CAS: 96551-22-3; 1-Boc-3-Hydroxymethylindole

该化合物是有机合成和制药研究中广泛使用的一种受保护的单极衍生物,在温酸条件下,乙型丁氧碳基(Boc)组提供了稳定性和选择性的去保护,使其对多步骤合成具有价值.三点的氢氧甲基替代体为进一步功能化提供了多功能处理器,有利于构建复杂的环环环框架.该化合物在药用化学中对于开发非单极生物活性分子特别有用,在这种分子中,受控的再活性和中间稳定性至关重要.其明确界定的再活性简介确保了合成应用中的再生性.

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上下游产品

CAS号57476-50-3 3-甲酰基-1H-吲哚-1-甲酸叔丁酯 | CAS号338760-26-2 3-甲基-1H-吲哚-1,3-... | CAS号487-89-8 3-吲哚甲醛 | CAS号24424-99-5 二碳酸二叔丁酯 | CAS号700-06-1 3-吲哚甲醇 | CAS号34619-03-9 碳酸二叔丁酯 | CAS号57476-50-3 3-甲酰基-1H-吲哚-1-甲酸叔丁酯 | CAS号96551-21-2 叔丁基3-溴甲基-吲哚-1-羧酸酯 | CAS号114604-96-5 tert-butyl 2-fo...

合成工艺路线路线简述

  • 57476-50-3 = 96551-22-3
    反应条件:1.1 Reagents: Sodium Borohydride Solvents: Methanol; 0 °C; Rt
    标题:A Modular Formal Total Synthesis Of (+/-)-Cycloclavine
    作者:Netz,Natalie; Opatz,Till
    参考文献:Journal Of Organic Chemistry 日期:2016 卷标:81(4) 页码:1723-1730]

    57476-50-3 = 96551-22-3
    反应条件:1.1 Reagents: Sodium Borohydride Solvents: Ethanol; Rt; 16 H,Rt
    标题:Fusarochromene,A Novel Tryptophan-Derived Metabolite From Fusarium Sacchari
    作者:Marshall,James W.; De Mattos-Shipley,Kate M. J.; Ghannam,Iman A. Y.; Munawar,Asifa; Killen,Jonathan C.; Et Al
    参考文献:Organic & Biomolecular Chemistry 日期:2021 卷标:19(1) 页码:182-187]

    57476-50-3 = 96551-22-3
    反应条件:1.1 Reagents: Sodium Borohydride Solvents: Ethanol; Rt; 30 Min,Rt1.2 Reagents: Water
    标题:Pd-Catalyzed Dearomative Carboxylation Of Indolylmethanol Derivatives
    作者:Mita,Tsuyoshi; Ishii,Sho; Higuchi,Yuki; Sato,Yoshihiro
    参考文献:Organic Letters 日期:2018 卷标:20(23) 页码:7603-7606]

    57476-50-3 = 96551-22-3
    反应条件:1.1 Reagents: Sodium Borohydride Solvents: Ethanol; 0 °C; 3 H,Rt
    标题:Phenyl-Urea And Phenyl-Carbamate Derivatives As Inhibitors Of Protein Aggregation
    参考文献:World Intellectual Property Organization]

    57476-50-3 = 96551-22-3
    反应条件:1.1 Reagents: Sodium Borohydride Solvents: Ethanol
    标题:Highly Diastereoselective Alkylation Of A Pyroglutamate Derivative With An Electrophile Obtained From Indole. Synthesis Of A Potential Intermediate For The Preparation Of The Natural Sweetener (-)-Monatin
    作者:De Jesus Oliveira,Davi; Coelho,Fernando
    参考文献:Synthetic Communications 日期:2000 卷标:30(12) 页码:2143-2159]

    57476-50-3 = 96551-22-3
    反应条件:1.1 Reagents: Sodium Borohydride Solvents: Ethanol; < 20 °C; 20 °C -> Rt; 22 H,Rt1.2 Reagents: Sodium Hydroxide Solvents: Water; Rt
    标题:Structure-Enabled Discovery Of A Stapled Peptide Inhibitor To Target The Oncogenic Transcriptional Repressor Tle1
    作者:Mcgrath,Sally; Tortorici,Marcello; Drouin,Ludovic; Solanki,Savade; Vidler,Lewis; Et Al
    参考文献:Chemistry - A European Journal 日期:2017 卷标:23(40) 页码:9577-9584]

    24424-99-5 + 487-89-8 = 96551-22-3
    反应条件:1.1 Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dichloromethane; 30 Min,0 °C; 30 Min,Rt1.2 Reagents: Sodium Borohydride Solvents: Methanol,Dichloromethane; 10 Min,0 °C; 15 Min,0 °C; 2 H,Rt1.3 Reagents: Hydrochloric Acid Solvents: Diethyl Ether,Water; 0 °C
    标题:Formamide-Catalyzed Nucleophilic Substitutions: Mechanistic Insight And Rationalization Of Catalytic Activity
    作者:Kohlmeyer,Corinna; Schaefer,Andre; Huy,Peter H.; Hilt,Gerhard
    参考文献:Acs Catalysis 日期:2020 卷标:10(19) 页码:11567-11577]

    57476-50-3 = 96551-22-3
    反应条件:1.1 Reagents: Sodium Borohydride Solvents: Methanol; 1.5 H,Rt
    标题:Synthesis And Biological Evaluation Of Hapten-Clicked Analogues Of The Antigenic Peptide Melan-A/mart-126(27L)-35
    作者:Tarbe,Marion; Miles,John J.; Edwards,Emily S. J.; Miles,Kim M.; Sewell,Andrew K.; Et Al
    参考文献:Chemmedchem 日期:2020 卷标:15(9) 页码:799-807]

