(S)-2-(N,N-dibenzylamino)-2-phenylethanol | 197142-90-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-(N,N-dibenzylamino)-2-phenylethanol
• 英文别名: (S)-2-(N,N-dibenzylamino)-2-phenyl-1-ethanol；2-dibenzylamino-2-phenylethanol；(2S)-2-(dibenzylamino)-2-phenylethan-1-ol；(S)-2-(dibenzylamino)-2-phenylethan-1-ol；(S)-2-dibenzylamino-2-phenylethanol；(s)-N,N-dibenzylphenylglycinol；(2S)-2-(dibenzylamino)-2-phenylethanol
• CAS: 197142-90-8
• 化学式: C₂₂H₂₃NO
• 分子量: 317.431
• InChiKey: AVPZXLVTKASYSW-JOCHJYFZSA-N

物化性质

• 沸点：
  447.8±35.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(N,N-dibenzylamino)-2-phenylethanol 在 palladium dihydroxide 草酰氯 、 氢气 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 diethyl (1S,2S)-2-[(tert-butoxycarbonyl)amino]-1-hydroxy-2-phenylethyl-phosphonate
  参考文献：
  名称：

  Stereochemistry of the addition of dialkyl phosphites to (S)-N,N-dibenzylphenylglycinal

  摘要：

  The addition of various dialkyl phosphite derivatives to (S)-N,N-dibenzylphenylglycinal 6 led to the preponderance of anti over syn diastereoisomers: from 75:25 when NEt3 or Ti(OiPr)(4) were used to 51:49 for Li or Mg salts. In the NEt3-catalysed reaction, partially racemised phosphonates were formed, while enantiomeric products were obtained after addition of lithium O,O-dimethylphosphonate to (S)-6 at -70degreesC. Because the syn-isomers were found to be resistant to O-benzoylation, Mixtures of diastereoisomers were easily separated after esterification of the anti products. Hydrogenation of the syn-phosphonates in the presence of Boc(2)O gave enantiomeric dialkyl N-Boc-2-amino-1-hydroxy-2-phenylethylphosphonates-phosphonate analogues of the docetaxel C-13 side chain. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00526-2
• 作为产物：
  描述：

  (R,S)-2-Bromo-2-phenylacetic acid (R)-pantolactone ester 在 lithium aluminium tetrahydride 、 四丁基碘化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.5h， 生成 (S)-2-(N,N-dibenzylamino)-2-phenylethanol
  参考文献：
  名称：

  Enantioselective Synthesis of β-Dibenzylamino Alcohols via a Dynamic Kinetic Resolution of α-Halo Acids

  摘要：

  DOI：

  10.1021/jo9712714

文献信息

• Chiral N-heterocyclic carbene-iridium complexes for asymmetric reduction of prochiral ketimines
  作者：Lakshay Kathuria、Ashoka G. Samuelson

  DOI：10.1016/j.poly.2020.114976

  日期：2021.2

  phenylglycine derived chiral NHC was shown to give the best Ir catalyst and it also gave the maximum ee compared to catalysts prepared from other NHCs in this series. The opposite enantiomer of the reduction product was always obtained while using the Ir complex bearing a valine based NHC. The yields were consistently high with a variety of imine substrates having different steric and electronic demands

  摘要使用一系列手性半三明治铱配合物，研究了亚胺对映体选择性还原为相应的手性仲胺。这些配合物中的手性N-杂环卡宾（NHC）配体是由易于获得的天然氨基酸合成的。廉价的苯基硅烷被用作方便的氢供体。在优化的条件下，Ir-NHC复合物可以降低酮亚胺的收率，尽管对映体过量（ee）适中。与由该系列其他NHC制备的催化剂相比，苯基甘氨酸衍生的手性NHC被证明可提供最佳的Ir催化剂，并且也可提供最大的ee。当使用带有基于缬氨酸的NHC的Ir配合物时，总是获得还原产物的相反对映异构体。
• [EN] BENZOLACTAM COMPOUNDS AS PROTEIN KINASE INHIBITORS<br/>[FR] COMPOSÉS BENZOLACTAMES UTILISÉS EN TANT QU'INHIBITEURS DE PROTÉINE KINASE
  申请人：OTSUKA PHARMA CO LTD

  公开号：WO2017068412A1

  公开（公告）日：2017-04-27

  The invention provides a compound of formula (0): or a pharmaceutically acceptable salt, N-oxide or tautomer thereof. The compounds are inhibitors of ERK 1/2 kinases and will be useful in the treatment of ERKl/2-mediated conditions. The compounds are therefore useful in therapy, in particular in the treatment of cancer.

