1-甲基-6-苯基甲氧基吲哚 | 61675-16-9

• 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-甲基-6-苯基甲氧基吲哚
• 英文名称: 6-(benzyloxy)-1-methyl-1H-indole
• 英文别名: 1-methyl-6-phenylmethoxyindole
• CAS: 61675-16-9
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: AEFUSISIFJGCHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-甲基-6-苯基甲氧基吲哚 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 生成 ethyl 2-(6-(benzyloxy)-1-methyl-1H-indol-3-yl)-2-oxoacetate
  参考文献：
  名称：

  Structure-Based Design Leads to the Identification of Lithium Mimetics That Block Mania-like Effects in Rodents. Possible New GSK-3β Therapies for Bipolar Disorders

  摘要：

  More than two million American adults, or approximately one percent of the population 18 years or older, suffer from bipolar disorder. Current treatments include the so-called "mood stabilizers," lithium and valproic acid. Both are relatively dated drugs that are only partially effective and produce various undesirable side effects including weight gain. Based upon continued efforts to understand the molecular target for lithium, it now appears that specific inhibitors of the enzyme glycogen synthase kinase-3 beta (GSK-3 beta) may mimic the therapeutic action of mood stabilizers and might therefore allow for the design of improved drugs for treating patients with bipolar disorder as well as certain neurodegenerative disorders. Furthermore, the pro-apoptotic properties of the GSK-3 enzyme suggest the possible use of such inhibitors as neuroprotective agents. In fact, neuroprotection may contribute to the treatment of mood disorders. The present chemistry, modeling, and biology efforts have identified 3-benzofuranyl-4-indolylmaleimides as potent and relatively selective GSK-3 beta inhibitors. The best ligand in this series (having a K-i value of 4.6 nM against GSK-3 beta) was studied in a novel mouse model of mania that has recently been validated with several clinically effective mood stabilizers. This study presents the first demonstration of the efficacy of a GSK-3 beta inhibitor in this mouse model of mania. Selective brain penetrable GSK-3 ligands like those described herein become valuable research tools in better defining the role of this multifaceted kinase in both physiological and pathophysiological events.

  DOI：

  10.1021/ja068969w
• 作为产物：
  描述：

  6-苄氧基吲哚 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以98 %的产率得到1-甲基-6-苯基甲氧基吲哚
  参考文献：
  名称：

  涉及 HCFO-1233zd 的钯催化吲哚/吡咯羰基化反应 (E)

  摘要：

  介绍了一种Pd(0)催化羰基化合成三氟甲基化3-吲哚酮的新方法。在没有添加剂的情况下，1-氯-3,3,3-三氟丙基（一种廉价且环保的三氟甲基合成嵌段）与吲哚和一氧化碳反应生成三氟甲基吲哚酮，具有良好的产率、区域选择性和化学选择性；此外，该产品对炔烃、醛和酯等碱性官能团表现出很强的耐受性。

  DOI：

  10.1002/chem.202304056

文献信息

• NEW AMINOTHIAZOLES AS FBPASE INHIBITORS FOR DIABETES
  申请人：Hebeisen Paul

  公开号：US20090143448A1

  公开（公告）日：2009-06-04

  Compounds of formula (I) as well as pharmaceutically acceptable salts and esters thereof, wherein R 1 to R 3 have the significance given in claim 1 and which can be used in the form of pharmaceutical compositions.

  式(I)的化合物以及其药用可接受的盐和酯，其中R1至R3具有权利要求1中给定的含义，并可用于制成药物组合物。
• Indolyne Experimental and Computational Studies: Synthetic Applications and Origins of Selectivities of Nucleophilic Additions
  作者：G-Yoon J. Im、Sarah M. Bronner、Adam E. Goetz、Robert S. Paton、Paul H.-Y. Cheong、K. N. Houk、Neil K. Garg

  DOI：10.1021/ja1086485

  日期：2010.12.22

  conditions, trapped by a variety of nucleophilic reagents, and used to access a number of novel substituted indoles. Nucleophilic addition reactions to indolynes proceed with varying degrees of regioselectivity; distortion energies control regioselectivity and provide a simple model to predict the regioselectivity in the nucleophilic additions to indolynes and other unsymmetrical arynes. This model

