2-[N-methyl-N-(2-pyridyl)amino]-1-phenylethanol | 1215-44-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-[N-methyl-N-(2-pyridyl)amino]-1-phenylethanol
• 英文别名: (±)-2-[N-methyl-N-(pyridin-2-yl)amino]-1-phenylethanol；2-(N-(β-Hydroxyphenethyl)methylamino)pyridin；2-(methyl-[2]pyridyl-amino)-1-phenyl-ethanol；2-(Methyl-[2]pyridyl-amino)-1-phenyl-aethanol；2-[Methyl(pyridin-2-yl)amino]-1-phenylethanol
• CAS: 1215-44-7
• 化学式: C₁₄H₁₆N₂O
• 分子量: 228.294
• InChiKey: HJRBVHHDLAJXLD-UHFFFAOYSA-N

物化性质

• 沸点：
  147-157 °C(Press: 0.2 Torr)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  36.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[N-methyl-N-(2-pyridyl)amino]-1-phenylethanol 以 乙腈 为溶剂， 反应 2.75h， 生成 8-amino-1-methyl-3-phenyl-2,3-dihydro-1H-pyrido[1,2-b][1,2,4]oxadiazin-5-ium chloride
  参考文献：
  名称：

  Modulating the Stability of 2-Pyridinyl Thermolabile Hydroxyl Protecting Groups via the “Chemical Switch” Approach

  摘要：

  A novel and effective method is presented for modulating the stability of 2-Pyridinyl Thermolabile Protecting Groups (2-Py TPGs) in the "chemical switch" approach. The main advantage of the discussed approach is the possibility of changing the nudeophilic character of pyridine nitrogen using different switchable factors, which results in an increase or decrease in the thermal deprotection rate. One of the factors is transformation of a nitro into an amine group via reduction with a low-valent titanium in mild conditions. The usefulness of our approach is corroborated using 3'-O-acetyl nucleosides as model compounds. Their stability in various solvents and temperatures before and after reduction is also examined. Pyridine N-oxide and pH are other factors responsible for the nudeophilicity and stability of 2-Pyridinyl Thermolabile Protecting Groups in thermal deprotection. Protonation of 4-amino 2-Pyridinyl Thermolabile Protecting Groups is demonstrated by H-1-N-15 HMBC and HSQC NMR analysis.

  DOI：

  10.1021/acs.joc.5b02033
• 作为产物：
  描述：

  2-二甲氨基吡啶 、 苯甲醛 反应 24.0h， 以47%的产率得到2-[N-methyl-N-(2-pyridyl)amino]-1-phenylethanol
  参考文献：
  名称：

  直接照射N，N-二甲基苯胺中的羰基化合物制备乙醇胺的简便方法。

  摘要：

  在不使用溶剂的情况下，用300 nm紫外光直接照射N，N-二甲基苯胺中的某些羰基化合物，可以以中等收率得到乙醇胺作为主要产物。

  DOI：

  10.1016/s0040-4039(01)01784-1

文献信息

• Thermolytic Carbonates for Potential 5‘-Hydroxyl Protection of Deoxyribonucleosides
  作者：Marcin K. Chmielewski、Vicente Marchán、Jacek Cieślak、Andrzej Grajkowski、Victor Livengood、Ursula Münch、Andrzej Wilk、Serge L. Beaucage

