CAS: 82689-19-8; Boc-Tryptophanol

该化合物是属于氨基酒精类的化学化合物,是氨基酸锥虫的衍生物,在氨基组中含有三丁基羟基碳酸基(BOC)保护组,该组在氨基组中具有乙基-丁基碳酸基(BOC)保护组.这一改变增强了其稳定性和溶解性,使其在peptide合成和其他有机反应中有用.该组一般是白色至非白色固体的,在甲醇和二氯甲烷等有机溶剂中溶解,但水溶解较少.N-BOC-L-Tryptophanol由于结构上类似于tophan,经常用于合成各种生物活性分子和药物,因为其结构上类似于treptophan,这是Serotonin等...

英文名称Boc-Tryptophanol
中文名称Boc-L-色氨醇
IUPAC名称tert-butyl (S)-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate
其它别名Nα-叔丁氧羰基-L-色氨酸醇; α叔丁氧羰基l色氨醇; 1,1-Dimethylethyl[(1S)-2-Hydroxy-1-(1H-Indol-3-Ylmethyl)Ethyl]Carbamate; Tert-Butyl [(2S)-1-Hydroxy-3-(1H-Indol-3-yl)Propan-2-Yl]Carbamate
CAS编号82689-19-8
MFCD编号:MFCD00235953
分子式:C16H22N2O3
分子量:290.36
产品CID: 1816972
产品分类有机原料→分子砌块→芳杂环类化合物→吲哚类化合物

相似结构搜索
InChIKey: JEFQUFUAEKORKL-LBPRGKRZSA-N
InChI=1S/C16H22N2O3/c1-16(2,3)21-15(20)18-12(10-19)8-11-9-17-14-7-5-4-6-13(11)14/h4-7,9,12,17,19H,8,10H2,1-3H3,(H,18,20)/t12-/m0/s1…
计算化学: 氢键受体数3.0氢键供体数3.0可旋转键数4.0

MSDS等安全信息

GHS符号GHS07
警示词Warning
危险描述H302-H315-H319-H335
防范说明P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
UN编号NONH for all modes of transport
危险品标志T+
WGK Germany3

上下游产品

B°C-Trp-OH 21H28N2O6C21H28N2O6 methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate tert-butyl dicarbonatedi-tert-butyl dicarbonateN-tert-butyloxycarbonyl-tryptophanal H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester[1-(3-bromo-phenoxymethyl)-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester H-indol-3-yl)-1-(5-styryl-pyridin-3-yloxymethyl)-ethyl]-carbamic acid tert-butyl ester[2-(1H-indol-3-yl)-1-(5-styryl-pyridin-3-yloxymethyl)-ethyl]-carbamic acid tert-butyl ester H-indol-3-yl)-1-[3-(2-pyridin-4-yl-vinyl)-phenoxymethyl]-ethyl}-carbamic acid tert-butyl ester{2-(1H-indol-3-yl)-1-[3-(2-pyridin-4-yl-vinyl)-phenoxymethyl]-ethyl}-carbamic acid tert-butyl ester

合成工艺路线路线简述

13139-14-5 = 82689-19-8
反应条件:1.1 Reagents: 4-Methylmorpholine Solvents: Tetrahydrofuran; 30 Min,0 °C1.2 Reagents: Methyl Chloroformate; 1 H,0 °C1.3 Reagents: Sodium Borohydride Solvents: Water; 4 H,0 °C
标题:Synthesis And Antimicrobial Activities Of Amides Of Chiral Benzyl Ethers Of N-Boc Protected Aminols Of L-Amino Acids With Succinic Acid
作者:Mumtaz,Salma; Et Al
参考文献:Journal Of The Chemical Society Of Pakistan 日期:2015 卷标:37(2) 页码:407-417]

33900-28-6 = 82689-19-8
反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran; 4 H,0 °C1.2 Reagents: Citric Acid Solvents: Water; > 1 Min
标题:Development Of N-Hydroxycinnamamide-Based Histone Deacetylase Inhibitors With An Indole-Containing Cap Group
作者:Zhang,Yingjie; Et Al
参考文献:Acs Medicinal Chemistry Letters 日期:2013 卷标:4(2) 页码:235-238]

