6-Nitro-3-methyl-1,2,3,4-tetrahydro-carbazol | 59601-25-1

• 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: 6-Nitro-3-methyl-1,2,3,4-tetrahydro-carbazol
• 英文别名: 3-methyl-6-nitro-2,3,4,9-tetrahydro-1H-carbazole；3-methyl-6-nitro-1,2,3,4-tetrahydro-carbazole；3-Methyl-6-nitro-1,2,3,4-tetrahydro-carbazol
• CAS: 59601-25-1
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: JXVYVRFVPABCLY-UHFFFAOYSA-N

物化性质

• 熔点：
  149-151 °C
• 沸点：
  411.8±40.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Nitro-3-methyl-1,2,3,4-tetrahydro-carbazol 在 钯 氢气 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Isosteric ramatroban analogs: selective and potent CRTH-2 antagonists

  摘要：

  The chemoattractant receptor-homologous molecule expressed on T(H)2 cells (CRTH-2), also found on eosinophils and basophils, is a prostaglandin D-2 receptor involved in the recruitment of these cell types during an inflammatory response. In this report, we describe the synthesis and optimization of a ramatroban isostere that is a selective and potent antagonist of CRTH-2 which may be useful in the treatment of certain diseases. © 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.055
• 作为产物：
  描述：

  4-methyl-cyclohexanone-phenylhydrazone 在 硫酸 、 potassium nitrate 作用下， 生成 6-Nitro-3-methyl-1,2,3,4-tetrahydro-carbazol
  参考文献：
  名称：

  Plant; Rosser, Journal of the Chemical Society, 1928, p. 2461

  摘要：

  DOI：

文献信息

• Novel SO3H-functionalized ionic liquids catalyzed a simple, green and efficient procedure for Fischer indole synthesis in water under microwave irradiation
  作者：Bai Lin Li、Dan-Qian Xu、Ai Guo Zhong

  DOI：10.1016/j.jfluchem.2012.09.010

  日期：2012.12

  ionic liquids were successfully applied as catalysts for one-pot Fischer indole synthesis under microwave irradiation and in a water medium. Various types of indoles were prepared using single-carbonyl ketones/aldehydes or cyclohexandiones with aryhydrazine hydrochlorides in 86–96% yields in water under microwave irradiation. The indole products could be conveniently separated from the reaction mixture

  新型SO 3 H官能化离子液体已成功地用作微波辐射下和在水介质中一锅费休吲哚合成的催化剂。在微波辐射下，使用单羰基酮/醛或环己二酮与盐酸肼肼制备的各种类型的吲哚，在水中的产率为86-96％。吲哚产物可通过过滤方便地从反应混合物中分离出来，并且[（HSO 3 -p）2 im] [CF 3 SO 3 ] / H 2 O的催化体系可直接重复使用而无需任何处理。整个过程简单，省时且环保。
• Fischer indole synthesis catalyzed by novel SO3H-functionalized ionic liquids in water
  作者：Dan-Qian Xu、Jian Wu、Shu-Ping Luo、Ji-Xu Zhang、Jia-Yi Wu、Xiao-Hua Du、Zhen-Yuan Xu

  DOI：10.1039/b901010f

  日期：——

  the one-pot Fischer indole synthesis in water medium. The sequence of the catalytic activity observed in the transformation was in good agreement with the Brønsted acidity order determined by the Hammett method. Various types of indoles from single-carbonyl ketones/aldehydes and cyclohexandiones were provided in 68–96% yields using the catalytic system of [(HSO3-p)2im][HSO4]/H2O. The indole products could

  新型SO 3 H功能化离子液体 在咪唑鎓中带有两个烷基磺酸基团 阳离子 被设计并成功应用于 催化剂 一锅费歇尔 吲哚 合成中 水中等的。在转化中观察到的催化活性的顺序与通过哈米特方法测定的布朗斯台德酸度顺序非常一致。各种类型吲哚 从单羰 酮类/醛类并使用[（HSO 3 -p）2 im] [HSO 4 ] /催化体系提供了环己二酮，产率为68-96％。高氧2。这吲哚 可以方便地从反应混合物中分离出产物 过滤 和解散 催化剂 可以通过用强酸处理来再生 阳离子 交换树脂，这意味着整个过程都在 水 不使用任何有机物 溶剂。
• Potential Inhibitors of Tyrosine Hydroxylase and Dopamine-β-Hydroxylase
  作者：K.R. Scott、Calvin J. Alt、Murray Kemp、Elise Hayes、Vasant G. Telang

  DOI：10.1002/jps.2600731109

  日期：1984.11

  A series of methyl-substituted 1,2,3,4-tetrahydrocarbazoles was synthesized and screened for in vitro activity against tyrosine hydroxylase and dopamine-β-hydroxylase. The most potent compounds were evaluated for inhibition of norepinephrine biosynthesis in rats. The results indicated no significant decrease in norepinephrine levels at three dosage levels.

  合成了一系列甲基取代的1,2,3,4-四氢咔唑，并筛选了针对酪氨酸羟化酶和多巴胺-β-羟化酶的体外活性。评价了最有效的化合物对大鼠去甲肾上腺素生物合成的抑制作用。结果表明在三种剂量水平下去甲肾上腺素水平没有显着降低。
• TRICYCLIC COMPOUNDS
  申请人：Meiji Seika Kaisha, Ltd.

  公开号：EP1184373A1

  公开（公告）日：2002-03-06

  A compound represented by the formula (I) [A represents a 5- to 7-membered hydrocarbon ring group; L represents -NR3-CO-, -CO-NR3- and the like (R3 represents a hydrogen atom, a lower alkyl group, a lower acyl group and the like); M represents an alkylene linking group (a carbon atom constituting the carbon chain may be replaced with a nitrogen atom, an oxygen atom and the like); X represents -S-, -O-, -NR4-, -NR5-CO- and the like (R4 and R5 represent a hydrogen atom, a lower alkyl group and the like) or a single bond; Y represents an alkyl group, an aryl group, an amino group, an aromatic heterocyclic group and the like; R1 represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a lower acyl group; and R21, R22 and R23 represent a hydrogen atom, a hydroxyl group, a lower alkyl group and the like] or a salt thereof. The compound is useful as an active ingredient of medicaments for diseases in which neuropeptide Y is involved, ingestion control for hyperphagia and the like.

  由式（I）代表的化合物[A 代表 5 至 7 元烃环基；L 代表-NR3-CO-、-CO-NR3-等（R3 代表氢原子、低级烷基、低级酰基等）；M 代表亚烷基连接基团（构成碳链的碳原子可以用氮原子、氧原子等取代）；X 代表-S-、-O-、-NR4-、-NR5-CO-等（R4 和 R5 代表氢原子、低级烷基等）或单键；Y 代表烷基、芳基、氨基、芳香杂环基等；R1代表低级烷基、低级烯基、低级炔基或低级酰基；以及 R21、R22 和 R23 代表氢原子、羟基、低级烷基等]或其盐。该化合物可用作治疗涉及神经肽 Y 的疾病的药物的活性成分、控制食欲亢进的药物等。
• US6713473B1
  申请人：——

  公开号：US6713473B1

  公开（公告）日：2004-03-30