1-methyl-4,6-dimethoxyindole | 134914-43-5

• 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: 1-methyl-4,6-dimethoxyindole
• 英文别名: 4,6-dimethoxy-1-methylindole；4,6-dimethoxyindole；4,6-Dimethoxy-1-methyl-1h-indole
• CAS: 134914-43-5
• 化学式: C₁₁H₁₃NO₂
• mdl: MFCD07364586
• 分子量: 191.23
• InChiKey: ZTBQXHCHQUPVFZ-UHFFFAOYSA-N

物化性质

• 沸点：
  332.0±22.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  23.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-4,6-dimethoxyindole 在 sodium tetrahydroborate 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 3-hydroxymethyl-4,6-dimethoxy-1-methylindole
  参考文献：
  名称：

  Synthesis of indolocyclotriveratrylenes

  摘要：

  Indolocyclotriveratrylenes linked through C2 and C3 can be prepared by acid-catalysed reactions of indole-2- or -3-methanols. The initial example, compound 1 has been confirmed, and an X-ray crystal structure is reported. Seven new examples of indolocyclotriveratrylenes, namely 7, 9, 11, 13,17, 28 and 29 are described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.092
• 作为产物：
  描述：

  4,6-二甲氧基吲哚 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以100%的产率得到1-methyl-4,6-dimethoxyindole
  参考文献：
  名称：

  Elaboration of Simplified Vinca Alkaloids and Phomopsin Hybrids

  摘要：

  Nine simplified vinca alkaloids and phomospin A hybrids, in which vindoline moiety has been replaced by a simpler scaffold, have been elaborated to evaluate their activity on the inhibition of tubulin polymerization. This article deals with the synthesis of various simplified vinca alkaloids, using a stereoselective coupling of catharantine with reactive aromatic compounds and methanol as well as their subsequent condensation with a large peptide chain mimicking those of phomopsin A. Biological evaluation and molecular modeling studies are also reported.

  DOI：

  10.1111/j.1747-0285.2009.00922.x

文献信息

• Mechanism-controlled regioselective synthesis of indolyl benzo[b]carbazoles
  作者：David StC. Black、Donald C. Craig、Mardi Santoso

  DOI：10.1016/s0040-4039(99)01268-x

  日期：1999.9

  Benzo[b]carbazoles can be synthesised readily and in good yields from the combination of 2,3-unsubstituted indoles and o-phthaldialdehyde in the presence of acid catalysts. Use of phosphoryl chloride in chloroform gives rapid reactions and yields 11-(3-indolyl)benzo[b]carbazoles, whereas the use of p-toluenesulfonic acid in methanol gives slow reactions and yields the isomeric 6-(3-indolyl)benzo[b]carbazoles

  在酸催化剂的存在下，由2，3-未取代的吲哚和邻苯二甲醛的组合可以容易地并且以高收率合成苯并[ b ]咔唑。在氯仿中使用磷酰氯可快速反应，生成11-（3-吲哚基）苯并[ b ]咔唑，而在甲醇中使用对甲苯磺酸，则反应缓慢，并生成异构体6-（3-吲哚基）苯并[ b ]咔唑。
• Compound inhibiting dipeptidyl peptidase IV
  申请人：Kakigami Takuji

  公开号：US20060229286A1

  公开（公告）日：2006-10-12

  A dipeptidyl peptidase IV inhibitor which is satisfactory in respect of activity, stability and safety and has an excellent action as a pharmaceutical agent. A compound represented by the following general formula or a pharmaceutically acceptable salt thereof: wherein R 1 and R 2 each represents hydrogen, an optionally substituted C1-6 alkyl group, or —COOR 5 whereupon R 5 represents hydrogen or an optionally substituted C1-6 alkyl group, or R 1 , R 2 , and a carbon atom together represent a 3- to 6-membered cycloalkyl group, R 3 represents hydrogen or an optionally substituted C6-10 aryl group, R 4 represents a hydrogen or a cyano group, D represents —CONR 6 —, —CO— or —NR 6 CO—, R 6 represents hydrogen or an optionally substituted C1-6 alkyl group, E represents —(CH 2 ) m — whereupon m is 1 to 3, —CH 2 OCH 2 —, or —SCH 2 —, n is 0 to 3, and A represents an optionally substituted bicyclic heterocyclic group or bicyclic hydrocarbon group.

  一种二肽基肽酶IV抑制剂，具有活性、稳定性和安全性方面的满意度，并且作为药物剂量具有优异的作用。该化合物由以下通式表示或其药学上可接受的盐：其中R1和R2分别表示氢、可选取代的C1-6烷基或-COOR5，其中R5表示氢或可选取代的C1-6烷基，或者R1、R2和一个碳原子共同表示3-6个成员的环烷基，R3表示氢或可选取代的C6-10芳基，R4表示氢或氰基，D表示-CONR6-、-CO-或-NR6CO-，R6表示氢或可选取代的C1-6烷基，E表示-(CH2)m-，其中m为1至3，-CH2OCH2-或-SCH2-，n为0至3，A表示可选取代的双环杂环基或双环烃基。
• SCHWEINFURTHIN ANALOGUES
  申请人：University of Iowa Research Foundation

  公开号：US20150045404A1

  公开（公告）日：2015-02-12

  The invention provides a compound of formula (I): wherein R 1 -R 5 have any of the values defined in the specification. The compounds are useful for the treatment of cancer and other diseases.

  本发明提供了一个化合物的公式(I)：其中R1-R5具有规范中定义的任何值。这些化合物对于治疗癌症和其他疾病是有用的。
• Acid-catalysed reaction of activated indoles with methyl ketones
  作者：David St.C. Black、Donald C. Craig、Naresh Kumar

  DOI：10.1016/s0040-4039(00)74279-1

  日期：1991.3

  4,6-Dimethoxy-3-methylindole can be converted by treatment with acetone or acetophenones in methanolic hydrochloric acid into ring-fused indoles in good yields.
• US7345180B2
  申请人：——

  公开号：US7345180B2

  公开（公告）日：2008-03-18