  DOI：10.1021/jo035089g

  日期：2003.12.1

  Thermolytic groups structurally related to well-studied heat-sensitive phosphate/thiophosphate protecting groups have been evaluated for 5'-hydroxyl protection of deoxyribonucleosides as carbonates and for potential use in solid-phase oligonucleotide synthesis. The spatial arrangement of selected functional groups forming an asymmetric nucleosidic 5'-O-carbonic acid ester has been designed to enable heat-induced cyclodecarbonation reactions, which would result in the release of carbon dioxide and the generation of a nucleosidic 5'-hydroxyl group. The nucleosidic 5'-O-carbonates 3-8, 10-15, and 19-21 were prepared and were isolated in yields ranging from 45 to 83%. Thermolytic deprotection of these carbonates is preferably performed in aqueous organic solvent at 90 degreesC under near neutral conditions. The rates of carbonate deprotection are dependent on the nucleophilicity of the functional group involved in the postulated cyclodecarbonation reaction and on solvent polarity. Deprotection kinetics increase according to the following order: 4 < 5 < 10 < 6 < 12 < 7 < 13 < 8 < 14 congruent to 19-21 and CCl4 < dioxane < MeCN < t-BuOH < MeCN:phosphate buffer (3:1 v/v, pH 7.0) < EtOH:phosphate buffer (1:1 v/v, pH 7.0). Complete thermolytic deprotection of carbonates 7, 8, 13, and 14 is achieved within 20 min to 2 h under optimal conditions in phosphate buffer-MeCN. The 2-(2-pyridyl)amino-1-phenylethyl and 2-[N-methyl-N-(2-pyridyl)]aminoethyl groups are particularly promising for 5'-hydroxyl protection of deoxyribonucleosides as thermolytic carbonates.
• Aminopyridines. II. The Preparation and Properties of 2-(Hydroxyalkylamino)-pyridines¹
  作者：Allan P. Gray、Donald E. Heitmeier、Ernest E. Spinner

  DOI：10.1021/ja01525a062

  日期：1959.8
• Thermolabile hydroxyl protecting groups and methods of use
  申请人：Beaucage L. Serge

  公开号：US20060281911A1

  公开（公告）日：2006-12-14

  Provided is a hydroxyl-protected alcohol comprising a thermolabile hydroxyl-protecting group comprising a 2-pyridyl substituent and a precursor of the thermolabile hydroxyl-protected alcohol. An exemplary thermolabile hydroxyl-protected alcohol is represented by the formula Pg-O—R, wherein Pg is a protecting group of the formula: (Formula) wherein: A is a 2-pyridyl; Z is CH 2 or NR 1 ; R 1 , R 2 , R 2′ , R 3 and R 3′ are the same or different and each can be, e.g., H, alkyl, or alkyl comprising an aryl substituent; W is CO, CS, or SO; and R is the organic residue of the hydroxyl-protected alcohol. Also provided is a method of producing an alcohol, which method comprises heating the hydroxyl-protected alcohol, which optionally may be obtained from a precursor, at a temperature effective to cleave the hydroxyl-protecting group. The method can be used to produce oligonucleotides.
• US7612197B2
  申请人：——

  公开号：US7612197B2

  公开（公告）日：2009-11-03
• [EN] THERMOLABILE HYDROXYL PROTECTING GROUPS AND METHODS OF USE<br/>[FR] GROUPES PROTECTEURS HYDROXYLE THERMOLABILES ET LEURS PROCEDES D'UTILISATION
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2004101582A2

  公开（公告）日：2004-11-25

  Provided is a hydroxyl-protected alcohol comprising a thermolabile hydroxyl-protecting group comprising a 2-pyridyl substituent and a precursor of the thermolabile hydroxyl-protected alcohol. An exemplary thermolabile hydroxyl-protected alcohol is represented by the formula Pg-O-R, wherein Pg is a protecting group of the formula : (Formula) wherein : A is a 2-pyridyl; Z is CH2 or NR1; R1, R2, R2', R3 and R3' are the same or different and each can be, e.g., H, alkyl, or alkyl comprising an aryl substituent; W is CO, CS, or SO; and R is the organic residue of the hydroxyl-protected alcohol. Also provided is a method of producing an alcohol, which method comprises heating the hydroxyl-protected alcohol, which optionally may be obtained from a precursor, at a temperature effective to cleave the hydroxyl-protecting group. The method can be used to produce oligonucleotides.