5,7-dimethoxy-2,3,4,9-tetrahydro-1H-carbazole | 68395-32-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5,7-dimethoxy-2,3,4,9-tetrahydro-1H-carbazole
• 英文别名: 5,7-dimethoxy-1,2,3,4-tetrahydrocarbazole；5,7-dimethoxy-1,2,3,4-tetrahydro-carbazole；5,7-Dimethoxy-1,2,3,4-tetrahydrocarbazol；1H-Carbazole, 2,3,4,9-tetrahydro-5,7-dimethoxy-
• CAS: 68395-32-4
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: DSYDCJSZBORUGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,7-dimethoxy-2,3,4,9-tetrahydro-1H-carbazole 以82%的产率得到
  参考文献：
  名称：

  Black David St. C., Keller Paul A., Kumar Naresh, Austral. J. Chem., 46 (1993) N 6, S 843-862

  摘要：

  DOI：
• 作为产物：
  描述：

  环己酮 、 3,5-二甲氧基苯肼 在 溶剂黄146 作用下， 反应 1.0h， 以31.4%的产率得到5,7-dimethoxy-2,3,4,9-tetrahydro-1H-carbazole
  参考文献：
  名称：

  Hall, Robin J.; Shannon, Patrick V. R.; Oliveira-Campos, Ana M.-F., Journal of Chemical Research, Miniprint, 1992, # 1, p. 114 - 156

  摘要：

  DOI：

文献信息

• Mild and Rapid Pd-Catalyzed Cross-Coupling with Hydrazine in Continuous Flow: Application to the Synthesis of Functionalized Heterocycles
  作者：Andrew DeAngelis、Dong-Hui Wang、Stephen L. Buchwald

  DOI：10.1002/anie.201208544

  日期：2013.3.18

  CN cross‐coupling of aryl chlorides with hydrazine is described. Through the use of continuous flow, the hazards associated with the use of hydrazine in the presence of transition metals are decreased. In addition, multistep flow sequences have also been developed for the generation of functionalized heterocycles utilizing the arylhydrazine intermediates.

  最小化风险：描述了通过芳基氯与肼的CN交叉偶联合成芳基肼的方法。通过使用连续流动，减少了在过渡金属存在下使用肼的危害。另外，还开发了多步流动顺序以利用芳基肼中间体产生官能化的杂环。
• Hexafluoroisopropanol-Mediated Intramolecular Ring-Opening Cyclization of Indolyl-<i>N</i>-Tethered Epoxides: Tether-Length-Controlled Synthesis of 1,7- and 1,2-Fused Indoles
  作者：Arup Jyoti Das、Raju Chouhan、Sajal Kumar Das

  DOI：10.1021/acs.joc.1c00721

  日期：2021.6.18

  position of the indole and epoxide substituents and the tether length separating these two reacting moieties have strong effects on the cyclization. This mild and transition-metal-free protocol delivered pyrrolo[3,2,1-ij]quinolin-5-ols in moderate to good yields from substrates bearing both a methylene linker that connects the indole and epoxide moieties and an electron-rich indole carbocyclic ring. Notably

  尽管能够以完全原子经济性和高化学选择性、区域选择性、对映选择性和非对映选择性构建苯并稠合杂环，但分子内弗里德尔-克拉夫茨环氧化物芳烃环化（IFCEAC）在有机合成中仍未得到充分利用。因此，这种强大的 Csp 2 -Csp 3键形成反应的广泛适应性需要对底物范围有广泛的了解，以更好地影响杂环合成。沿着这条路线，我们研究了 IFCEAC 在合成 1,7- 和 1,2-稠合吲哚中的适用性。在本文中，我们报告了我们对六氟-2-丙醇 (HFIP) 介导的易于获得的吲哚基-N 的IFCEAC 的第一个例子的范围和局限性的系统调查结果- 束缚环氧化物。我们观察到吲哚和环氧化物取代基的性质和位置以及分隔这两个反应部分的系链长度对环化有很强的影响。这种温和且不含过渡金属的方案从带有连接吲哚和环氧化物部分的亚甲基接头和富电子吲哚的底物中以中等至良好的产率提供吡咯并[3,2,1- ij ]喹啉-5-醇碳环。值得
• Black, David St. C.; Keller, Paul A.; Kumar, Naresh, Australian Journal of Chemistry, 1993, vol. 46, # 6, p. 843 - 862
  作者：Black, David St. C.、Keller, Paul A.、Kumar, Naresh

  DOI：——

  日期：——
• Binding of methoxy-substituted N1-benzenesulfonylindole analogs at human 5-HT6 serotonin receptors
  作者：Uma Siripurapu、Renata Kolanos、Małgorzata Dukat、Bryan L. Roth、Richard A. Glennon

  DOI：10.1016/j.bmcl.2006.04.094

  日期：2006.7

  Comparison of several amine-substituted and methoxy-substituted analogs of N-1-(4-aminobenzene)sulfonylindole suggests that these substituents might contribute to the 5-HT6 serotonin receptor affinity of these agents via their electronic effect on the indolic nucleus. Their 1,2,3,4-tetrahydrocarbazole counterparts behave differently. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and pharmacology of a hybrid cannabinoid
  作者：John W. Huffman、Jianzhong Lu、Dong Dai、Aleksandr Kitaygorodskiy、Jenny L. Wiley、Billy R. Martin

  DOI：10.1016/s0968-0896(99)00305-3

  日期：2000.2

  A pentacyclic hybrid cannabinoid (4) has been synthesized, which combines structural elements of traditional cannabinoids and cannabmimetic indoles. Cannabinoid 4 contains a 1-pentylindole structure fused to the 2,3-positions of the partially reduced hydroxydibenzopyran system of THC. The successful approach to 4 employed 9-benzoyl-5,7-dimethoxy-1,2,3,4-tetrahydrocarbazole (17) as the starting material. Dehydrogenation to carbazole 18, followed by demethylation and condensation with trans-p-menthadienol gave N-benzoyl hybrid cannabinoid 22, N-alkylation of which afforded target cannabinoid 4. The hybrid cannabinoid had affinity for the CB1 receptor approximately equal to that of Delta(8)-THC (K-i=19.3+/-3 nM), and shows comparable potency in vivo. (C) 2000 Elsevier Science Ltd. All rights reserved.