N8,6-di(4-nitrophenyl)-(3R)-ethyl-(7R)-methyl-5-oxo-2,3,6,7-tetrahydrooxazolo<3,2,c>pyrimidine-8-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N8,6-di(4-nitrophenyl)-(3R)-ethyl-(7R)-methyl-5-oxo-2,3,6,7-tetrahydrooxazolo<3,2,c>pyrimidine-8-carboxamide
• 英文别名: (3R,7R)-N,6-Bis(4-nitrophenyl)-3-ethyl-7-methyl-5-oxo-2,3,6,7-tetrahydro-5H-[1,3]oxazolo[3,2-c]pyrimidine-8-carboxamide；(3R,7R)-3-ethyl-7-methyl-N,6-bis(4-nitrophenyl)-5-oxo-3,7-dihydro-2H-[1,3]oxazolo[3,2-c]pyrimidine-8-carboxamide
• 化学式: C₂₂H₂₁N₅O₇
• 分子量: 467.438
• InChiKey: TZLMCSRXYUNBFN-UKRRQHHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  154
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (E)-N-[(2R)-1-Hydroxybutan-2-yl]but-2-enamide 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 N8,6-di(4-nitrophenyl)-(3R)-ethyl-(7R)-methyl-5-oxo-2,3,6,7-tetrahydrooxazolo<3,2,c>pyrimidine-8-carboxamide
  参考文献：
  名称：

  Highly diastereoselective hetero-Diels–Alder reactions of alkenyldihydrooxazoles as an approach to novel pyrimidine derivatives

  摘要：

  手性 2-烯基二氢恶唑与两个等量的芳基和芳基磺酰基异氰酸酯发生反应，生成手性非外消旋二氢嘧啶酮衍生物，产量高且完全非对映控制。

  DOI：

  10.1039/a705571d

文献信息

• Asymmetric hetero-Diels–Alder reactions of alkenyldihydrooxazoles. Synthesis of oxazolo[3,2-c]pyrimidines and related compounds
  作者：Mark C. Elliott、Elbertus Kruiswijk

  DOI：10.1039/a905700e

  日期：——

  Alkenyldihydrooxazoles undergo a highly diastereoselective formal aza-Diels–Alder reaction with aryl and arenesulfonyl isocyanates to give oxazolo[3,2-c]pyrimidines. Depending on the substitution pattern of the alkenyldihydrooxazole, these compounds may then undergo addition of a second equivalent of the isocyanate to give either tetrahydrooxazolo[3,2-c]pyrimidine-8-carboxamides or octahydroazeto[2

  烯基二氢恶唑与芳基和芳烃磺酰基异氰酸酯进行高度非对映选择性的正式aza-Diels-Alder反应，生成oxazolo [3,2- c ]嘧啶。然后，根据烯基二氢恶唑的取代方式，可以将这些化合物加入第二当量的异氰酸酯，以得到四氢恶唑并[ 3,2 - c ]嘧啶-8-羧酰胺或八氢氮杂并[2,3- d ]恶唑[3]。 ，2- c ]嘧啶。第二种添加对空间和电子因素敏感，在某些情况下可以防止。
• ——
  作者：Mark C. Elliott、David E. Hibbs、David S. Hughes、Michael B. Hursthouse、Elbertus Kruiswijk、K. M. Abdul Malik

  DOI：10.1023/a:1021791832534

  日期：——

  Three novel dihydropyrimidine compounds N8,6-di(4-nitrophenyl)-(3R)-ethyl-(7R)-methyl-5-oxo-2,3,6,7-tetrahydrooxazolo[3,2,c] pyrimidine-8-carboxamide (2), N8,6-di((4-methylphenyl)sulfonyl)-(3R)-ethyl-5-oxo-(7R)-phenyl-2,3,6,7-tetrahydrooxazolo [3,2,c]pyrimidine-8-carboxamide (3) and N8,6-di ((4-methylphenyl)sulfonyl)-(3R)-ethyl-(7R)-methyl-5-oxo-2,3,6,7- tetrahydrooxazolo[3.2,c] pyrimidine-8-carboxamide (4) have been prepared (from 2-amino-1-butanol of 64.4% e.e.) and structurally characterized by X-ray crystallography. All three compounds contain stereogenic centers, but the crystal of (2) chosen was found to be racemic whilst those of (3) and (4) were found to be homochiral. Compound (2) crystallizes in the monoclinic space group P2(1)/c, with a = 17.958(4), b = 12.431(2), c = 9.653(2) Angstrom, beta = 96.20(3)degrees, U = 2142.3(7) Angstrom(3), Z = 4, and D-c = 1.449 g cm(-3). Compounds (3) and (4) both crystallize in the monoclinic space group P2(1), with a = 9.349(2), b = 5.824(5), c = 26.513(8) Angstrom, beta = 99.43(2)degrees, U = 1424.1(13) Angstrom(3), Z = 2 and D-c = 1.389 g cm(-3) for (3), and a = 5.9526(9), b = 16.3521(10), c = 13.2263(11) Angstrom, beta = 92.81(12)degrees, U = 1285.9(2) Angstrom(3), Z = 2 and D-c = 1.378 g cm(-3) for (4).
• Highly diastereoselective hetero-Diels–Alder reactions of alkenyldihydrooxazoles as an approach to novel pyrimidine derivatives
  作者：Mark C. Elliott、Elbertus Kruiswijk

  DOI：10.1039/a705571d

  日期：——

  Chiral 2-alkenyldihydrooxazoles react with two equivalents of aryl and arylsulfonyl isocyanates to give chiral nonracemic dihydropyrimidone derivatives in high yield and with complete diastereocontrol.

  手性 2-烯基二氢恶唑与两个等量的芳基和芳基磺酰基异氰酸酯发生反应，生成手性非外消旋二氢嘧啶酮衍生物，产量高且完全非对映控制。