24424-99-5 + 73-22-3 = 82689-19-8
反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran; 4 H,80 °C; 80 °C -> 0 °C1.2 Reagents: Sodium Sulfate Solvents: Water1.3 Solvents: 1,4-Dioxane,Water; 12 H,25 °C
标题:A Catalytic N-Deacylative Alkylation Approach To Hexahydropyrrolo[2,3-B]Indole Alkaloids
作者:Kumar,Nivesh; Et Al
参考文献:Chemical Communications (Cambridge 日期:2018 卷标:54(65) 页码:9083-9086]

24424-99-5 + 73-22-3 = 82689-19-8
反应条件:1.1 Reagents: Thionyl Chloride Solvents: Methanol; 30 Min,0 °C; 18 H,25 °C1.2 Reagents: Triethylamine Solvents: Dichloromethane; 24 H,25 °C1.3 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran; < 0 °C; 4 H,25 °C
标题:Design,Synthesis,And Evaluation Of Novel Akt1 Inhibitors Based On An Indole Scaffold
作者:Yang,Dezhi; Et Al
参考文献:Chemical Biology & Drug Design 日期:2017 卷标:90(5) 页码:791-803]

24424-99-5 + 73-22-3 = 82689-19-8
反应条件:1.1 Reagents: Thionyl Chloride Solvents: Methanol; 30 Min,0 °C; 18 H,Rt1.2 Reagents: Triethylamine Solvents: Dichloromethane; 24 H,25 °C1.3 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran; 0 °C; 4 H,Rt
标题:Design,Synthesis And Evaluation Of Novel Indole Derivatives As Akt Inhibitors
作者:Yang,Dezhi; Et Al
参考文献:Bioorganic & Medicinal Chemistry 日期:2014 卷标:22(1) 页码:366-373]

24424-99-5 + 2899-29-8 = 82689-19-8
反应条件:1.1 Solvents: 1,4-Dioxane,Water; 3 H,Rt
标题:Pseudosymmetry In Azabicyclo[2.1.1]Hexanes. A Stereoselective Construction Of The Bicyclic Core Of Peduncularine
作者:Ragains,Justin R.; Et Al
参考文献:Organic Letters 日期:2006 卷标:8(20) 页码:4437-4440]

73-22-3 = 82689-19-8
反应条件:1.1 Reagents: Thionyl Chloride; 0 °C; Overnight,60 °C2.1 Reagents: Triethylamine Solvents: Dichloromethane; 8 H,Rt3.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran; 4 H,0 °C3.2 Reagents: Citric Acid Solvents: Water; > 1 Min
标题:Development Of N-Hydroxycinnamamide-Based Histone Deacetylase Inhibitors With An Indole-Containing Cap Group
作者:Zhang,Yingjie; Et Al
参考文献:Acs Medicinal Chemistry Letters 日期:2013 卷标:4(2) 页码:235-238]

13139-14-5 = 82689-19-8
反应条件:1.1 Reagents: 4-Methylmorpholine,Isobutyl Chloroformate Solvents: Tetrahydrofuran; 15 Min,-15 °C1.2 Reagents: Sodium Borohydride Solvents: Water; 1 H,-15 °C1.3 Reagents: Water
标题:Synthesis And Evaluation Of Chirally Defined Side Chain Variants Of 7-Chloro-4-Aminoquinoline To Overcome Drug Resistance In Malaria Chemotherapy
作者:Dola,Vasantha Rao; Et Al
参考文献:Antimicrobial Agents And Chemotherapy 日期:2017 卷标:61(3)]

13139-14-5 = 82689-19-8
反应条件:1.1 Reagents: Lithium Chloride,Sodium Borohydride Solvents: Tetrahydrofuran; Overnight,Rt
标题:Synthesis And Binding Properties Of Guanidinium Biscarboxylates
作者:Spaeth,Andreas; Et Al
参考文献:Monatshefte Fuer Chemie 日期:2011 卷标:142(12) 页码:1289-1308]

