(2R,3aR,3S,6R)-hexahydro-6-[(1S)-2,2-diphenylcyclopentyloxy]isoxazolo[2,3-b][1,2]oxazine-2,3-dicarboxylic acid dimethyl ester | 206433-94-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3aR,3S,6R)-hexahydro-6-[(1S)-2,2-diphenylcyclopentyloxy]isoxazolo[2,3-b][1,2]oxazine-2,3-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl (2R,3R,3aR,6R)-6-[(1S)-2,2-diphenylcyclopentyl]oxy-2,3,3a,4,5,6-hexahydro-[1,2]oxazolo[2,3-b]oxazine-2,3-dicarboxylate
• CAS: 206433-94-5
• 化学式: C₂₇H₃₁NO₇
• 分子量: 481.546
• InChiKey: MSBFKTNXTGSSJZ-KEJFTWOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3aR,3S,6R)-hexahydro-6-[(1S)-2,2-diphenylcyclopentyloxy]isoxazolo[2,3-b][1,2]oxazine-2,3-dicarboxylic acid dimethyl ester 在 Raney nickel W-2 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、1.24 MPa 条件下， 反应 48.0h， 以53%的产率得到[1R,2R,7aR]-hexahydro-2-hydroxy-3-oxo-1H-pyrrolizine-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Tandem [4 + 2]/[3 + 2] Cycloadditions with Nitroethylene

  摘要：

  The simplest nitroalkene, nitroethylene, undergoes Lewis acid-promoted [4 + 2] cycloaddition with chiral vinyl ethers to afford cyclic nitronates with high diastereoselectivity. The resulting cyclic nitronates react with electron deficient alkenes to effect a face selective [3 + 2] cycloaddition. The origin of stereocontrol in the [3 + 2] cycloaddition is due to the single ring substituent, a remote acetal center. The scope and limitations of the use of nitroethylene as a 4 pi component in Lewis acid-promoted cycloadditions are documented and discussed. Additionally, concise syntheses of the pyrrolizidine alkaloids (+)-macronecine and (+)-petasinecine are presented.

  DOI：

  10.1021/jo972280f
• 作为产物：
  描述：

  [(2S)-2-ethenoxy-1-phenylcyclopentyl]benzene 在 甲基铝双(2,6-二苯基苯酚) 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 (2R,3aR,3S,6R)-hexahydro-6-[(1S)-2,2-diphenylcyclopentyloxy]isoxazolo[2,3-b][1,2]oxazine-2,3-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Tandem [4 + 2]/[3 + 2] Cycloadditions with Nitroethylene

  摘要：

  The simplest nitroalkene, nitroethylene, undergoes Lewis acid-promoted [4 + 2] cycloaddition with chiral vinyl ethers to afford cyclic nitronates with high diastereoselectivity. The resulting cyclic nitronates react with electron deficient alkenes to effect a face selective [3 + 2] cycloaddition. The origin of stereocontrol in the [3 + 2] cycloaddition is due to the single ring substituent, a remote acetal center. The scope and limitations of the use of nitroethylene as a 4 pi component in Lewis acid-promoted cycloadditions are documented and discussed. Additionally, concise syntheses of the pyrrolizidine alkaloids (+)-macronecine and (+)-petasinecine are presented.

  DOI：

  10.1021/jo972280f

文献信息

• Tandem [4 + 2]/[3 + 2] Cycloadditions with Nitroethylene
  作者：Scott E. Denmark、Alexander R. Hurd

  DOI：10.1021/jo972280f

  日期：1998.5.1

  The simplest nitroalkene, nitroethylene, undergoes Lewis acid-promoted [4 + 2] cycloaddition with chiral vinyl ethers to afford cyclic nitronates with high diastereoselectivity. The resulting cyclic nitronates react with electron deficient alkenes to effect a face selective [3 + 2] cycloaddition. The origin of stereocontrol in the [3 + 2] cycloaddition is due to the single ring substituent, a remote acetal center. The scope and limitations of the use of nitroethylene as a 4 pi component in Lewis acid-promoted cycloadditions are documented and discussed. Additionally, concise syntheses of the pyrrolizidine alkaloids (+)-macronecine and (+)-petasinecine are presented.