1-(甲氧基甲基)-5-硝基吲哚 | 120627-42-1

• 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
• 中文名称: 1-(甲氧基甲基)-5-硝基吲哚
• 英文名称: 1-(methoxymethyl)-5-nitro-1H-indole
• 英文别名: 1-methoxymethyl-5-nitro-1H-indole；1-methoxymethyl-5-nitroindole；1H-Indole, 1-(methoxymethyl)-5-nitro-；1-(methoxymethyl)-5-nitroindole
• CAS: 120627-42-1
• 化学式: C₁₀H₁₀N₂O₃
• 分子量: 206.201
• InChiKey: DUOIRVICHHHEHV-UHFFFAOYSA-N

物化性质

• 熔点：
  80-84 °C
• 沸点：
  357.2±22.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  60
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(甲氧基甲基)-5-硝基吲哚 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 1-methoxymethyl-5-amino-1H-indole
  参考文献：
  名称：

  3-Substituted 7-Phenyl-Pyrroloquinolinones Show Potent Cytotoxic Activity in Human Cancer Cell Lines

  摘要：

  A novel series of 3-alkyl-substituted 7-phenyl-3H-pyrrolo[3,2-jlquinolin-9-ones (7-PPyQs) was synthesized with the aim to optimize the cytotoxic activity of recently identified PPyQs, promising inhibitors of tubulin polymerization. All compounds inhibited the growth of 11 human tumor cell lines at submicromolar concentrations as well as two human resistant cancer sublines, A549-T12 and A549-T24. FACS analysis indicated that all compounds caused significant arrest of the A549 cell cycle in G(2)/M phase at 0.1 and 1 mu M and a good correlation between the cytotoxicity IC50 and their ability to block the cell cycle was observed.

  DOI：

  10.1021/jm070534b
• 作为产物：
  描述：

  5-硝基吲哚 、 氯甲基甲基醚 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以94%的产率得到1-(甲氧基甲基)-5-硝基吲哚
  参考文献：
  名称：

  氮杂和吲哚/吡咯核的氧化 C-H/C-H 偶联：钯催化和合成 Eudistomin U

  摘要：

  我们开发了钯催化的吲哚或吡咯与吖嗪 N-氧化物的 C-H/C-H 偶联反应。反应选择性地在吲哚/吡咯的 C3 位和 C2 位进行...

  DOI：

  10.1246/cl.2011.555

文献信息

• Regioselective Oxidative Arylation of Indoles Bearing <i>N-</i>Alkyl Protecting Groups: Dual C−H Functionalization via a Concerted Metalation−Deprotonation Mechanism
  作者：Shathaverdhan Potavathri、Kyle C. Pereira、Serge I. Gorelsky、Andrew Pike、Alexis P. LeBris、Brenton DeBoef

  DOI：10.1021/ja107159b

  日期：2010.10.20

  The most direct method for synthesizing 2-arylindoles is oxidative coupling of an arene with an indole. We have shown that both the activity and regioselectivity of this cross-coupling reaction are correlated with the acidity of the medium. This insight has been applied to predict the best conditions for the oxidative cross-coupling of N-alkylindoles, an important class of substrates that has heretofore

  合成 2-芳基吲哚最直接的方法是芳烃与吲哚的氧化偶联。我们已经表明，这种交叉偶联反应的活性和区域选择性都与培养基的酸度有关。这一见解已被应用于预测 N-烷基吲哚氧化交叉偶联的最佳条件，这是一类重要的底物，迄今为止与氧化交叉偶联所需的苛刻条件不相容。实验和计算数据都表明，无论芳烃上的取代如何，吲哚和简单芳烃的 CH 钯化机制最好描述为协同金属化 - 去质子化。
• Catalytic enantioselective C–H functionalization of indoles with α-diazopropionates using chiral dirhodium(II) carboxylates: asymmetric synthesis of the (+)-α-methyl-3-indolylacetic acid fragment of acremoauxin A
  作者：Takayuki Goto、Yoshihiro Natori、Koji Takeda、Hisanori Nambu、Shunichi Hashimoto

  DOI：10.1016/j.tetasy.2011.05.011

  日期：2011.4

  first catalytic asymmetric synthesis of the (+)-α-methyl-3-indolylacetic acid fragment of acremoauxin A, a potent plant-growth inhibitor. Furthermore, the Fujioka protocol using a combination of TMSOTf and 2,2′-bipyridyl was shown to be superior for the removal of the N-MOM group.

  N-甲氧基甲基（MOM）保护的2,3-未取代的吲哚与α-重氮丙酸酯的对映选择性C–H功能化是通过四[二] [ N-邻苯二甲酰基-（S）-三乙基丙氨酸]铑（Rh 2）催化实现的。（（S）-PTTEA）4，以高收率提供对映体选择性高达86％ee的α-甲基-3-吲哚基乙酸酯。该协议的有效性通过强力植物生长素Acremoauxin A的（+）-α-甲基-3-吲哚基乳酸片段的首次催化不对称合成得到证明。此外，结合使用TMSOTf和2,2'-联吡啶的Fujioka协议被证明对于去除N更为有效。-妈妈组。
• Vicarious Nucleophilic Substitution of Hydrogen in 5- and 6-Nitroindole Derivatives
  作者：Krzysztof Wojciechowski、Mieczysław Makosza

  DOI：10.1055/s-1989-34082

  日期：——
• WOJCIECHOWSKI, KRZYSZTOF;MAKOSZA, MIECZYSLAW, SYNTHESIS,(1989) N, C. 106-109
  作者：WOJCIECHOWSKI, KRZYSZTOF、MAKOSZA, MIECZYSLAW

  DOI：——

  日期：——
• 3-Substituted 7-Phenyl-Pyrroloquinolinones Show Potent Cytotoxic Activity in Human Cancer Cell Lines
  作者：Venusia Gasparotto、Ignazio Castagliuolo、Maria Grazia Ferlin

  DOI：10.1021/jm070534b

  日期：2007.11.1

  A novel series of 3-alkyl-substituted 7-phenyl-3H-pyrrolo[3,2-jlquinolin-9-ones (7-PPyQs) was synthesized with the aim to optimize the cytotoxic activity of recently identified PPyQs, promising inhibitors of tubulin polymerization. All compounds inhibited the growth of 11 human tumor cell lines at submicromolar concentrations as well as two human resistant cancer sublines, A549-T12 and A549-T24. FACS analysis indicated that all compounds caused significant arrest of the A549 cell cycle in G(2)/M phase at 0.1 and 1 mu M and a good correlation between the cytotoxicity IC50 and their ability to block the cell cycle was observed.