1,2-Dimethoxycarbonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole | 79465-82-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2-Dimethoxycarbonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole
• 英文别名: L-(2β,3aα,8aα)-1,2,3,3a,8,8a-hexahydro-1,2-dimethoxycarbonylpyrrolo<2,3-b>indole；hexahydropyrrolo<2,3-b>indole；dimethyl (2S,3aR,8aS)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate；dimethyl (2S,3aR,8bR)-2,3a,4,8b-tetrahydro-1H-pyrrolo[2,3-b]indole-2,3-dicarboxylate
• CAS: 79465-82-0
• 化学式: C₁₄H₁₆N₂O₄
• 分子量: 276.292
• InChiKey: UNJSYLFJPUKBGL-ADEWGFFLSA-N

物化性质

• 沸点：
  398.4±42.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-Dimethoxycarbonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 溶剂黄146 为溶剂， 生成 5-Cyano-N_b-methoxycarbonyl-N_a-acetyl-L-tryptophan methyl esterolo<2,3-b>indole
  参考文献：
  名称：

  Synthesis of 5-cyano-l-tryptophan

  摘要：

  The 5-bromo derivative 2 of the cyclic tautomer of N(b)-methoxycarbonyl-L-tryptophan methyl ester 1 undergoes reaction with CuCN in refluxing N-methylpyrrolidone (NMP) to give 5-cyano derivative 3a with some ring opened 5-cyano product 3b. Both 3a and 3b can be converted, in high yield, into free 5-cyano-L-tryptophan 4 with BBr3 under mild conditions.

  DOI：

  10.1016/s0040-4039(00)77665-9
• 作为产物：
  描述：

  N-(methoxycarbonyl)-L-tryptophan methyl ester 在 磷酸 作用下， 反应 3.0h， 以100%的产率得到1,2-Dimethoxycarbonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole
  参考文献：
  名称：

  色氨酸-六氢吡咯并吲哚合成中的正交保护基团

  摘要：

  此处描述了在六氢吡咯并 [2,3-b] 吲哚和吲哚色氨酸之间包含 aC3a-Ni 键的各种多环系统的合成。进行了一系列实验以确定五个正交保护基团的最佳组合和形成所述键的最佳反应条件，这是许多最近发现的海洋天然产物的共同特征。

  DOI：

  10.1002/ejoc.201101057

文献信息

• Orthogonal Protecting Groups in the Synthesis of Tryptophanyl-Hexahydropyrroloindoles
  作者：Pau Ruiz-Sanchis、Svetlana A. Savina、Gerardo A. Acosta、Fernando Albericio、Mercedes Álvarez

  DOI：10.1002/ejoc.201101057

  日期：2012.1

  The synthesis of various polycyclic systems containing aC3a–Ni bond between a hexahydropyrrolo[2,3-b]indole and an indole tryptophan is described here. A series of experiments were performed to determine the best combination of five orthogonal protecting groups and the best reaction conditions for formation of said bond, which is a common feature among many recently discovered marine natural products

  此处描述了在六氢吡咯并 [2,3-b] 吲哚和吲哚色氨酸之间包含 aC3a-Ni 键的各种多环系统的合成。进行了一系列实验以确定五个正交保护基团的最佳组合和形成所述键的最佳反应条件，这是许多最近发现的海洋天然产物的共同特征。
• Synthesis and fungicidal activity of tryptophan analogues – the unexpected calycanthaceous alkaloid derivatives
  作者：Shaojun Zheng、Yongdong Gu、Longbo Li、Rui Zhu、Xingwei Cai、Hongjin Bai、Jiwen Zhang

  DOI：10.1080/14786419.2016.1230117

  日期：2017.5.19

  21 N-protected tryptophan derivatives were synthesised from tryptophan in good yields. Their structures were characterised by IR, 1H NMR, 13C NMR, DEPT (90° and 135°) and MS analysis. The synthesised compounds were evaluated against a wide variety of plant pathogen fungi. Compounds a19 and a21 displayed activity against Fusarium oxysporum (F. oxysporum), and compound a21 showed high activity against F. oxysporum

