(4R)-4-ethyl-2-(1-propenyl)-4,5-dihydro-1,3-oxazole | 201005-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: (4R)-4-ethyl-2-(1-propenyl)-4,5-dihydro-1,3-oxazole
• 英文别名: (4R)-ethyl-2-(1-propenyl)-4,5-dihydro-1,3-oxazole；(4R)-4-Ethyl-2-propenyl-4,5-dihydro-1,3-oxazole；(4R)-ethyl-2-(1-propenyl)-4,5-dihydrooxazole；(4R)-4-ethyl-2-[(E)-prop-1-enyl]-4,5-dihydro-1,3-oxazole
• CAS: 201005-60-9
• 化学式: C₈H₁₃NO
• 分子量: 139.197
• InChiKey: DYQODPRSVGBYOS-OHCKJTPYSA-N

物化性质

• 沸点：
  157.6±9.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  异氰酸对硝基苯 、 (4R)-4-ethyl-2-(1-propenyl)-4,5-dihydro-1,3-oxazole 反应 21.0h， 以82%的产率得到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
• 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， 以74%的产率得到(4R)-4-ethyl-2-(1-propenyl)-4,5-dihydro-1,3-oxazole
  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。
• Asymmetric Hetero-Diels-Alder Reactions with Heterocumulenes
  作者：Mark C. Elliott、Alexandra E. Monk、Elbertus Kruiswijk、David E. Hibbs、Robert L. Jenkins、David V. Jones

  DOI：10.1055/s-1999-2853

  日期：1999.9

  Chiral 2-alkenyloxazolines and 2-alkenylthiazolines react with isocyanates and ketenes to give formal hetero-Diels-Alder adducts with complete diastereocontrol. In each case an electron-rich double bond in the adduct is prone to a second addition of the heterocumulene. In the case of the oxazoline adducts the second addition is faster than the first, while with thiazolines the second addition is slower

  手性 2-链烯基恶唑啉和 2-链烯基噻唑啉与异氰酸酯和乙烯酮反应，生成具有完全非对映控制的正式杂狄尔斯-阿尔德加合物。在每种情况下，加合物中的富电子双键易于再次加成杂枯草烯。在恶唑啉加合物的情况下，第二次加成比第一次快，而对于噻唑啉，第二次加成更慢，因此可以加入不同的杂枯草烯。
• Asymmetric hetero-Diels-Alder reactions. Mechanism of the reaction of alkenyloxazolines with isocyanates
  作者：Mark C. Elliott、Elbertus Kruiswijk、David J. Willock

  DOI：10.1016/s0040-4039(98)01949-2

  日期：1998.11

  Diastereomerically pure oxazolo[3,2-c]pyrimidines can be readily prepared by the reaction of alkenyloxazolines with isocyanates. These compounds undergo epimerisation upon prolonged heating. The mechanism of this transformation has been investigated experimentally and computationally.

  通过链烯基恶唑啉与异氰酸酯的反应可以容易地制备非对映体纯的恶唑并[3，2- c ]嘧啶。这些化合物在长时间加热下会发生差向异构。已经通过实验和计算研究了这种转化的机理。
• Asymmetric hetero-Diels–Alder reactions. Reactions of oxazolo[3,2- c ]pyrimidines
  作者：Mark C Elliott、Elbertus Kruiswijk、David J Willock

  DOI：10.1016/s0040-4020(01)01032-8

  日期：2001.12

  Diastereomerically pure oxazolo[3,2-c]pyrimidines can be readily prepared by the reaction of alkenyloxazolines with isocyanates. The mechanism of this transformation has been investigated computationally. These compounds undergo epimerisation upon prolonged heating, a reaction which is consistent with the proposed stepwise mechanism. Hydrolysis reactions of these compounds have been investigated. (C) 2001 Elsevier Science Ltd. All rights reserved.
• ——
  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).