4-甲氧基-1H-吲哚-2-甲醛 | 213682-04-3

• 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: 4-甲氧基-1H-吲哚-2-甲醛
• 英文名称: 4-methoxy-1H-indole-2-carbaldehyde
• 英文别名: 4-methoxyindole-2-carboxaldehyde
• CAS: 213682-04-3
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: BMUMJEKBMVREKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-甲氧基-1H-吲哚-2-甲醛 在 lithium aluminium tetrahydride 、 ammonium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 生成 2-(4-甲氧基-1H-吲哚-2-基)-乙胺
  参考文献：
  名称：

  2-[N-Acylamino(C₁−C₃)alkyl]indoles as MT₁ Melatonin Receptor Partial Agonists, Antagonists, and Putative Inverse Agonists

  摘要：

  The synthesis of several novel indole melatonin analogues substituted at the 2-position with acylaminomethyl (8-11), acylaminoethyl (5a-k), or acylaminopropyl (13) side chains is reported. On the basis of a novel in vitro functional assay (specific binding of [S-35]GTP gamma S), which can discriminate agonist from partial agonist, antagonist, and inverse agonist ligands, Ba,g,h,j and 13 were shown to be partial agonists, 5d,e and 8-11 competitive antagonists, and 5b,c,k putative inverse agonists. Binding and functional assays were performed on cloned human MT1 receptor. Structure-activity relationship considerations indicate that N-[1-aryl-2-(4-methoxy-1H-indol-2-yl)(C-1-C-2)alkyl]alkanamides represent a lead structure for this type of ligands.

  DOI：

  10.1021/jm970721h
• 作为产物：
  描述：

  4-甲氧基-1氢-吲哚-2-甲酸乙酯 在 lithium aluminium tetrahydride 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 5.0h， 生成 4-甲氧基-1H-吲哚-2-甲醛
  参考文献：
  名称：

  Rh 催化烯烃氢酰化对映选择性合成多环氮杂环：在没有螯合辅助的情况下构建六元环

  摘要：

  报道了N-烯丙基吲哚-2-甲醛和N-烯丙基吡咯-2-甲醛的催化对映选择性加氢酰化。与形成六元环的许多烯烃加氢酰化相反，这些环化过程是在不存在稳定酰基铑(III)氢化物中间体的辅助官能团的情况下发生的。分子内加氢酰化反应以中等至高产率生成具有优异对映选择性的7,8-二氢吡啶并[1,2- a ]吲哚-9(6 H )-酮和 6,7-二氢吲哚嗪-8(5 H )-酮。

  DOI：

  10.1021/ol501869s

文献信息

• Indolinone derivatives as protein kinase/phosphatase inhibitors
  申请人：——

  公开号：US20020052369A1

  公开（公告）日：2002-05-02

  The present invention relates to certain 2-indolinone compounds which modulate the activity of protein kinases (“PKs”) and phosphatases. The compounds of this invention are therefore useful in treating disorders related to abnormal PK activity. Pharmaceutical compositions comprising these compounds, methods of treating diseases utilizing pharmaceutical compositions comprising these compounds and methods of preparing them are also disclosed.

  本发明涉及调节蛋白激酶（“PKs”）和磷酸酶活性的某些2-吲哚酮化合物。因此，本发明的化合物在治疗与异常PK活性相关的疾病方面是有用的。还公开了包含这些化合物的药物组合物、利用包含这些化合物的药物组合物治疗疾病的方法以及制备它们的方法。
• Addition of a Carbene Catalyst to Indole Aryl Aldehyde Activates a Remote δ-sp² Carbon for Protonation and Formal [4+2] Reaction
  作者：Pengcheng Zheng、Shuquan Wu、Chengli Mou、Wei Xue、Zhichao Jin、Yonggui Robin Chi

