(2S,3aS,7S)-2-(hydroxymethyl)-7-phenyl-3,3a,6,7-tetrahydro-2H-[1,2]oxazolo[3,2-c][1,4]oxazin-4-one | 221284-61-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3aS,7S)-2-(hydroxymethyl)-7-phenyl-3,3a,6,7-tetrahydro-2H-[1,2]oxazolo[3,2-c][1,4]oxazin-4-one
• CAS: 221284-61-3
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: QCGPKVPGBDFSFU-SDDRHHMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (2S,3aS,7S)-2-(hydroxymethyl)-7-phenyl-3,3a,6,7-tetrahydro-2H-[1,2]oxazolo[3,2-c][1,4]oxazin-4-one 在 palladium hydroxide - carbon 盐酸 、 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 生成 (3S,5S)-3-benzyloxycarbonylamino-5-hydroxy-γ-lactone
  参考文献：
  名称：

  Chelation controlled 1,3-dipolar cycloaddition of 5,6-Dihydro-5-phenyl-1,4-oxazin-2-one N-oxide with allyl alcohols: A short-step synthesis of clavalanine intermediate

  摘要：

  (R)-5, 6-Dihydro-5-phenyl-1,4-oxazin-2-one N-oxide {(R)-2} reacts with allyl alcohols 3a-c in the presence of magnesium bromide from the less hindered face via exo-mode to afford corresponding cycloadducts 4a-c with excellent stereoselection. Treatment of (R)-2 with three equivalents of racemic secondary allyl alcohols 3d-g under the same conditions causes partial kinetic resolution to give 4d-g as main products among eight possible stereoisomers. Cycloadduct ent-4a from (S)-2 and 3a was converted directly to g-lactone 6, which is known as the key synthetic intermediate of antibiotic clavalanine. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02476-9
• 作为产物：
  描述：

  烯丙醇 、 (5S)-5,6-dihydro-5-phenyl-2H-1,4-oxazin-2-one-N-oxide 在 magnesium bromide ethyl etherate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以89%的产率得到(2S,3aS,7S)-2-(hydroxymethyl)-7-phenyl-3,3a,6,7-tetrahydro-2H-[1,2]oxazolo[3,2-c][1,4]oxazin-4-one
  参考文献：
  名称：

  Chelation controlled 1,3-dipolar cycloaddition of 5,6-Dihydro-5-phenyl-1,4-oxazin-2-one N-oxide with allyl alcohols: A short-step synthesis of clavalanine intermediate

  摘要：

  (R)-5, 6-Dihydro-5-phenyl-1,4-oxazin-2-one N-oxide {(R)-2} reacts with allyl alcohols 3a-c in the presence of magnesium bromide from the less hindered face via exo-mode to afford corresponding cycloadducts 4a-c with excellent stereoselection. Treatment of (R)-2 with three equivalents of racemic secondary allyl alcohols 3d-g under the same conditions causes partial kinetic resolution to give 4d-g as main products among eight possible stereoisomers. Cycloadduct ent-4a from (S)-2 and 3a was converted directly to g-lactone 6, which is known as the key synthetic intermediate of antibiotic clavalanine. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02476-9

文献信息

• Chelation controlled 1,3-dipolar cycloaddition of 5,6-Dihydro-5-phenyl-1,4-oxazin-2-one N-oxide with allyl alcohols: A short-step synthesis of clavalanine intermediate
  作者：Osamu Tamura、Takahiro Kuroki、Yuta Sakai、Jun-ichi Takizawa、Jun Yoshino、Yasuhiro Morita、Naka Mita、Kentoku Gotanda、Masanori Sakamoto

  DOI：10.1016/s0040-4039(98)02476-9

  日期：1999.1

  (R)-5, 6-Dihydro-5-phenyl-1,4-oxazin-2-one N-oxide (R)-2} reacts with allyl alcohols 3a-c in the presence of magnesium bromide from the less hindered face via exo-mode to afford corresponding cycloadducts 4a-c with excellent stereoselection. Treatment of (R)-2 with three equivalents of racemic secondary allyl alcohols 3d-g under the same conditions causes partial kinetic resolution to give 4d-g as main products among eight possible stereoisomers. Cycloadduct ent-4a from (S)-2 and 3a was converted directly to g-lactone 6, which is known as the key synthetic intermediate of antibiotic clavalanine. (C) 1999 Elsevier Science Ltd. All rights reserved.