involved tedious procedures, or required harsh conditions. Herein, we present a novel reaction cascade for the decarboxylation and nucleophilic

  天然丰富的氨基酸脱羧，随后进行分子间或分子内级联反应，能够快速合成各种不同的高价值胺衍生物。以前的方法严重依赖过渡金属，涉及繁琐的程序或需要恶劣的条件。在此，我们提出了一种用于 α-氨基酸脱羧和亲核功能化的新型反应级联。该方法具有不含过渡金属、操作方便、环境友好、条件温和的特点。
• Efficient Syntheses of Crispine A and Harmicine by Rh-Catalyzed Cyclohydrocarbonylation
  作者：Wen-Hua Chiou、Gau-Hong Lin、Che-Cheng Hsu、Stephen J. Chaterpaul、Iwao Ojima

  DOI：10.1021/ol900702t

  日期：2009.6.18

  The first examples of Rh-catalyzed cyclohydrocarbonylation-bicyclization of N-allylic amides of arylacetic acids are reported. This novel carbonylative bicyclization process was successfully applied to the rapid syntheses of crispine A and its analogues (tricyclic indolizidine alkaloids) as well as harmicine (tetracyclic beta-carboline alkaloid).
• A facile three-step synthesis of (±)-crispine A via an acyliminium ion cyclisation
  作者：Frank D. King

  DOI：10.1016/j.tet.2006.12.041

  日期：2007.2

  A high yielding cyclisation of the readily available N-(4,4-diethoxybutyl)-2-(3,4-dimethoxyphenyl)acetamide to 8,9-bis(methyloxy)-2,3,6, 10b-tetrahydropyrrolo[2, I-a]isoquinolin-5(1H)-one is described. The latter can be reduced with either AlH3 or BH3 to (+/-)-crispine A in an overall yield of 55%. (c) 2006 Elsevier Ltd. All fights reserved.