(+)-(2R,2'R,2''R)-triphenylethan-2-olamine | 156317-12-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (+)-(2R,2'R,2''R)-triphenylethan-2-olamine
• 英文别名: (R,R,R)-tris(2-phenyl)ethanolamine；N,N,N-tris((R)-phenylethanol)amine；(1R)-2-[bis[(2R)-2-hydroxy-2-phenylethyl]amino]-1-phenylethanol
• CAS: 156317-12-3
• 化学式: C₂₄H₂₇NO₃
• 分子量: 377.483
• InChiKey: LLIFRAVJIJSSCA-HJOGWXRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2,2'-bipyridine-5-carbonyl chloride 、 (+)-(2R,2'R,2''R)-triphenylethan-2-olamine 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 [(1R)-2-[bis[(2R)-2-phenyl-2-(6-pyridin-2-ylpyridine-3-carbonyl)oxyethyl]amino]-1-phenylethyl] 6-pyridin-2-ylpyridine-3-carboxylate
  参考文献：
  名称：

  Enantiomeric programming in tripodal transition metal scaffolds

  摘要：

  分离对映体纯三螯合物 (Δ/Λ)-fac-[Ru(L1)3]2+ 的新途径 （其中L1是2,2'-联吡啶-5-羧酸）被证明，其中过渡金属中心保留了用于控制金属中心几何结构的简单三足系绳中存在的手性记忆。

  DOI：

  10.1039/b703761a
• 作为产物：
  描述：

  (R)-环氧苯乙烷 在 甲醇 、 氨 作用下， 反应 120.0h， 以18%的产率得到(+)-(2R,2'R,2''R)-triphenylethan-2-olamine
  参考文献：
  名称：

  Early Transition Metal Alkoxide Complexes Bearing Homochiral Trialkanolamine Ligands

  摘要：

  Enantiomerically pure trialkanolamines of the formula N(CH(2)CHROH)(3), where R = methyl (3a), cyclohexyl (3b), tert-butyl (3c), or phenyl (3d), are readily synthesized by the reaction of ammonia with 3 equiv of an enantiopure epoxide. Trialkanolamines 3a-d replace n-propanol in tri-n-propyl vanadate to afford corresponding complexes 4a-d of the formula LV=O, where L is the deprotonated trialkanolamine. Similarly, (S,S,S)-triisopropanolamine 3a reacts with Ti((OPr)-Pr-i)(4) to produce monomeric LTi((OPr)-Pr-i), 7a, which upon treatment with acetyl chloride gives the chloro complex LTiCl, 7b. The later group 5 ethoxides react with 3a to produce LM(OEt)(2) (M = Nb, Ta). Partial hydrolysis of the Nb and Ta derivatives produces tetrameric mu-oxo-bridged structures which retain the trialkanolamine ligands. In all complexes the transition metal resides in a highly asymmetric environment, suggesting that this class of complexes may find use in the field of asymmetric catalysis. The X-ray crystal structures of complexes 4c and 7b are reported.

  DOI：

  10.1021/ja00093a011
• 作为试剂：
  描述：

  叔丁基硫基苯 在 titanium(IV) isopropylate 、 过氧化氢异丙苯 、 (+)-(2R,2'R,2''R)-triphenylethan-2-olamine 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 (tert-butylsulfinyl)benzene 、 tert-butyl-phenyl sulfone 、 (S)-(-)-(tert-butylsulfinyl)benzene
  参考文献：
  名称：

  Enantioselective Titanium-Catalyzed Sulfides Oxidation:  Novel Ligands Provide Significantly Improved Catalyst Life

  摘要：

  DOI：

  10.1021/jo960359z

文献信息

• Use of electrospray ionization mass spectrometry to characterize chiral reactive intermediates in a titanium alkoxide mediated sulfoxidation reaction
  作者：Marcella Bonchio、Giulia Licini、Giorgio Modena、Stefano Moro、Olga Bortolini、Piero Traldi、William A. Nugent

  DOI：10.1039/a701227f

  日期：——

  The ESIMS technique, combined with 1 H NMR evidence, provides a precise inventory of the catalytic Ti IV precursors and the characterization of the reactive peroxometal complex involved in enantioselective sulfoxidation employing the Ti IV –homochiral trialkanolamine–alkylhydroperoxide system.

