(RS)-2-(N,N-dibenzylamino)-2-phenylethan-1-ol

• 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: (RS)-2-(N,N-dibenzylamino)-2-phenylethan-1-ol
• 英文别名: 2-(N,N-dibenzylamino)-2-phenylethan-1-ol；2-(N,N-dibenzylamino)-2-phenylethanol；2-(dibenzylamino)-2-phenylethan-1-ol；2-(Dibenzylamino)-2-phenylethanol
• 化学式: C₂₂H₂₃NO
• 分子量: 317.431
• InChiKey: AVPZXLVTKASYSW-UHFFFAOYSA-N

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：

  (RS)-2-(N,N-dibenzylamino)-2-phenylethan-1-ol 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 tert-butyl (RS,E)-4-(N,N-dibenzylamino)-4-phenylbut-2-enoate
  参考文献：
  名称：

  Parallel Kinetic Resolution of Acyclic γ-Amino-α,β-unsaturated Esters: Application to the Asymmetric Synthesis of 4-Aminopyrrolidin-2-ones

  摘要：

  Conjugate addition of a 50:50 pseudoenantiomeric mixture of lithium (R)-N-benzyl-N(alpha-methylbenzyl)amide and lithium (S)-N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide to a range of racemic acyclic gamma-amino-alpha,beta-unsaturated esters (derived from the corresponding a-amino acids) effects their efficient parallel kinetic resolution, allowing the preparation of enantiopure beta,gamma-diamino esters. The beta,gamma-dlamlno ester products of these reactions are readily converted into the corresponding substituted 4-aminopyrrolidin-2-ones via N-debenzylation and cyclization.

  DOI：

  10.1021/ol203011u
• 作为产物：
  描述：

  2-氨基-2-苯基乙酸 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 (RS)-2-(N,N-dibenzylamino)-2-phenylethan-1-ol
  参考文献：
  名称：

  Parallel Kinetic Resolution of Acyclic γ-Amino-α,β-unsaturated Esters: Application to the Asymmetric Synthesis of 4-Aminopyrrolidin-2-ones

  摘要：

  Conjugate addition of a 50:50 pseudoenantiomeric mixture of lithium (R)-N-benzyl-N(alpha-methylbenzyl)amide and lithium (S)-N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide to a range of racemic acyclic gamma-amino-alpha,beta-unsaturated esters (derived from the corresponding a-amino acids) effects their efficient parallel kinetic resolution, allowing the preparation of enantiopure beta,gamma-diamino esters. The beta,gamma-dlamlno ester products of these reactions are readily converted into the corresponding substituted 4-aminopyrrolidin-2-ones via N-debenzylation and cyclization.

  DOI：

  10.1021/ol203011u

文献信息

• [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。
• Nickel-Catalyzed Removal of Alkene Protecting Group of Phenols, Alcohols via Chain Walking Process
  作者：Chenkai Meng、Haolin Niu、Juehan Ning、Wengang Wu、Jun Yi

  DOI：10.3390/molecules25030602

  日期：——

  nickel-catalyzed removal of alkene protection group under mild condition with high functional group tolerance through chain walking process has been established. Not only phenolic ethers, but also alcoholic ethers can be tolerated with the retention of stereocenter adjacent to hydroxyl group. The new reaction brings the homoallyl group into a start of new type of protecting group.

  建立了一种在温和条件下通过链步法高效脱除烯烃保护基团的方法。不仅酚醚，而且醇醚都可以容忍与羟基相邻的立体中心的保留。新反应使高烯丙基成为新型保护基团的起点。
• 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。
• Calcium trifluoromethanesulfonate-catalysed aminolysis of epoxides
  作者：Ivica Cepanec、Mladen Litvić、Hrvoje Mikuldaš、Anamarija Bartolinčić、Vladimir Vinković

  DOI：10.1016/s0040-4020(03)00292-8

  日期：2003.3

  Aminolysis of epoxides catalysed by calcium trifluoromethanesulfonate under mild reaction conditions is described. The novel method is very efficient in the synthesis of wide variety of β-amino alcohols with high regio- and stereoselectivity.

  描述了在温和的反应条件下三氟甲磺酸钙催化的环氧化物的氨解。该新方法在合成具有高区域选择性和立体选择性的多种β-氨基醇方面非常有效。
• Regio- and stereo-selective ring opening of epoxides with amide cuprate reagents
  作者：Yoshinori Yamamoto、Naoki Asao、Masaki Meguro、Naofumi Tsukada、Hisao Nemoto、Naoki Sadayori、J. Gerald Wilson、Hiroyuki Nakamura

  DOI：10.1039/c39930001201

  日期：——

  Amide cuprate reagents attack the less hindered carbon atom of epoxides to give 1,2-amino alcohols in good yields; this procedure is applied to the synthesis of an aziridine alcohol bearing a carborane framework which is a potentially useful 10B carrier for boron neutron capture therapy.

  酰胺铜酸盐试剂可以攻击环氧化物中阻碍较少的碳原子，从而以良好的收率得到 1,2-氨基醇；这一过程被应用于合成一种带有硼烷框架的氮丙啶醇，它是硼中子俘获疗法的一种潜在有用的 10B 载体。