(-)-(2S)-2-benzyloxycarbonylamino-1,3-diphenyl-propane-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (-)-(2S)-2-benzyloxycarbonylamino-1,3-diphenyl-propane-1-one
• 英文别名: (S)-benzyl 1-oxo-1,3-diphenylpropan-2-ylcarbamate；Cbz-L-Phe-benzene；benzyl N-[(2S)-1-oxo-1,3-diphenylpropan-2-yl]carbamate
• 化学式: C₂₃H₂₁NO₃
• 分子量: 359.425
• InChiKey: QYPGLIYNEKBOLW-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酸 在 tris(dibenzylideneacetone)dipalladium (0) Cu(I) thiophenecarboxylate 、 N,N'-二环己基碳二亚胺 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 (-)-(2S)-2-benzyloxycarbonylamino-1,3-diphenyl-propane-1-one
  参考文献：
  名称：

  肽基硫醇酯-硼酸交叉偶联法在常温下合成高对映纯度N保护的肽基酮

  摘要：

  在化学计量的 Cu(I) 噻吩-2-羧酸盐和催化作用下，衍生自 N-保护的单肽、二肽和三肽的 α-氨基酸硫羟酸酯与芳基、富含 π 电子的杂芳基或烯基硼酸偶联Pd(2)(dba)(3)/亚磷酸三乙酯生成相应的 N 保护肽基酮，产率和对映体纯度都非常好。亚磷酸三乙酯通过减轻不希望的钯催化脱羰-β-消除α-氨基硫羟酸酯，作为支持配体发挥关键作用。肽基酮的合成在室温下非碱性条件下进行，并表现出对功能的高度耐受性。

  DOI：

  10.1021/ja0658719

文献信息

• Synthesis of High Enantiopurity N-Protected α-Amino Ketones by Thiol Ester−Organostannane Cross-Coupling Using pH-Neutral Conditions
  作者：Hao Li、Hao Yang、Lanny S. Liebeskind

  DOI：10.1021/ol8018456

  日期：2008.10.2

  efficient synthesis of high enantiopurity N-protected alpha-amino ketones is described. Complementing other studies using boronic acids and thiol esters, this Cu(I) diphenylphosphinate (CuDPP)-mediated, palladium-catalyzed coupling of alpha-amino thiol esters with aryl, heteroaryl, allyl, and alkenyl organostannanes gives N-protected alpha-amino ketones in high yields with high enantiopurity (in almost

  描述了高对映纯度 N 保护的 α-氨基酮的有效合成。作为使用硼酸和硫羟酸酯的其他研究的补充，这种二苯基次膦酸铜 (CuDPP) 介导的钯催化的 α-氨基硫羟酸酯与芳基、杂芳基、烯丙基和烯基有机锡烷的偶联得到 N-保护的 α-氨基酮在温和和 pH 中性的反应条件下以高产率和高对映体纯度（几乎在所有情况下）。与相关的硼酸系统相比，缺乏 pi 的杂芳基锡烷的生存能力是该反应的一个优势。
• A novel ketone synthesis by a palladium-catalyzed reaction of thiol esters and organozinc reagents
  作者：Hidetoshi Tokuyama、Satoshi Yokoshima、Tohru Yamashita、Tohru Fukuyama

  DOI：10.1016/s0040-4039(98)00456-0

  日期：1998.5

  A variety of ketones have been prepared by a palladium-catalyzed reaction of ethanethiol esters with organozinc reagents. Various functional groups, including esters, ketones, aromatic halides and aldehydes, tolerate the reaction conditions. The reaction can also be applied to the synthesis of α-amino ketones using the corresponding L-α-amino thiol esters without racemization.

  通过乙硫醇酯与有机锌试剂的钯催化反应已制备了多种酮。包括酯，酮，芳族卤化物和醛在内的各种官能团可耐受反应条件。该反应也可用于使用相应的L-α-氨基硫醇酯而无需外消旋作用的合成α-氨基酮。
• CamTHP*OH:  A Camphor-Derived δ-Lactol Auxiliary for the Effective Desymmetrization of Attached Glycinamide Residues. Asymmetric Synthesis of α-Amino Carbonyl Compounds
  作者：Darren J. Dixon、Richard A. J. Horan、Nathaniel J. T. Monck

  DOI：10.1021/ol048569i

  日期：2004.11.1

  Stereoselective allylation of camphor and subsequent terminal hydroformylation affords a new delta-lactol auxiliary (camTHP*OH) on multigram scale. Stereoselective condensation with glycine dimethylamide and Cbz protection affords a camTHP*-desymmetrized glycinamide building block which undergoes efficient and highly diastereoselective metal enolate alkylation reactions. Acid-mediated deprotection affords the N-Cbz-protected a-amino amide products which may be converted directly to alpha-amino ketones on treatment with Grignard or organolithium reagents without loss of stereochemical integrity.
• NOVEL COMPOUNDS
  申请人：Heiser Ulrich

  公开号：US20100273835A1

  公开（公告）日：2010-10-28

  The invention provides compounds of general formula (I) or a pharmaceutically acceptable salt, polymorph or solvate thereof, including all tautomers and stereoisomers thereof, wherein K, W, X; Y and Z are described throughout the description and claims. The compounds of the present invention are useful as inhibitors of prolyl endopeptidase (PEP, EC 3.4.21.26) and/or IL-6.
• [EN] NOVEL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS
  申请人：PROBIODRUG AG

  公开号：WO2009007415A2

  公开（公告）日：2009-01-15

  The invention provides compounds of general formula (I) or a pharmaceutically acceptable salt, polymorph or solvate thereof, including all tautomers and stereoisomers thereof, wherein K, W, X; Y and Z are described throughout the description and claims. The compounds of the present invention are useful as inhibitors of prolyl endopeptidase (PEP, EC 3.4.21.26) and/or IL-6.