  从色氨酸以高收率合成了一系列21种N保护的色氨酸衍生物。它们的结构通过IR，1 H NMR，13 C NMR，DEPT（90°和135°）和MS分析来表征。针对多种植物病原体真菌对合成的化合物进行了评估。化合物a19和a21对尖镰刀菌（F. oxysporum）表现出活性，化合物a21对尖孢镰刀菌和茄子黄萎病表现出高活性，EC 50值为58.27和77.39μgmL -1。， 分别。考虑到对标题化合物的生物测定进行了评估，链烷基取代基的作用可能会导致杀真菌效力的显着变化。还讨论了它们的结构-抗真菌活性关系。这些结果将为作为抗菌剂的花椰菜生物碱的进一步设计，结构修饰和开发铺平道路。
• Cyclic tautomers of tryptophans and tryptamines—4
  作者：Mikio Taniguchi、Tohru Hino

  DOI：10.1016/s0040-4020(01)92088-5

  日期：1981.1

  Nb-Methoxycarbonyltryptophan methyl ester (dl- and l-13) was cyclized to the corresponding rans cyclic tautomer (14) in excellent yield in various acids such as 85% phosphoric acid or trifluoroacetic acid. The cis cyclic tautomer (15) was formed as the less stable and kinetically controlled product and converted to the more stable trans isomer (14) under the reaction condition. The trans isomer (14)

  Ñ b -Methoxycarbonyltryptophan甲酯（DL-和1- 13）环化为相应的RANs环状互变异构体（14，在各种酸如85％的磷酸或三氟乙酸优良产率）。的顺式环互变异构体（15）形成为较不稳定的和动力学控制的产品，并转换为更稳定的反式异构体（14反应条件下）。用10％硫酸的甲醇溶液处理，将反式异构体（14）还原为13。其他色氨酸和色胺衍生物（6和19a）在相似的酸性介质中也被环化成相应的环状互变异构体。
• Synthesis and Antibacterial Activity of Calycanthaceous Alkaloid Derivatives
  作者：Shaojun Zheng、Yongdong Gu、Rui Zhu、Longbo Li、Hongjin Bai、Jiwen Zhang

  DOI：10.1007/s10600-018-2274-6

  日期：2018.1

  A series of 45 calycanthaceous alkaloid derivatives with the tetrahydropyrroloindole core structure was synthesized from tryptophan in good yields. The synthesized compounds were evaluated against five strains of bacteria (Bacillus cereus, Bacillus subtilis, Staphylococcus aureus, Escherichia coil, Ralstonia solanacearum, and Pseudomonas aeruginosa). The bioassays indicated that among the synthesized compounds, compounds b3 and b4 exhibited a high degree of activity towards Gram positive B. subtilis. Compounds a14 and a18 displayed a high degree of activity towards R. solanacearum. These results will pave the way for further design, structural modification, and development of calycanthaceous alkaloids as antibacterial agents.

  以色氨酸为原料合成了一系列 45 种具有四氢吡咯吲哚核心结构的钙黄质生物碱衍生物，产量良好。对合成的化合物进行了针对五种菌株（蜡样芽孢杆菌、枯草芽孢杆菌、金黄色葡萄球菌、卷曲杆菌、茄属拉氏菌和铜绿假单胞菌）的评估。生物测定结果表明，在合成的化合物中，化合物 b3 和 b4 对革兰氏阳性枯草杆菌具有很高的活性。化合物 a14 和 a18 对 R. solanacearum 具有很高的活性。这些结果将为进一步设计、结构改造和开发作为抗菌剂的灯盏花生物碱铺平道路。
• Facile nucleophilic substitution at the C3a tertiary carbon of the 3a-bromohexahydropyrrolo[2,3-b]indole scaffold
  作者：Isabel Villanueva-Margalef、David E. Thurston、Giovanna Zinzalla

  DOI：10.1039/c0ob00327a

  日期：——

  The synthesis of 3a-substituted hexahydropyrrolo[2,3-b]indole derivatives via nucleophilic substitution at the C3a position is reported. Nitrogen-, oxygen-, sulfur-, fluoro- and carbon-based nucleophiles have been employed, using both conventional organic solvents and ionic liquids. The C3a-substituted derivatives were obtained in good to excellent yields.

  的合成 3a取代的 六氢吡咯并[2,3- b ]吲哚据报道，在C3a位置上通过亲核取代作用得到的衍生物。氮-，氧-， 硫-，氟-和 碳既使用常规有机溶剂又使用离子液体，已经使用了基于核的亲核试剂。C 3a取代的衍生物以良好至优异的产率获得。