4-(2-hydroxyethyl)-8a-methoxy-7-methyl-3,4-dihydro-2H-1,4-benzoxazin-6(8aH)-on | 133712-69-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 4-(2-hydroxyethyl)-8a-methoxy-7-methyl-3,4-dihydro-2H-1,4-benzoxazin-6(8aH)-on
• 英文别名: 4-(2-Hydroxyethyl)-8a-methoxy-7-methyl-2,3-dihydro-1,4-benzoxazin-6-one
• CAS: 133712-69-3
• 化学式: C₁₂H₁₇NO₄
• 分子量: 239.271
• InChiKey: PZBHLUARRCDYMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  重氮乙烷 、 4-(2-hydroxyethyl)-8a-methoxy-7-methyl-3,4-dihydro-2H-1,4-benzoxazin-6(8aH)-on 以 氯仿 为溶剂， 反应 3.0h， 以90%的产率得到(3aS,9aR,9bR)-6-(2-Hydroxy-ethyl)-9a-methoxy-1,3a-dimethyl-1,3a,7,8,9a,9b-hexahydro-6H-9-oxa-2,3,6-triaza-cyclopenta[a]naphthalen-4-one
  参考文献：
  名称：

  Zur Umsetzung von 3,4-Dihydro-8a-methoxy-2H-1,4-benzoxazin-6(8aH)-onen mit Diazoalkanen, 1. Mitt.

  摘要：

  3,4-Dihydro-8a-methoxy-2H-1,4-benzoxazin-6(8a')-ones - quinol derivatives of 2-hydroxyethylamino-1, 4-benzoquinones - react with diazoalkanes to yield 2,3,9a,9b-Tetrahydro-9H-pyrazolo[3,4-h]-1, 4-benzoxazin-6(6 aH)-ones (3). Their structures were established on basis of NMR-techniques including two-dimensional experiments. The orientation phenomena of the reaction is discussed.

  DOI：

  10.1007/bf00815165
• 作为产物：
  描述：

  2-bis(2-hydroxy-ethyl)amino-5-methyl-1,4-benzoquinol 、 碘甲烷 在 silver(l) oxide 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以73%的产率得到4-(2-hydroxyethyl)-8a-methoxy-7-methyl-3,4-dihydro-2H-1,4-benzoxazin-6(8aH)-on
  参考文献：
  名称：

  Zur Umsetzung von 3,4-Dihydro-8a-methoxy-2H-1,4-benzoxazin-6(8aH)-onen mit Diazoalkanen, 1. Mitt.

  摘要：

  3,4-Dihydro-8a-methoxy-2H-1,4-benzoxazin-6(8a')-ones - quinol derivatives of 2-hydroxyethylamino-1, 4-benzoquinones - react with diazoalkanes to yield 2,3,9a,9b-Tetrahydro-9H-pyrazolo[3,4-h]-1, 4-benzoxazin-6(6 aH)-ones (3). Their structures were established on basis of NMR-techniques including two-dimensional experiments. The orientation phenomena of the reaction is discussed.

  DOI：

  10.1007/bf00815165

文献信息

• Reactions of 2H-3,4-dihydro-1,4-benzoxazin-6(8aH)-ones with 2,4,6-trimethylbenzonitrile oxide, III
  作者：M. Schubert-Zsilavecz、D. Gusterhuber、W. Likussar、G. F�rber

  DOI：10.1007/bf01277634

  日期：1994.6

  Regio-, stereo- and siteselectivity of the cycloadditions of trimethylbenzonitrile oxide with 2H-3,4-Dihydro-1,4-benzoxazin-6(8aH)-ones have been investigated. The structures of the obtained products were elucidated by means of homonuclear NOE difference spectroscopy and HMQC and HMBC spectra. The structure of 6-Benzyl-9a-methoxy-3-mesityl-9b-methyl-7,8,9a,9b-tetrahydro-3aH-1,2-oxazolo-[4,5-h]1,4-benzoxazin-4(6H)-on 5 was elucidated from a single crystal X-ray structure analysis at ambient temperature: C27H30N2O4, M=446.55 g/mol, monoclinic, P2(1)/c, a = 10.372 (34) angstrom, b = 11.908 (21) angstrom, c = 20.040 (34) angstrom, beta = 97.16 (17)-degrees, V = 2455.8 (1.9) angstrom3, Z = 4, d(c) = 1.208 g/cm3, mu = 0.08 mm-1, R = 0.0546.
• SCHUBERT-ZSILAVECZ, MANFRED, MONATSH. CHEM., 122,(1991) N-2, C. 51-57
  作者：SCHUBERT-ZSILAVECZ, MANFRED

  DOI：——

  日期：——
• Schubert-Zsilavecz M., Gusterhuber D., Likussar W., Faerber G., Monatsh. Chem, 125 (1994) N 6-7, S 735-742
  作者：Schubert-Zsilavecz M., Gusterhuber D., Likussar W., Faerber G.

  DOI：——

  日期：——
• Zur Umsetzung von 3,4-Dihydro-8a-methoxy-2H-1,4-benzoxazin-6(8aH)-onen mit Diazoalkanen, 1. Mitt.
  作者：Manfred Schubert-Zsilavecz

  DOI：10.1007/bf00815165

  日期：——

  3,4-Dihydro-8a-methoxy-2H-1,4-benzoxazin-6(8a')-ones - quinol derivatives of 2-hydroxyethylamino-1, 4-benzoquinones - react with diazoalkanes to yield 2,3,9a,9b-Tetrahydro-9H-pyrazolo[3,4-h]-1, 4-benzoxazin-6(6 aH)-ones (3). Their structures were established on basis of NMR-techniques including two-dimensional experiments. The orientation phenomena of the reaction is discussed.