1-(3-methoxybenzyl)-1H-indole | 1225709-69-2

• 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-(3-methoxybenzyl)-1H-indole
• 英文别名: 1-(3-Methoxy-benzyl)-1H-indole；1-[(3-methoxyphenyl)methyl]indole
• CAS: 1225709-69-2
• 化学式: C₁₆H₁₅NO
• mdl: MFCD16319761
• 分子量: 237.301
• InChiKey: HOJYYEVBDCCPFC-UHFFFAOYSA-N

物化性质

• 沸点：
  414.0±28.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.125
• 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-(3-methoxybenzyl)-1H-indole 在 potassium carbonate 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 48.5h， 生成 3-hydroxy-4-(1-(3-methoxybenzyl)-1H-indol-3-yl)butan-2-one
  参考文献：
  名称：

  Synthesis of α-ketols by functionalization of captodative alkenes and divergent preparation of heterocycles and natural products

  摘要：

  Captodative alkene 1-acetylvinyl p-nitrobenzenecarboxylate 1a was evaluated for its reactivity in Lewis acid-catalyzed Michael additions with functionalized benzene rings and heterocycles, leading to diverse conjugated addition adducts. The hydrolysis of the latter resulted in the desired functionalized a-ketols, including natural alkaloid actinopolymorphol B (24a). The alpha-ketol core structure of these compounds was used as the building block for the synthesis of the natural alkaloid tanakine (25) and for the divergent construction of highly substituted heterocycles, such as 4-oxazolin-2-ones and butenolides, and their respective fused polycyclic derivatives. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.07.010
• 作为产物：
  描述：

  吲哚 在 环戊基甲醚 、 palladium diacetate 、 双(三甲基硅烷基)氨基钾 、 caesium carbonate 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 水 为溶剂， 反应 24.0h， 生成 1-(3-methoxybenzyl)-1H-indole
  参考文献：
  名称：

  Suzuki–Miyaura Cross-Coupling of Potassium Trifluoro(N-methylheteroaryl)borates with Aryl and Heteroaryl Halides

  摘要：

  The synthesis of potassium trifluoro(N-methylheteroaryl)borates and their use in cross-coupling reactions with various aryl and heteroaryl halides to construct N-methyl heteroaryl-substituted aromatic and heteroaromatic compounds are reported.

  DOI：

  10.1021/jo4009589

文献信息

• Indole Functionalization via Photoredox Gold Catalysis
  作者：Sherif J. Kaldas、Alexandre Cannillo、Terry McCallum、Louis Barriault

  DOI：10.1021/acs.orglett.5b01260

  日期：2015.6.5

  photoredox catalyst [Au2(dppm)2]Cl2 to initiate free-radical cyclizations onto indoles is reported. Excitation of the dimeric Au(I) photocatalyst for the reduction of unactivated bromoalkanes and bromoarenes is used for the generation of carbon-centered radicals. Previous to this work, reduction processes leading to indole functionalization utilizing photoredox catalysts were limited to activated benzylic

  报道了使用光氧化还原催化剂[Au 2（dppm）2 ] Cl 2来引发在吲哚上的自由基环化。激发二聚体Au（I）光催化剂以还原未活化的溴代烷烃和溴代芳烃用于碳中心自由基的产生。在这项工作之前，利用光氧化还原催化剂导致吲哚官能化的还原过程仅限于活化的苄基或α-羰基定位的溴代烷烃。该方法为有机锡烷和发火引发剂提供了温和且安全的替代方法，可用于获得以前通过催化或化学计量方法无法获得的高能自由基。
• Catalytic Tandem Friedel–Crafts Alkylation/C4–C3 Ring-Contraction Reaction: An Efficient Route for the Synthesis of Indolyl Cyclopropanecarbaldehydes and Ketones
  作者：Francesca Turnu、Alberto Luridiana、Andrea Cocco、Stefania Porcu、Angelo Frongia、Giorgia Sarais、Francesco Secci

  DOI：10.1021/acs.orglett.9b02617

  日期：2019.9.20

  A general strategy for the synthesis of indolyl cyclopropanecarbaldehydes and ketones via a Brønsted acid-catalyzed indole nucleophilic addition/ring-contraction reaction sequence has been exploited. The procedure leads to a wide panel of cyclopropyl carbonyl compounds in generally high yields with a broad substrate scope.

  已经开发了通过布朗斯台德酸催化的吲哚亲核加成/缩环反应序列合成吲哚基环丙烷甲醛和酮的一般策略。该方法导致以宽泛的底物范围通常以高收率获得大量的环丙基羰基化合物。
• A Catalytic One-Pot Synthesis of Indolyl Cyclobutanones
  作者：Francesco Secci、Stefania Porcu、Carla Aira Rodriguez、Angelo Frongia

  DOI：10.1055/s-0040-1706087

  日期：2021.3

  A general strategy for the synthesis of indolyl cyclobutanones via a tandem Brønsted acid catalyzed 2-hydroxycyclobutanone activation–indole nucleophilic addition has been exploited. The procedure leads to a wide range of 2- and 3-functionalized indole derivatives in good to high yields with broad substrate scope.

  通过串联布朗斯台德酸催化的2-羟基环丁酮活化-吲哚亲核加成反应合成吲哚基环丁酮的一般策略已经被开发出来。该方法导致了范围广泛的2-和3-官能化的吲哚衍生物，具有良好的产率和高的收率，具有广泛的底物范围。
• 2-(1h-indol-3-yl)-2-oxo-acetamides with antitumor activity
  申请人：——

  公开号：US20030158153A1

  公开（公告）日：2003-08-21

  2-(1H-Indol-3-yl)-2-oxo-acetamides having antitumor activity, in particular against solid tumors, more precisely colon and lung tumors, of the following formula I: 1 wherein Y is an oxygen of sulfur atom and X, R 1 , R 2 , R 3 , R 4 and R 5 are as defined in claim 1.

  具有抗肿瘤活性的2-(1H-吲哚-3-基)-2-氧代-乙酰胺，特别针对固体肿瘤，更准确地说是结肠和肺肿瘤，具有以下化学式 I：其中Y为氧或硫原子，X，R1，R2，R3，R4和R5如权利要求1所定义。
• 2-(1h-indol-3-yl)-2-oxo-acetic acid amides with antitumor activity
  申请人：——

  公开号：US20040029858A1

  公开（公告）日：2004-02-12

  2-(III-Indol-3-yl)-2-oxo-acetamide derivatives of formula (I) having antitumor activity in particular against solid tumors, specifically colon and lung tumors. 1

  公式（I）的2-(III-Indol-3-yl)-2-oxo-acetamide衍生物具有抗肿瘤活性，特别是对固体肿瘤，特别是结肠和肺肿瘤。