(4S,5R)-3-(furan-2-carbonyl)-5-methyl-N-(8-oxo-5,6,7,8-tetrahydronaphthalen-1-yl)oxazolidine-4-carboxamide | 1415588-51-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (4S,5R)-3-(furan-2-carbonyl)-5-methyl-N-(8-oxo-5,6,7,8-tetrahydronaphthalen-1-yl)oxazolidine-4-carboxamide
• 英文别名: (4S,5R)-3-(furan-2-carbonyl)-5-methyl-N-(8-oxo-6,7-dihydro-5H-naphthalen-1-yl)-1,3-oxazolidine-4-carboxamide
• CAS: 1415588-51-0
• 化学式: C₂₀H₂₀N₂O₅
• 分子量: 368.389
• InChiKey: QXUVXRXKFCGYHI-XIKOKIGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  88.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5R)-3-(furan-2-carbonyl)-5-methyl-N-(8-oxo-5,6,7,8-tetrahydronaphthalen-1-yl)oxazolidine-4-carboxamide 以 六甲基磷酰三胺 、 乙腈 为溶剂， 以13%的产率得到(1R,2S,5S,10R,11S)-syn-1-hydroxy-10-methyl-9,23-dioxa-7,13-diazahexacyclo[12.7.1.1.0^5,13.0^7,11.0^18,22]tricosa-3,14,16,18(22)-tetraene-6,12-dione
  参考文献：
  名称：

  Photoassisted Access to Enantiopure Conformationally Locked Ribofuranosylamines Spiro-Linked to Oxazolidino-Diketopiperazines.

  摘要：

  N-Furoylated L-threonine-, serine-, or cysteine-based aminoacetals are coupled with o-aminoketones or aldehydes to offer rapid access to diverse enantiopure polyheterocycles possessing conformationally locked aminoglycoside-containing molecular scaffolds. The key step involves photogeneration of azaxylylenes which undergo [4 + 4] or [4 + 2] cycloadditions to the tethered furoyl pendants.

  DOI：

  10.1021/co3001296
• 作为产物：
  描述：

  (4S,5R)-3-(furan-2-carbonyl)-5-methyloxazolidine-4-carboxylic acid 、 8-氨基-3,4-二氢萘-1(2H)-酮 在 N-羟基-7-氮杂苯并三氮唑 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以67%的产率得到(4S,5R)-3-(furan-2-carbonyl)-5-methyl-N-(8-oxo-5,6,7,8-tetrahydronaphthalen-1-yl)oxazolidine-4-carboxamide
  参考文献：
  名称：

  Photoassisted Access to Enantiopure Conformationally Locked Ribofuranosylamines Spiro-Linked to Oxazolidino-Diketopiperazines.

  摘要：

  N-Furoylated L-threonine-, serine-, or cysteine-based aminoacetals are coupled with o-aminoketones or aldehydes to offer rapid access to diverse enantiopure polyheterocycles possessing conformationally locked aminoglycoside-containing molecular scaffolds. The key step involves photogeneration of azaxylylenes which undergo [4 + 4] or [4 + 2] cycloadditions to the tethered furoyl pendants.

  DOI：

  10.1021/co3001296