    57476-50-3 = 96551-22-3
    反应条件:1.1 Reagents: Sodium Borohydride Solvents: Ethanol
    标题:Concise Synthesis Of (2R,4R)-Monatin
    作者:Amino,Yusuke
    参考文献:Chemical & Pharmaceutical Bulletin 日期:2016 卷标:64(8) 页码:1242-1247]

    57476-50-3 = 96551-22-3
    反应条件:1.1 Reagents: Sodium Borohydride Solvents: Methanol; 20 Min,0 °C; 4 H,Rt1.2 Reagents: Water; 15 Min,Rt
    标题:Synthesis And Cytotoxic Activity Of Novel 1-((Indol-3-Yl)Methyl)-1H-Imidazolium Salts
    作者:Xu,Xiao-Liang; Wang,Jia; Yu,Chun-Lei; Chen,Wen; Li,Ying-Chao; Et Al
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2014 卷标:24(21) 页码:4926-4930]

    945679-27-6 = 96551-22-3
    反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran; 0 °C; 0 °C -> 25 °C; 20 Min,25 °C1.2 Reagents: Ammonium Chloride Solvents: Water; 25 °C
    标题:Reduction Of 1-Pyrrolyl And 1-Indolyl Carbamates To Hemiaminals
    作者:Hsu,He-Chu; Hou,Duen-Ren
    参考文献:Tetrahedron Letters 日期:2009 卷标:50(51) 页码:7169-7171]

    57476-50-3 = 96551-22-3
    反应条件:1.1 Reagents: Sodium Borohydride Solvents: Ethanol; 18 H,Rt
    标题:Highly Active,Immobilized Ruthenium Catalysts For Oxidation Of Alcohols To Aldehydes And Ketones. Preparation And Use In Both Batch And Flow Systems
    作者:Kobayashi,Shu; Miyamura,Hiroyuki; Akiyama,Ryo; Ishida,Tasuku
    参考文献:Journal Of The American Chemical Society 日期:2005 卷标:127(25) 页码:9251-9254]

    57476-50-3 = 96551-22-3
    反应条件:1.1 Reagents: Sodium Borohydride
    标题:Synthesis Of Kurasoin B Using Phase-Transfer-Catalyzed Acylimidazole Alkylation
    作者:Christiansen,Michael A.; Butler,Aaron W.; Hill,Amanda R.; Andrus,Merritt B.
    参考文献:Synlett 日期:2009 卷标:(4) 页码:653-657]

    57476-50-3 = 96551-22-3
    反应条件:1.1 Reagents: Sodium Borohydride Solvents: Ethanol; 30 Min,Rt
    标题:3-O And 2-C Alkylation Of L-Ascorbates With Benzyl Halides And N-Substituted Indolemethanol Derivatives
    作者:Korolev,A. M.; Luzikov,Yu. N.; Reznikova,M. I.; Preobrazhenskaya,M. N.
    参考文献:Russian Chemical Bulletin 日期:2010 卷标:59(2) 页码:457-462
📜吲哚-3-甲醇置于咪唑,盐酸,4-二甲氨基吡啶体系中,用 甲醇,N,N-二甲基甲酰胺,乙腈 作为反应溶剂,化学反应 2.17H,反应生成 3-羟基甲基吲哚-1-羧酸叔丁酯
参考文献:串联n-烷基化-Aza-Cope重排反应在吲哚中轻松安装2-反向异戊烯基官能团及其在合成中的应用
标题:串联n-烷基化-Aza-Cope重排反应在吲哚中轻松安装2-反向异戊烯基官能团及其在合成中的应用
摘要:描述了空前的串联n-烷基化-离子氮杂-Cope(或claisen)重排-水解反应,该反应容易得到的吲哚基溴化物与烯胺类化合物.由于这两个过程的复杂性,已经发现了操作上简单的n-烷基化和随后的微波辐照离子氮杂-Cope重排-水解过程.串联反应是高效制备合成和生物学上重要但有挑战性的2-反向季铵中心的烯丙基化吲哚的有力方法.值得注意的是,非寻常的非芳香族3-亚甲基-2,3-二氢-1 H产生了吲哚结构,而不是芳香族吲哚.此外,Aza-Cope重排反应在区域上具有很高的选择性,从而产生了以季中心为中心的异戊二烯基官能团,该官能团通常通过报道的方法产生两种区域异构体的混合物.合成的非芳族3-亚甲基-2,3-二氢-1H-吲哚结构的合成值已被证明是有效合成结构多样的2-反向炔丙基化吲哚(如二氢吲哚,吲哚稠合的杜邦)的通用组成部分.和内酰胺,以及天然产物布鲁索林d.
DOI:10.1002/chem.201503355

海关参考信息

专利信息


专利号:US-5554753-A
优先权日:1993-08-25
标 题:Catalytic enantioselective synthesis of α-amino acid derivatives by phase-transfer catalysis
发明人：O'DONNELL MARTIN J; WU SHENGDE; ESIKOVA IRENA; MI AIQIAO
权利人:INDIANA UNIVERSITY FOUNDATION
摘要:Described are improved processes for the enantioselective synthesis of α-amino acids which involve combinations of solvents, highly-mixed and low-temperature reaction conditions, and novel catalysts. Also described are novel catalysts and precursors to α-amino acid derivatives.

专利号:WO-9506029-A1
优先权日:1993-08-25
标 题:Enantioselective synthesis of alpha - alkylated amino acid derivatives by phase - transfer catalysis

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合成参考文献


参考文献:10.1055/s-0036-1591315
摘要:Synthesis of Furan and Pyrrole Derivatives by Oxetane Ring Opening. Synfacts. 2017 Sep 18;13(10):1025. doi: 10.1055/s-0036-1591315.
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