L-phenylglycine allyl ester | 113371-32-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: L-phenylglycine allyl ester
• 英文别名: prop-2-enyl (2S)-2-amino-2-phenylacetate
• CAS: 113371-32-7
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: PJUXPSLKVXHJGW-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-phenylglycine allyl ester 在 WSCD*HCl 、 1-羟基苯并三唑 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 prop-2-enyl (2S)-2-[[(2S)-2-aminopropanoyl]amino]-2-phenylacetate
  参考文献：
  名称：

  Parallel synthesis of DAPT derivatives and their γ-secretase-inhibitory activity

  摘要：

  Parallel synthesis of the C-terminal-modified DAPT (1) derivatives was accomplished utilizing our novel resin 7. Condensation reaction of the N-acylamino acid 10 with the amines 11a-o proceeded smoothly to give the corresponding amides 6a-o without any epimerization. Among the analogues, the benzophenonemethyl amide derivative 6o showed 30 times more potent activity than the original DAPT (1). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.067
• 作为产物：
  描述：

  L-苯甘氨酸 、 烯丙醇 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 L-phenylglycine allyl ester
  参考文献：
  名称：

  通过钯催化的分子内重排合成α-烯丙基-α-氨基酸

  摘要：

  通过催化量的Pd（O）配合物进行重排，氨基酸亚胺的烯丙基酯可提供高收率的α-烷基化-α-氨基酸。

  DOI：

  10.1016/s0040-4039(00)80658-9

文献信息

• Synthesis of α-allyl-α-amino acids by means of a palladium catalyzed intramolecular rearrangement
  作者：Anne van der Werf、Richard M. Kellogg

  DOI：10.1016/s0040-4039(00)80658-9

  日期：1988.1

  Allylic esters of imines of amino acids provide α-alkylated-α-amino acids in good yields, on rearrangement by catalytic quantities of Pd(O) complexes.

  通过催化量的Pd（O）配合物进行重排，氨基酸亚胺的烯丙基酯可提供高收率的α-烷基化-α-氨基酸。
• Basic esters of fatty alcohols and their use as anti-inflammatory or immunomodulatory agents
  申请人：Shinitzky Meir

  公开号：US20060173053A1

  公开（公告）日：2006-08-03

  Basic esters of fatty alcohols of the general formula: R1-O—CO-A or pharmaceutically acceptable salts thereof, wherein R1 is C 12 -C 24 alkyl or C 10 -C 24 alkenyl, and A is a residue containing at least one acyclic or cyclic amino group and/or at least one heteroaromatic ring containing a tertiary or quaternary nitrogen atom, are anti-inflammatory and immunomodulatory agents, useful in the treatment of immunologically-mediated inflammation, as adjuvants for antigens involved in both cellular and humoral responses.

  一般式为R1-O-CO-A的脂肪醇基本酯或其药学上可接受的盐，其中R1为C12-C24烷基或C10-C24烯基，A为含有至少一个无环或环状氨基团和/或至少一个含有三级或四级氮原子的杂环芳香环的残基，具有抗炎和免疫调节作用，可用于治疗免疫介导的炎症，并作为细胞和体液反应中涉及的抗原的佐剂。
• BASIC ESTERS OF FATTY ALCOHOLS AND THEIR USE AS ANTI-INFLAMMATORY OR IMMUNOMODULATORY AGENTS
  申请人：YEDA RESEARCH AND DEVELOPMENT CO. LTD.

  公开号：EP1551495A2

  公开（公告）日：2005-07-13
• US8987263B2
  申请人：——

  公开号：US8987263B2

  公开（公告）日：2015-03-24
• [EN] BASIC ESTERS OF FATTY ALCOHOLS AND THEIR USE AS ANTI-INFLAMMATORY OR IMMUNOMODULATORY AGENTS<br/>[FR] ESTERS DE BASE D'ALCOOLS GRAS ET LEUR UTILISATION COMME AGENTS ANTI-INFLAMMATOIRES OU IMMUNOMODULATEURS
  申请人：YEDA RES & DEV

  公开号：WO2004032824A2

  公开（公告）日：2004-04-22

  Basic esters of fatty alcohols of the general formula: R1-O-CO-A or pharmaceutically acceptable salSt thereof, wherein R1 is C12-C24 alkyl or C10-C24 alkenyl, and A is a residue containing at least one acyclic or cyclic amino group and/or at least one heteroaromatic ring containing a tertiary or quaternary nitrogen atom, are anti-inflammatory and immunomodulatory agents, useful in the treatment of immunologically-mediated inflammation, and as adjuvants for antigens involved in both cellular and humoral responses.