  DOI：10.1021/acs.orglett.9b01624

  日期：2019.7.5

  The addition of a carbene catalyst to an indole aryl aldehyde leads to the activation of a remote sp2 carbon that is five atoms away from the catalyst. The unsaturated Breslow intermediate formed between the catalyst and substrate undergoes an internal redox reaction and remote carbon protonation to generate an analogous azolium vinyl enolate intermediate. Subsequent [4+2] reaction with cyclic imine

  将卡宾催化剂添加到吲哚芳基醛中导致远离催化剂五个原子的远程sp 2碳的活化。在催化剂和底物之间形成的不饱和Breslow中间体会经历内部氧化还原反应和远距离的碳质子化反应，从而生成类似的烯醇乙烯基late唑鎓中间体。随后与环亚胺底物的[4 + 2]反应最终得到多环吡啶并吲哚，为几乎单一的非对映异构体，具有出色的对映选择性。
• Enantioselective Synthesis of Polycyclic Nitrogen Heterocycles by Rh-Catalyzed Alkene Hydroacylation: Constructing Six-Membered Rings in the Absence of Chelation Assistance
  作者：Xiang-Wei Du、Avipsa Ghosh、Levi M. Stanley

  DOI：10.1021/ol501869s

  日期：2014.8.1

  Catalytic, enantioselective hydroacylations of N-allylindole-2-carboxaldehydes and N-allylpyrrole-2-carboxaldehydes are reported. In contrast to many alkene hydroacylations that form six-membered rings, these annulative processes occur in the absence of ancillary functionality to stabilize the acylrhodium(III) hydride intermediate. The intramolecular hydroacylation reactions generate 7,8-dihydropyrido[1

  报道了N-烯丙基吲哚-2-甲醛和N-烯丙基吡咯-2-甲醛的催化对映选择性加氢酰化。与形成六元环的许多烯烃加氢酰化相反，这些环化过程是在不存在稳定酰基铑(III)氢化物中间体的辅助官能团的情况下发生的。分子内加氢酰化反应以中等至高产率生成具有优异对映选择性的7,8-二氢吡啶并[1,2- a ]吲哚-9(6 H )-酮和 6,7-二氢吲哚嗪-8(5 H )-酮。
• One-Pot Asymmetric Synthesis of Quaternary Pyrroloindolones through a Multicatalytic N-Allylation/Hydroacylation Sequence
  作者：Hong Lu、Jun-Bing Lin、Jin-Yu Liu、Peng-Fei Xu

  DOI：10.1002/chem.201402947

  日期：2014.9.8

  intramolecular, quaternary carbon center forming hydroacylation of α‐substituted acrylates has been discovered. This interesting transformation can be readily incorporated into a multicatalytic tandem process enabled by a combination of nucleophilic tertiary amine and N‐heterocyclic carbene catalysis. With no additional stoichiometric base required, this transformation affords the quaternary pyrroloindolones

  已经发现了α-取代丙烯酸酯的分子内季碳中心加氢酰化反应。通过亲核叔胺和N-杂环卡宾催化的组合，可以轻松地将此有趣的转化并入多催化串联过程中。无需额外的化学计量基础，该转化即可提供具有高对映选择性的季吡咯并吲哚酮。
• [EN] INHIBITORS OF CHECKPOINT KINASES (WEE1 AND CHK1)<br/>[FR] INHIBITEURS DE CHECKPOINT KINASES (WEE1 ET CHK1)
  申请人：WARNER LAMBERT CO

  公开号：WO2003091255A1

  公开（公告）日：2003-11-06

  This invention relates to pyrrolocarbazole derivatives according formula (I) wherein R1, R2, r7, R8 R9, X and Y are as defined in the specification wherein said derivatives specifically inhibit one or both of the checkpoint kinases Wee1 and Chk1.

  本发明涉及公式（I）中的吡咯并咔唑衍生物，其中R1，R2，r7，R8，R9，X和Y如规范中所定义，其中所述衍生物特异性地抑制检查点激酶Wee1和Chk1中的一个或两个。