(6-甲氧基-1H-吲哚-2-基)甲醇 | 30464-85-8

• 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: (6-甲氧基-1H-吲哚-2-基)甲醇
• 英文名称: (6-methoxy-1H-indol-2-yl)methanol
• CAS: 30464-85-8
• 化学式: C₁₀H₁₁NO₂
• mdl: MFCD11040679
• 分子量: 177.203
• InChiKey: DOFZEVWRABHSQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6-甲氧基-1H-吲哚-2-基)甲醇 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 ammonium acetate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.5h， 生成 2-(6-methoxy-1H-indol-2-yl)ethanamine
  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：

  6-甲氧基-1H-吲哚-2-羧酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (6-甲氧基-1H-吲哚-2-基)甲醇
  参考文献：
  名称：

  利血平生物碱的扭矩选择性 6π 电环化方法

  摘要：

  高度扭矩选择性的热三烯6π电环化控制利血平型生物碱的十二氢吲哚并[2,3- a ]苯并[ g ]喹嗪骨架的C3和C18立构中心之间的相对立体化学。采用串联交叉偶联/电环化方案使我们能够形成必要的三烯并确保其随后的环化。一种新型低温二溴乙烯酮缩醛克莱森重排建立了钯催化交叉偶联反应所需的环外二烯基溴化物前体。

  DOI：

  10.1021/ol302265z

文献信息

• Carbene‐Catalyzed Enantioselective Aromatic N‐Nucleophilic Addition of Heteroarenes to Ketones
  作者：Yonggui Liu、Guoyong Luo、Xing Yang、Shichun Jiang、Wei Xue、Yonggui Robin Chi、Zhichao Jin

  DOI：10.1002/anie.201912160

  日期：2020.1.2

  and optical purities. Our reaction involves the formation of an unprecedented aza-fulvene-type acylazolium intermediate. A broad range of N-heteroaromatic aldehydes and electron-deficient ketone substrates works effectively in this transformation. Several of the chiral N,O-acetal products afforded through this protocol exhibit excellent antibacterial activities against Ralstonia solanacearum (Rs) and

  杂芳基醛的芳族氮原子被卡宾催化剂活化以与酮亲电子试剂反应。以良好至优异的产率和光学纯度提供多功能的环状N，O-乙缩醛产物。我们的反应涉及空前的氮杂富烯型酰基唑鎓中间体的形成。各种各样的N-杂芳族醛和缺电子的酮底物可以有效地实现这种转化。通过该协议提供的几种手性N，O-乙缩醛产品表现出优异的抗青枯菌（Rsstonia solanacearum）的抗菌活性，在开发用于植物保护的新型农业化学品中具有重要的价值。
• 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。
• Gold(I)-Catalyzed Synthesis of Tetrahydrocarbazoles<i>via</i>Cascade [3,3]-Propargylic Rearrangement/[4+2] Cycloaddition of Vinylindoles and Propargylic Esters
  作者：Valentina Pirovano、Elisa Arpini、Monica Dell'Acqua、Rubén Vicente、Giorgio Abbiati、Elisabetta Rossi

  DOI：10.1002/adsc.201500913

  日期：2016.2.4

  A gold(I)‐catalyzed cascade [3,3]‐propargylic rearrangement and [4+2] cycloaddition reaction of 2‐vinylindoles with propargylic esters is reported. The reaction leads to the synthesis of highly substituted tetrahydrocarbazole derivatives in high yields and diasteroselectivities. Furthermore, a preliminary screening for an asymmetric version of this reaction is described.

  报道了2-乙烯基吲哚与炔丙基酯的金（I）催化级联[3,3]-炔丙基重排和[4 + 2]环加成反应。该反应导致以高产率和非对映选择性合成高度取代的四氢咔唑衍生物。此外，描述了对该反应的不对称形式的初步筛选。
• A Torquoselective 6π Electrocyclization Approach to Reserpine Alkaloids
  作者：Gregg A. Barcan、Ashay Patel、K. N. Houk、Ohyun Kwon

  DOI：10.1021/ol302265z

  日期：2012.11.2

  A highly torquoselective thermal triene 6π electrocyclization controls the relative stereochemistry between the C3 and C18 stereocenters of the dodecahydroindolo[2,3-a]benzo[g]quinolizine skeleton of reserpine-type alkaloids. Employing a tandem cross-coupling/electrocyclization protocol allowed us to form the requisite triene and ensure its subsequent cyclization. A novel low-temperature dibromoketene

  高度扭矩选择性的热三烯6π电环化控制利血平型生物碱的十二氢吲哚并[2,3- a ]苯并[ g ]喹嗪骨架的C3和C18立构中心之间的相对立体化学。采用串联交叉偶联/电环化方案使我们能够形成必要的三烯并确保其随后的环化。一种新型低温二溴乙烯酮缩醛克莱森重排建立了钯催化交叉偶联反应所需的环外二烯基溴化物前体。