2-[bis(2-hydroxyethyl)amino]-2-phenyl-1-ethanol | 85141-89-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-[bis(2-hydroxyethyl)amino]-2-phenyl-1-ethanol
• 英文别名: 2-[Bis(2-hydroxyethyl)amino]-2-phenylethanol
• CAS: 85141-89-5
• 化学式: C₁₂H₁₉NO₃
• 分子量: 225.288
• InChiKey: GJJPPOAKKISSJD-UHFFFAOYSA-N

物化性质

• 沸点：
  416.6±35.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[bis(2-hydroxyethyl)amino]-2-phenyl-1-ethanol 以 氘代乙腈 为溶剂， 生成 (CH₂CH₂O)2NHBCH₂CH(C₆H₅)O⁽¹⁺⁾*CF₃SO₃^(1-)=(CH₂CH₂O)2NHBCH₂CH(C₆H₅)O(CF₃SO₃)
  参考文献：
  名称：

  芳香族笼中具有苯基取代基的金属戊烷的合成与表征

  摘要：

  摘要一系列新的单和二苯基取代的甲硅烷基和硼烷烃N（CH2CH2O）2（CHR3CR1R2O）MZ（M = Si，Z = CH2Cl，C CPh，H，OMenth，R1，R2，R3 = H，Ph; M = B ，Z ＝无，R 1，R 2，R 3 ＝ H，Ph）已经合成。既进行了烷氧基化反应又对预先形成的金属latrane骨架进行了逐步修饰。氯甲基衍生物N（CH2CH2O）2（CHRCHRO）SiCH2Cl（R = H，Ph）在分子内循环膨胀下与叔丁基醚反应，得到1-叔丁氧基-2-氨基-3-氧杂亚杂环戊酸酯N（CH2CH2O）（CH2CH2OCH2） （CHRCHRO）SiOtBu（R = H，Ph）。用三氟甲磺酸和三氟甲磺酸三甲基甲硅烷基酯处理硼烷烃N（CH2CH2O）2（CH2CR1R2O）B（R1，R2 = H，Ph）会导致氮原子上发生亲电进攻的产物。

  DOI：

  10.1016/j.ica.2006.07.109
• 作为产物：
  描述：

  氧化苯乙烯 、 二乙醇胺 反应 4.0h， 生成 2-amino-1-phenylethanol 、 2-[bis(2-hydroxyethyl)amino]-2-phenyl-1-ethanol
  参考文献：
  名称：

  Synthesis and characterization of 3- and 4-phenylgermatranes: X-ray crystal structures of N(CH2CH2O)2(CH2CHPhO)GeZ (Z=F, OSiMe3, CCPh) and N(CH2CH2O)2(CHPhCH2O)GeOH

  摘要：

  Reaction of excess of product A [(HOCH2CH2)(2)NCH2CH(Ph)OH (1):(HOCH2CH2)(2)NCH(Ph)CH2OH (2) = 9:1] with GeCl4 led to a mixture of 1-chloro-3-phenylgermatrane (3) and 1-chloro-4-phenylgermatrane (4). Compound 4 was isolated in yield 9% from this mixture. Reaction of (EtO)(3)GeCl with product A gave 3 in yield 55%. 1-(Phenylethynyl)-3-phenylgermatrane (5) was prepared in yield 31% by treatment of (EtO)(3)GeCdropCPh with product A. Reaction of product A with mixture of GeO2 and H2O produced N(CH2CH2O)(2)(CH2CHPhO)GeOH (6) in yield 73%. The presence of N(CH2CH2O)(2)(CHPhCH2O)GeOH (7) among the products of this reaction was confirmed by H-1-, C-13-NMR spectroscopy and X-ray analysis. N(CH2CH2O)(2)(CH2CHPhO)GeF (8) is formed by the treatment of 6 with BF3 . Et2O. N(CH2CH2O)(2)(CH2CHPhO)GeOSiMe3 (9) was obtained by silylation of 6 with (Me3Si)(2)NH or Me3SiCl-Et3N. Refluxing of a suspension of 6 in xylene with continuous removal of water by azeotropic distillation afforded [N(CH2CH2O)(2)(CH(2)CHPh0)Ge](2)O (10). 9 reacted with SOCl2, Me3SiBr and Me3SiOTf to give N(CH2CH2O)(2)(CH2CHPhO)GeX (3, X = Cl; 11, X = Br; 12, X = OTf), respectively. Reaction of 11 with Et3SnOMe led to the formation of N(CH2CH2O)(2)(CH2CHPhO)GeO e (13). Germatranes N(CH2CH2O)(2)(CH2CHPhO)GeY [14, Y = Flu (fluorenyl); 15, Y = N(SiMe3)(2)] were obtained from the nucleophilic substitution of the substituent X in N(CH2CH2O)(2)(CH2CHPhO)GeX (X = OSiMe3, Br) with the corresponding LiY. All compounds were characterized by H-1- and C-13-NMR spectroscopy and mass spectrometry. Single-crystal structures of 5 and 7-9 were determined by X-ray diffraction studies. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00225-0

