6-(2'-hydroxy-2'-phenylethyl)-2,3,4,5-tetrahydropyridine | 127983-45-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 6-(2'-hydroxy-2'-phenylethyl)-2,3,4,5-tetrahydropyridine
• 英文别名: 2-(1-oxido-2,3,4,5-tetrahydropyridin-1-ium-6-yl)-1-phenylethanol
• CAS: 127983-45-3
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: IQIKOBYFSVNDCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6-(2'-hydroxy-2'-phenylethyl)-2,3,4,5-tetrahydropyridine 在 sodium tetrahydroborate 、 mercury(II) oxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (S)-2-((R)-1-Oxy-2,3,4,5-tetrahydro-pyridin-2-yl)-1-phenyl-ethanol
  参考文献：
  名称：

  Ali, Sk. Asrof, Journal of Chemical Research, Miniprint, 1994, # 2, p. 301 - 317

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-2-((R)-1-Oxy-2,3,4,5-tetrahydro-pyridin-2-yl)-1-phenyl-ethanol 在 sodium tetrahydroborate 、 mercury(II) oxide 作用下， 以 二氯甲烷 为溶剂， 生成 6-(2'-hydroxy-2'-phenylethyl)-2,3,4,5-tetrahydropyridine
  参考文献：
  名称：

  Peracid induced ring opening of isoxazolidines. A mechanistic study.

  摘要：

  Conformational analysis and mechanistic study of peracid induced ring opening of several isoxazolidines have been carried out. The orientation of the nitrogen lone pair dictates the regiochemistry of the ring opening which involves an intramolecular kinetic deprotonation of a nitroxonium ion intermediate.

  DOI：

  10.1016/s0040-4039(00)79856-x

文献信息

• Nitrone cycloadditions: synthesis of (±)-andrachamine
  作者：William Carruthers、Peter Coggins、John B. Weston

  DOI：10.1039/p19900002323

  日期：——

  The usefulness of the cycloaddition of alkenes to 2-alkyl-2,3,4,5-tetrahydropyridine oxides for the preparation of trans-2,6-dialkylpiperidines is confirmed by a stereoselective synthesis of (±)-andrachamine. Peroxy acid oxidation of 9-oxa-1-azabicyclo[4.3.0]nonanes does not lead regioselectively to the corresponding 2-alkyl-2,3,4,5-tetrahydropyridine oxide, as had previously been claimed.

  通过（±）-andrachamine的立体选择性合成，证实了将烯烃环加成至2-烷基-2,3,4,5-四氢吡啶氧化物上以制备反式-2,6-二烷基哌啶。如先前所主张的，9-氧杂-1-氮杂双环[4.3.0]壬烷的过氧酸氧化不会选择性地导致相应的2-烷基-2,3,4,5-四氢吡啶氧化物。
• Nitrone cycloaddition: peroxy acid oxidation of 2-phenyl-1-oxa-9-azabicyclo[4.3.0]nonane
  作者：William Carruthers、Peter Coggins、John B. Weston

  DOI：10.1039/c39900000091

  日期：——

  Oxidation of 2-phenyl-1-oxa-9-azabicyclo[4.3.0]nonane (5) with m-chloroperoxybenzoic acid is not regioselective, in contrast to the case with the corresponding 1-oxa-8-azabicyclo[3.3.0]octane (2; n= 1, R1= H, R2= Ph), affording mainly the keto-nitrone (7). On reaction with styrene in boiling toluene the latter forms the oxabicyclononane (9).

  2-苯基-1-氧杂-9-氮杂双环[4.3.0]壬烷（氧化5）用米氯过氧酸不是区域选择性的，相反的情况下与相应的1-氧杂-8-氮杂双环[3.3.0 ]辛烷（2；n = 1，R 1 = H，R 2 = Ph），主要得到酮-硝基（7）。在沸腾的甲苯中与苯乙烯反应后，后者形成氧杂双环壬烷（9）。
• Nitrone cycloaddition : peracid oxidation of perhydro-1,2-oxazolo[3,2-c][1,4]oxazines
  作者：Sk.Asrof Ali、Hasan A. Al-Muallem

  DOI：10.1016/s0040-4020(01)87213-6

  日期：1993.8

  2-oxazolo[3,2-c][1,4]oxazines (2) and (6) in aprotic solvent is dictated by orientation of lone pair of electrons on nitrogen. In contrast to the case with the corresponding hexahydro-2H-isoxazolo[2,3-a]pyridines (17), the oxidation of (2) gives mainly an equilibrium mixture of aldonitrone (3) and its hydroxylamine tautomer (4) which undergo stereoselective cycloaddition with styrene and methyl methacrylate

  过酸诱导的过氢-1,2-恶唑并[3,2-c] [1,4]恶嗪（2）和（6）在质子惰性溶剂中的开环反应是由孤对电子在氮上的取向决定的。与相应的六氢-2H-异恶唑并[2,3-a]吡啶（17）的情况相反，（2）的氧化主要生成醛亚硝基（3）及其羟胺互变异构体（4）的平衡混合物，与苯乙烯和甲基丙烯酸甲酯的立体选择性环加成反应。X射线衍射研究表明（2）中的6-5环系统是顺式稠合的。
• Mercury(II) oxide oxidation of 2-substituted-N-hydroxypiperidine: A solution to the regiochemical problem
  作者：Sk. Asrof Ali

  DOI：10.1016/s0040-4039(00)73986-4

  日期：1993.8
• CARRUTHERS, WILLIAM;COGGINS, PETER;WESTON, JOHN B., J. CHEM. SOC. CHEM. COMMUN.,(1990) N, C. 91-92
  作者：CARRUTHERS, WILLIAM、COGGINS, PETER、WESTON, JOHN B.

  DOI：——

  日期：——