  4,5-、5,6- 和 6,7-吲哚炔前体的有效合成从商业上可获得的羟基吲哚衍生物开始已有报道。合成路线是通用的，并允许获得在吡咯环上保持未取代的吲哚炔前体。Indolynes 可以在温和的氟化物介导的条件下生成，被各种亲核试剂捕获，并用于获取许多新型取代的吲哚。吲哚的亲核加成反应具有不同程度的区域选择性；畸变能控制区域选择性，并提供一个简单的模型来预测吲哚和其他不对称芳烃的亲核加成中的区域选择性。该模型导致设计出具有增强的亲核区域选择性的取代 4,5-吲哚炔。
• Access to Air-Stable 1,3-Diphosphacyclobutane-2,4-diyls by an Arylation Reaction with Arynes
  作者：Yasuhiro Ueta、Koichi Mikami、Shigekazu Ito

  DOI：10.1002/anie.201601907

  日期：2016.6.20

  appropriate conditions afforded the corresponding 1‐aryl 1,3‐diphosphacyclobutane‐2,4‐diyls. The air‐stable open‐shell singlet P‐heterocycles exhibit considerable electron‐donating character, and the aromatic substituent influences the open‐shell character, which is thought to be related to the property of p‐type semiconductivity. The P‐arylated 1,3‐diphosphacyclobutane‐2,4‐diyl systems can be further

  鉴于材料的应用，调节1,3-二磷环丁烷-2-4,2-二基单元的理化性质是有吸引力的。事实证明，使用芳烃对于将相对富电子的芳基取代基安装到开壳单重态P杂环体系中是有效的。用邻位离子处理位阻于1,3-二磷酸环丁烯-4-酯的阴离子在适当的条件下，在氟化物的存在下，使甲硅烷基化的芳基三氟甲磺酸酯产生相应的1-芳基1,3-3-二磷环丁烷-2,4-二基。空气稳定的开壳单线态P杂环具有显着的给电子性，芳香取代基会影响开壳性，这被认为与p型半导电性有关。P芳基化的1,3-二磷酸环丁烷-2,4-二基系统可进一步用作氟化氢（HF）的检测器，这会导致其光吸收特性发生显着变化。
• Visible Light Photocatalytic Aerobic Oxygenation of Indoles and pH as a Chemoselective Switch
  作者：Chenhao Zhang、Sanliang Li、Filip Bureš、Richmond Lee、Xinyi Ye、Zhiyong Jiang

  DOI：10.1021/acscatal.6b01969

  日期：2016.10.7

  d chromophore (DPZ) photocatalyst, aerobic photooxygenation of indoles could produce either isatins or formylformanilides in satisfactory yields by judiciously selecting inorganic salts or modulating the reaction pH. The current chemodivergent method is also effective with 2-substituted indoles, opening straightforward synthetic routes to valuable 2,2-disubstituted 3-oxindoles, formylformanilide derivatives

  开发了一种有效的化学发散策略，用于可见光光催化。在二氰基吡嗪衍生的生色团（DPZ）光催化剂的存在下，通过明智地选择无机盐或调节反应pH，吲哚的需氧光氧化可产生令人满意的产率的靛红或甲酰甲酰苯胺。当前的化学发散方法对于2-取代的吲哚也是有效的，为有价值的2，2-二取代的3-氧吲哚，甲酰基甲酰苯胺衍生物和苯并恶嗪酮开辟了直接的合成路线。涉及循环伏安法研究的机理研究进一步证实，反应pH值会影响DPZ的电化学性能，从而影响吲哚被转化的氧化途径。
• Rhodium(III)‐Catalyzed Regioselective C−H Allylation and Prenylation of Indoles at C4‐Position
  作者：Shang‐Shi Zhang、Yan‐Zhi Liu、Yi‐Chuan Zheng、Hui Xie、Shao‐Yong Chen、Jia‐Lin Song、Bing Shu

  DOI：10.1002/adsc.202100882

  日期：2022.1.4

  Herein, Rh(III)-catalyzed C4-selective C−H allylation and prenylation of indoles by using a weak carbonyl coordination directing group have been reported. By employing 5-methylene-1,3-dioxan-2-ones, 4-vinyl-1,3-dioxolan-2-ones and 2-methyl-2,3-butadiene as scalable cross-coupling partners, these divergent synthesis protocols proceed smoothly under redox-neutral reaction conditions, delivering various

  在本文中，已经报道了通过使用弱羰基配位导向基团，Rh(III) 催化的 C4 选择性 C-H 烯丙基化和吲哚异戊二烯化。通过采用 5-methylene-1,3-dioxan-2-ones、4-vinyl-1,3-dioxolan-2-ones 和 2-methyl-2,3-butadiene 作为可扩展的交叉偶联伙伴，这些不同的合成方案在氧化还原中性反应条件下顺利进行，以中等至满意的产率提供各种烯丙基化和异戊二烯化吲哚。这种转变表现出高官能团兼容性和广泛的底物范围。还完成了放大实验和机理研究。