文献信息

• Synthesis and characterization of metallatranes with phenyl substituents in atrane cage
  作者：Sergey S. Karlov、Anastasia A. Selina、Eleonora S. Chernyshova、Yuri F. Oprunenko、Alexei A. Merkulov、Victor A. Tafeenko、Andrei V. Churakov、Judith A.K. Howard、Galina S. Zaitseva

  DOI：10.1016/j.ica.2006.07.109

  日期：2007.2

  N(CH2CH2O)2(CHR3CR1R2O)MZ (M = Si, Z = CH2Cl, C CPh, H, OMenth, R1, R2, R3 = H, Ph; M = B, Z = nothing, R1, R2, R3 = H, Ph) have been synthesized. Both transalkoxylation and stepwise modification of a preformed metallatrane skeleton were used. The chloromethyl derivatives N(CH2CH2O)2(CHRCHRO)SiCH2Cl (R = H, Ph) react with tert-BuOK under intramolecular cycle expansion to give 1-tert-butoxy-2-carba-3-oxahomosilatranes

  摘要一系列新的单和二苯基取代的甲硅烷基和硼烷烃N（CH2CH2O）2（CHR3CR1R2O）MZ（M = Si，Z = CH2Cl，C CPh，H，OMenth，R1，R2，R3 = H，Ph; M = B ，Z ＝无，R 1，R 2，R 3 ＝ H，Ph）已经合成。既进行了烷氧基化反应又对预先形成的金属latrane骨架进行了逐步修饰。氯甲基衍生物N（CH2CH2O）2（CHRCHRO）SiCH2Cl（R = H，Ph）在分子内循环膨胀下与叔丁基醚反应，得到1-叔丁氧基-2-氨基-3-氧杂亚杂环戊酸酯N（CH2CH2O）（CH2CH2OCH2） （CHRCHRO）SiOtBu（R = H，Ph）。用三氟甲磺酸和三氟甲磺酸三甲基甲硅烷基酯处理硼烷烃N（CH2CH2O）2（CH2CR1R2O）B（R1，R2 = H，Ph）会导致氮原子上发生亲电进攻的产物。
• Synthesis and characterization of 3- and 4-phenylgermatranes: X-ray crystal structures of N(CH2CH2O)2(CH2CHPhO)GeZ (Z=F, OSiMe3, CCPh) and N(CH2CH2O)2(CHPhCH2O)GeOH
  作者：Ekaterina V. Gauchenova、Sergey S. Karlov、Anastasia A. Selina、Eleonora S. Chernyshova、Andrei V. Churakov、Judith A.K. Howard、Nikolaj A. Troitsky、Stanislav N. Tandura、Jörg Lorberth、Galina S. Zaitseva

  DOI：10.1016/s0022-328x(03)00225-0

  日期：2003.6

  Reaction of excess of product A [(HOCH2CH2)(2)NCH2CH(Ph)OH (1):(HOCH2CH2)(2)NCH(Ph)CH2OH (2) = 9:1] with GeCl4 led to a mixture of 1-chloro-3-phenylgermatrane (3) and 1-chloro-4-phenylgermatrane (4). Compound 4 was isolated in yield 9% from this mixture. Reaction of (EtO)(3)GeCl with product A gave 3 in yield 55%. 1-(Phenylethynyl)-3-phenylgermatrane (5) was prepared in yield 31% by treatment of (EtO)(3)GeCdropCPh with product A. Reaction of product A with mixture of GeO2 and H2O produced N(CH2CH2O)(2)(CH2CHPhO)GeOH (6) in yield 73%. The presence of N(CH2CH2O)(2)(CHPhCH2O)GeOH (7) among the products of this reaction was confirmed by H-1-, C-13-NMR spectroscopy and X-ray analysis. N(CH2CH2O)(2)(CH2CHPhO)GeF (8) is formed by the treatment of 6 with BF3 . Et2O. N(CH2CH2O)(2)(CH2CHPhO)GeOSiMe3 (9) was obtained by silylation of 6 with (Me3Si)(2)NH or Me3SiCl-Et3N. Refluxing of a suspension of 6 in xylene with continuous removal of water by azeotropic distillation afforded [N(CH2CH2O)(2)(CH(2)CHPh0)Ge](2)O (10). 9 reacted with SOCl2, Me3SiBr and Me3SiOTf to give N(CH2CH2O)(2)(CH2CHPhO)GeX (3, X = Cl; 11, X = Br; 12, X = OTf), respectively. Reaction of 11 with Et3SnOMe led to the formation of N(CH2CH2O)(2)(CH2CHPhO)GeO e (13). Germatranes N(CH2CH2O)(2)(CH2CHPhO)GeY [14, Y = Flu (fluorenyl); 15, Y = N(SiMe3)(2)] were obtained from the nucleophilic substitution of the substituent X in N(CH2CH2O)(2)(CH2CHPhO)GeX (X = OSiMe3, Br) with the corresponding LiY. All compounds were characterized by H-1- and C-13-NMR spectroscopy and mass spectrometry. Single-crystal structures of 5 and 7-9 were determined by X-ray diffraction studies. (C) 2003 Elsevier Science B.V. All rights reserved.