ethyl 3-amino-2-hydroxy-2-phenylpropanoate | 99986-48-8

• 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: ethyl 3-amino-2-hydroxy-2-phenylpropanoate
• 英文别名: 3-Amino-2-hydroxy-2-phenyl-propionsaeure-aethylester
• CAS: 99986-48-8
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: QRDNNIKOXHAIFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-2-hydroxy-2-phenylpropanoate 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 异丙胺 、 三乙胺 作用下， 以 二氯甲烷 、 异丙醇 、 乙腈 为溶剂， 反应 64.0h， 生成 ethyl 2-((1,2,3,5,6.7-hexahydro-s-indacen-4-yl)amino)-5-phenyl-4,5-dihydrooxazole-5-carboxylate
  参考文献：
  名称：

  [EN] DIHYDROOXAZOLE AND THIOUREA OR UREA DERIVATIVES MODULATING THE NLRP3 INFLAMMASOME PATHWAY
  [FR] DÉRIVÉS DE DIHYDROOXAZOLE ET DE THIOURÉE MODULANT LA VOIE INFLAMMATOIRE NLRP3

  摘要：

  公开号：

  WO2021255279A8
• 作为产物：
  描述：

  (ethoxycarbonyl)(cyano)(phenyl)methyl dimethyl phosphate 在 镍 氢气 作用下， 以 乙醇 为溶剂， 生成 ethyl 3-amino-2-hydroxy-2-phenylpropanoate
  参考文献：
  名称：

  Cyanide Ion Promoted Addition of Acyl Phosphonates to Ethyl Cyanoformate:  Synthesis of Tertiary Carbinols via Tandem Carbon−Carbon Bond Formations

  摘要：

  [GRAPHICS]New cyanation/phosphonate -phosphate rearrangement/Cacylation reactions of cyartophosphate anion with cyanoformate esters are described. Phase-transfer cocatalysts facilitate cyanide-catalyzed reactions between acyl phosphonates and cyanoformates to afford protected tertiary carbinol products in good to excellent yields (74-95%). Ethyl cyanoformate is used as a cyanide source and electrophile. The scope of the reaction was investigated by using a number of benzoyl and acyl phosphonates along with ethyl cyanoformate. Representative chemoselective reduction of the product 5a afforded ethyl 3-amino-2- iydroxy-2-phenylpropanoate (13) in good yield.

  DOI：

  10.1021/jo0710073

文献信息

• Testa,E. et al., Justus Liebigs Annalen der Chemie, 1961, vol. 639, p. 166 - 180
  作者：Testa,E. et al.

  DOI：——

  日期：——
• Mercapto-acylamino acids
  申请人：SCHERING CORPORATION

  公开号：EP0393441B1

  公开（公告）日：1993-05-26
• US5219886A
  申请人：——

  公开号：US5219886A

  公开（公告）日：1993-06-15
• [EN] D I H YD ROOXAZO LE AND THIOUREA DERIVATIVES MODULATING THE NLRP3 INFLAMMASOME PATHWAY<br/>[FR] DÉRIVÉS DE DIHYDROOXAZOLE ET DE THIOURÉE MODULANT LA VOIE INFLAMMATOIRE NLRP3
  申请人：[en]AC IMMUNE SA

  公开号：WO2021255279A1

  公开（公告）日：2021-12-23

  The invention relates to novel compounds of formulae (I') and (II') for the treatment, alleviation or prevention of diseases, disorders and abnormalities which are responsive to the modulation or inhibition of the activation of a component of the NLRP3 inflammasome pathway. In particular, the component of the inflammasome pathway is a NOD- like receptor (NLR) family, pyrin domain-containing protein 3 (NLRP3) inflammasome. More particularly, the compounds of the present invention have the capability to modulate the NLRP3 inflammasome pathway. Further, the compounds of the present invention are suitable for the treatment, alleviation or prevention of diseases, disorders and abnormalities which are responsive to the modulation, in particular decrease, of IL-1 beta and/or IL-18 levels.
• Cyanide Ion Promoted Addition of Acyl Phosphonates to Ethyl Cyanoformate:  Synthesis of Tertiary Carbinols via Tandem Carbon−Carbon Bond Formations
  作者：Ayhan S. Demir、Barbaros Reis、Ömer Reis、Serkan Eymür、Mehmet Göllü、Servet Tural、Gülüzar Saglam

  DOI：10.1021/jo0710073

  日期：2007.9.1

  [GRAPHICS]New cyanation/phosphonate -phosphate rearrangement/Cacylation reactions of cyartophosphate anion with cyanoformate esters are described. Phase-transfer cocatalysts facilitate cyanide-catalyzed reactions between acyl phosphonates and cyanoformates to afford protected tertiary carbinol products in good to excellent yields (74-95%). Ethyl cyanoformate is used as a cyanide source and electrophile. The scope of the reaction was investigated by using a number of benzoyl and acyl phosphonates along with ethyl cyanoformate. Representative chemoselective reduction of the product 5a afforded ethyl 3-amino-2- iydroxy-2-phenylpropanoate (13) in good yield.