(R)-3-{2-[(R)-1-(2-Hydroxy-ethoxy)-ethyl]-4-oxo-4H-quinazolin-3-ylamino}-3-phenyl-propionic acid methyl ester | 445397-20-6

• 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: (R)-3-{2-[(R)-1-(2-Hydroxy-ethoxy)-ethyl]-4-oxo-4H-quinazolin-3-ylamino}-3-phenyl-propionic acid methyl ester
• 英文别名: methyl (3R)-3-[[2-[(1R)-1-(2-hydroxyethoxy)ethyl]-4-oxoquinazolin-3-yl]amino]-3-phenylpropanoate
• CAS: 445397-20-6
• 化学式: C₂₂H₂₅N₃O₅
• 分子量: 411.458
• InChiKey: UPPYTZORHKHPQU-DNVCBOLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-3-{2-[(R)-1-(2-Hydroxy-ethoxy)-ethyl]-4-oxo-4H-quinazolin-3-ylamino}-3-phenyl-propionic acid methyl ester 在 N,N-二甲基乙醇胺 、 samarium diiodide 作用下， 以40%的产率得到(R)-3-氨基-3-苯基 丙酸甲酯
  参考文献：
  名称：

  Completely diastereoselective aziridination of α,β-unsaturated acids via intramolecular reaction of 3-acetoxyaminoquinazolin-4(3H)-ones

  摘要：

  (R)-3-Amino-2-[1-(2-hydroxyethoxy)ethyl]quinazolin-4(3H)-one 10 was prepared in 62% yield without the need for chromatography and O-cinnamoylated reaction with lead tetra-acetate gave aziridine 12 as a single diastereoisomer in quantitative yield which was converted into the beta-amino acid ester 15 corresponding to overall enantioselective addition of ammonia to the double bond of cinnamic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00136-3
• 作为产物：
  描述：

  (R)-2-(2-benzyloxyethoxy)propionic acid 在 吡啶 、 lead(IV) acetate 、 samarium diiodide 、 sodium methylate 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 叔丁醇 为溶剂， 生成 (R)-3-{2-[(R)-1-(2-Hydroxy-ethoxy)-ethyl]-4-oxo-4H-quinazolin-3-ylamino}-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  Completely diastereoselective aziridination of α,β-unsaturated acids via intramolecular reaction of 3-acetoxyaminoquinazolin-4(3H)-ones

  摘要：

  (R)-3-Amino-2-[1-(2-hydroxyethoxy)ethyl]quinazolin-4(3H)-one 10 was prepared in 62% yield without the need for chromatography and O-cinnamoylated reaction with lead tetra-acetate gave aziridine 12 as a single diastereoisomer in quantitative yield which was converted into the beta-amino acid ester 15 corresponding to overall enantioselective addition of ammonia to the double bond of cinnamic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00136-3

文献信息

• Completely diastereoselective aziridination of α,β-unsaturated acids via intramolecular reaction of 3-acetoxyaminoquinazolin-4(3H)-ones
  作者：Robert S Atkinson、Richard D Draycott、David J Hirst、Martin J Parratt、Tony M Raynham

  DOI：10.1016/s0040-4039(02)00136-3

  日期：2002.3

  (R)-3-Amino-2-[1-(2-hydroxyethoxy)ethyl]quinazolin-4(3H)-one 10 was prepared in 62% yield without the need for chromatography and O-cinnamoylated reaction with lead tetra-acetate gave aziridine 12 as a single diastereoisomer in quantitative yield which was converted into the beta-amino acid ester 15 corresponding to overall enantioselective addition of ammonia to the double bond of cinnamic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.