  该发明提供了一个化合物，其化学式为(0)：或其药学上可接受的盐、N-氧化物或互变异构体。这些化合物是ERK 1/2激酶的抑制剂，并将在治疗ERKl/2介导的疾病中发挥作用。因此，这些化合物在治疗中特别是在癌症治疗中是有用的。
• Stereoselective and Regioselective Intramolecular Friedel–Crafts Reaction of Aziridinium Ions for Synthesis of 4-Substituted Tetrahydroisoquinolines
  作者：Hyun-Soon Chong、Yunwei Chen

  DOI：10.1021/ol4013537

  日期：2013.12.6

  Optically active 4-substituted tetrahydroisoquinolines were synthesized via intramolecular Friedel–Crafts (FC) reactions of aziridinium ions in a highly regio- and stereoselective manner. Control experiments suggest the formation and ring-opening of aziridinium ions as the key intermediates in the Lewis acid catalyzed FC reactions.

  通过氮丙啶鎓离子的分子内弗里德尔-克来福特 (FC) 反应以高度区域和立体选择性方式合成了光学活性 4-取代四氢异喹啉。对照实验表明氮丙啶鎓离子的形成和开环是路易斯酸催化 FC 反应中的关键中间体。
• Synthesis of Enantiopure <i>syn</i>-β-Amino Alcohols. A Simple Case of Chelation-Controlled Additions of Diethylzinc to α-(Dibenzylamino) Aldehydes
  作者：José M. Andrés、Roberto Barrio、María A. Martínez、Rafael Pedrosa、Alfonso Pérez-Encabo

  DOI：10.1021/jo960017t

  日期：1996.1.1

  Enantiomerically pure syn-2-amino alcohols 6 are prepared by addition of diethylzinc to chiral alpha-(dibenzylamino) aldehydes 4. The addition is highly stereoselective, leading to syn-2-(dibenzylamino) alcohols 5 with excellent diastereomeric excesses (76-98%). Debenzylation of 5 by hydrogenolysis on Pearlman's catalyst yields quantitatively the amino alcohols 6.

  对映体纯的顺式-2-氨基醇6是通过将二乙基锌加到手性α-（二苄基氨基）醛4上而制备的。该加成物具有高度的立体选择性，从而制得具有出色的非对映异构体过量的顺式2-（二苄基氨基）醇5（76-98 ％）。通过在Pearlman催化剂上进行氢解将5脱苄基化，可定量得到氨基醇6。
• Stereoselective formation and rearrangement of morpholinium ylides derived from copper carbenoids
  作者：Kevin W. Glaeske、B.N. Naidu、F.G. West

  DOI：10.1016/s0957-4166(03)00095-8

  日期：2003.4

  Amino diazoacetoacetates 4a–e and 7a,b were prepared from readily available amino alcohols and subjected to copper-catalyzed carbene-transfer reaction. Substrates 4c–e furnished the morpholin-2-ones 5c–e in good yield via the corresponding cyclic ammonium ylides, albeit with poor diastereoselectivity. Substrates 4a,b failed to provide the corresponding morpholinones, perhaps as a result of steric congestion

  氨基重氮乙酰乙酸酯4a – e和7a，b由容易获得的氨基醇制备，并进行铜催化的卡宾转移反应。尽管非对映选择性差，但底物4c – e通过相应的环状铵盐以高收率提供了吗啉-2-酮5c – e。底物4a，b可能不能提供相应的吗啉酮，这可能是由于空间拥挤的结果。环状底物7a，b经历转化为双环吗啉酮8和9收率高，非对映选择性中等。通过控制中间双环烷基化物的瞬时立体异构的铵中心，可以合理化该结果。