3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylethynyl)-4,5-dihydro-isoxazole | 156766-10-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylethynyl)-4,5-dihydro-isoxazole
• CAS: 156766-10-8
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: QTLITLIWSLNMGO-VIFPVBQESA-N

物化性质

• 沸点：
  272.1±50.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  40.05
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylethynyl)-4,5-dihydro-isoxazole 在 Lindlar's catalyst 喹啉 、 氢气 、 碘 作用下， 生成 3-[(E)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethenyl]-4,5-dihydro-1,2-oxazole
  参考文献：
  名称：

  Synthesis of l-Daunosamine Derivatives on the Basis of the Asymmetric Dihydroxylation of 3-((E)-1-Propenyl)-4,5-dihydroisoxazole

  摘要：

  Methyl L-N,O-diacetyldaunosaminide was prepared from 3-nitro-4,5-dihydroisoxazole in 8.5% overall yield. A key step in the synthesis involved the AD reaction of (E)-3-(1-propenyl)-4,5-dihydroisoxazole (2b), affording the corresponding diol in 76% yield (92% ee). A second key step involved reductive cleavage of the dihydroisoxazole 4a and subsequent N-acetylation to afford separable diastereomeric gamma-(acetylamino)alcohols 7a and 8a in 62% yield (72:28, 7a/8a). Swern oxidation of 7a and subsequent methanolysis followed by acetylation provided methyl L-N,O-diacetyldaunosaminide as an anomeric mixture. The AD reactions of chiral alkenyl dihydroisoxazole 16 with (DHQ)(2)-PHAL and (DHQD)(2)-PHAL afforded diastereomeric diol products, isolated as the acetates 18 and 19 (98:2 and 5:95 ratios, respectively, depending on the chiral auxiliary).

  DOI：

  10.1021/jo962293d
• 作为产物：
  描述：

  3-硝基-4,5-二氢异噁唑 、 (S)-4-ethynyl-2,2-dimethyl-1,3-dioxolane 在 正丁基锂 作用下， 生成 3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylethynyl)-4,5-dihydro-isoxazole
  参考文献：
  名称：

  Synthesis of l-Daunosamine Derivatives on the Basis of the Asymmetric Dihydroxylation of 3-((E)-1-Propenyl)-4,5-dihydroisoxazole

  摘要：

  Methyl L-N,O-diacetyldaunosaminide was prepared from 3-nitro-4,5-dihydroisoxazole in 8.5% overall yield. A key step in the synthesis involved the AD reaction of (E)-3-(1-propenyl)-4,5-dihydroisoxazole (2b), affording the corresponding diol in 76% yield (92% ee). A second key step involved reductive cleavage of the dihydroisoxazole 4a and subsequent N-acetylation to afford separable diastereomeric gamma-(acetylamino)alcohols 7a and 8a in 62% yield (72:28, 7a/8a). Swern oxidation of 7a and subsequent methanolysis followed by acetylation provided methyl L-N,O-diacetyldaunosaminide as an anomeric mixture. The AD reactions of chiral alkenyl dihydroisoxazole 16 with (DHQ)(2)-PHAL and (DHQD)(2)-PHAL afforded diastereomeric diol products, isolated as the acetates 18 and 19 (98:2 and 5:95 ratios, respectively, depending on the chiral auxiliary).

  DOI：

  10.1021/jo962293d

文献信息

• Diastereocontrol in the asymmetric dihydroxylation of chiral 3-alkenyl-4,5-dihydroisoxazoles
  作者：Peter A. Wade、Damien T. Cole、Stephen G. D'Ambrosio

  DOI：10.1016/0040-4039(94)88160-x

  日期：1994.1

  Catalytic asymmetric dihydroxylation of 4 afforded virtually one diastereomer using (DHQD)(2)-PHAL as a chiral auxiliary (matched pair; 96% d.e.); the other diastereomer was heavily predominant with (DHQ)(2)-PHAL as the chiral auxiliary (mismatched pair; 90% d.e.).