  ESIMS 技术与 1 H NMR 证据相结合，提供了催化 Ti IV 前体的精确清单，并描述了采用 Ti IV - 同手性三烷醇胺 - 烷基过氧化氢体系进行对映选择性硫氧化作用时所涉及的活性过氧金属复合物的特征。
• Early Transition Metal Alkoxide Complexes Bearing Homochiral Trialkanolamine Ligands
  作者：William A. Nugent、Richard L. Harlow

  DOI：10.1021/ja00093a011

  日期：1994.7

  Enantiomerically pure trialkanolamines of the formula N(CH(2)CHROH)(3), where R = methyl (3a), cyclohexyl (3b), tert-butyl (3c), or phenyl (3d), are readily synthesized by the reaction of ammonia with 3 equiv of an enantiopure epoxide. Trialkanolamines 3a-d replace n-propanol in tri-n-propyl vanadate to afford corresponding complexes 4a-d of the formula LV=O, where L is the deprotonated trialkanolamine. Similarly, (S,S,S)-triisopropanolamine 3a reacts with Ti((OPr)-Pr-i)(4) to produce monomeric LTi((OPr)-Pr-i), 7a, which upon treatment with acetyl chloride gives the chloro complex LTiCl, 7b. The later group 5 ethoxides react with 3a to produce LM(OEt)(2) (M = Nb, Ta). Partial hydrolysis of the Nb and Ta derivatives produces tetrameric mu-oxo-bridged structures which retain the trialkanolamine ligands. In all complexes the transition metal resides in a highly asymmetric environment, suggesting that this class of complexes may find use in the field of asymmetric catalysis. The X-ray crystal structures of complexes 4c and 7b are reported.
• Syndiotactic polystyrene with very high molecular weight produced by sterically and electronically modified catalyst
  作者：Youngjo Kim、Youngkyu Do

  DOI：10.1016/s0022-328x(02)01555-3

  日期：2002.8

  A new type of the half-metallocene catalysts for the syndiospecific polymerization of styrene was prepared by the reaction of various kinds of trialkanolamine with Cp*TiCl3 in the presence of triethylamine. All seven compounds have a highly thermal stability and they show fairly good activities in the presence of cocatalyst MMAO in styrene polymerization. Especially, highly bulky and electronically deficient 7/MMAO system affords syndiotactic polystyrene with very high molecular weight. (C) 2002 Published by Elsevier Science B.V.
• Highly regioselective microwave-assisted synthesis of enantiopure C3-symmetric trialkanolamines
  作者：Laura Favretto、William A. Nugent、Giulia Licini

  DOI：10.1016/s0040-4039(02)00306-4

  日期：2002.4

  Enantiopure, C-3-symmetric trialkanolamines can be efficiently and rapidly obtained on a gram scale via one pot or step-wise microwave-assisted epoxide ring opening with ammonia in high yields (up to 89%) and regioselectivity up to 100%. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Enantiomeric programming in tripodal transition metal scaffolds
  作者：Nicholas C. Fletcher、Ciarán Martin、Heather J. Abraham

  DOI：10.1039/b703761a

  日期：——

  A new route to the isolation of the enantiopure tris-chelate complex (Δ/Λ)-fac-[Ru(L1)3]2+ (where L1 is 2,2′-bipyridine-5-carboxylic acid) is demonstrated, where the transition metal centre retains the memory of the chirality present in a simple tripodal tether used to control the metal centred geometry.

  分离对映体纯三螯合物 (Δ/Λ)-fac-[Ru(L1)3]2+ 的新途径 （其中L1是2,2'-联吡啶-5-羧酸）被证明，其中过渡金属中心保留了用于控制金属中心几何结构的简单三足系绳中存在的手性记忆。