(R)-3-amino-2-[1-(2-hydroxyethoxy)ethyl]quinazolin-4-(3H)-one | 445397-17-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (R)-3-amino-2-[1-(2-hydroxyethoxy)ethyl]quinazolin-4-(3H)-one
• 英文别名: 2-[(1R)-1-(3-amino-4-oxoquinazolin-2-yl)ethoxy]ethyl (E)-3-phenylprop-2-enoate
• CAS: 445397-17-1
• 化学式: C₂₁H₂₁N₃O₄
• 分子量: 379.415
• InChiKey: PUBRWPAACLQLPN-AYJWMTRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-3-amino-2-[1-(2-hydroxyethoxy)ethyl]quinazolin-4-(3H)-one 在 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
• 作为产物：
  描述：

  (R)-2-(2-benzyloxyethoxy)propionic acid 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-3-amino-2-[1-(2-hydroxyethoxy)ethyl]quinazolin-4-(3H)-one
  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.