57229-67-1 = 82689-19-8
反应条件:1.1 Reagents: Lithium Borohydride Catalysts: Methanol Solvents: Tetrahydrofuran; 45 Min,Rt; 45 Min,Rt1.2 Reagents: Ammonium Chloride Solvents: Water; 0 °C
标题:Copper-Catalyzed Cyclization Of Iodo-Tryptophans: A Straightforward Synthesis Of Pyrroloindoles
作者:Coste,Alexis; Et Al
参考文献:Organic Letters 日期:2008 卷标:10(17) 页码:3841-3844]

42290-63-1 = 82689-19-8
反应条件:1.1 Reagents: Iodine,Sodium Borohydride Solvents: Tetrahydrofuran
标题:An Efficient Method For The Reduction Of N-Protected Amino Acids And Peptides To The Corresponding Alcohols
作者:Naqvi,T.; Et Al
参考文献:Journal Of Chemical Research 日期:1999 卷标:(7) 页码:424-425]

24424-99-5 + 7524-52-9 = 82689-19-8
反应条件:1.1 Reagents: Triethylamine Solvents: Dichloromethane; 8 H,Rt2.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran; 4 H,0 °C2.2 Reagents: Citric Acid Solvents: Water; > 1 Min
标题:Development Of N-Hydroxycinnamamide-Based Histone Deacetylase Inhibitors With An Indole-Containing Cap Group
作者:Zhang,Yingjie; Et Al
参考文献:Acs Medicinal Chemistry Letters 日期:2013 卷标:4(2) 页码:235-238]

73-22-3 = 82689-19-8
反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran; 4 H,80 °C; 80 °C -> 0 °C1.2 Reagents: Sodium Sulfate Solvents: Water2.1 Solvents: 1,4-Dioxane,Water; 12 H,25 °C
标题:A Catalytic N-Deacylative Alkylation Approach To Hexahydropyrrolo[2,3-B]Indole Alkaloids
作者:Kumar,Nivesh; Et Al
参考文献:Chemical Communications (Cambridge 日期:2018 卷标:54(65) 页码:9083-9086

L-色氨酸置于lithium Aluminium Tetrahydride,氯化亚砜,三乙胺体系中,用四氢呋喃,二氯甲烷作为反应溶剂,化学反应 4.0H,反应生成 N-α-(叔丁氧基羰基)-L-色氨醇
参考文献:基于吲哚支架的新型akt1抑制剂的设计,合成和评估
标题:基于吲哚支架的新型akt1抑制剂的设计,合成和评估
摘要:设计并合成了一系列针对akt1的新型吲哚衍生物.化合物19B具有70.3%的抑制率表现出最有效的抑制活性对akt1的在10浓度n米和五倍更高的抗增殖活性针对pc-3细胞与ic 50为3.1+/-0.1μ值米比阳性对照(15.5+/-0.4 μ米).
DOI:10.1111/cbdd.13000

海关参考信息

2902200000-苯
2905122000-异丙醇
2905143000-叔丁醇
2912110000-甲醛
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主要参考文献

参考标题:A Facile Synthesis And Crystallographic Analysis Of N-Protected β-Amino Alcohols And Short Peptaibols
作者:Sandip V. Jadhav,Anupam Bandyopadhyay,Sushil N. Benke,Sachitanand M. Mali,Hosahudya N. Gopi
摘要:For The Synthesis Of N-Protected β-Amino Alcohols And Peptaibols Using N-Hydroxysuccinimide Active Esters Is Described. Using This Method, Dipeptide, Tripeptide And Pentapeptide Alcohols Were Isolated In High Yields. The Conformations In Crystals Of β-Amino Alcohol, Dipeptide And Tripeptide Alcohols Were Analysed, With A Well-Defined Type Iii β-Turn Being Observed In The Tripeptide Alcohol Crystals

合成参考文献

参考文献:10.1055/s-0036-1589482
摘要:Gagnon A, Dansereau J, Le Roch A. Organobismuth Reagents: Synthesis, Properties and Applications in Organic Synthesis. Synthesis. 2017 Mar 02;49(08):1707–45. doi: 10.1055/s-0036-1589482.