4,5-dihydro-4-(phenylmethoxy)-3-isoxazolecarbonitrile | 171815-21-7

• 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: 4,5-dihydro-4-(phenylmethoxy)-3-isoxazolecarbonitrile
• 英文别名: 4-Phenylmethoxy-4,5-dihydro-1,2-oxazole-3-carbonitrile
• CAS: 171815-21-7
• 化学式: C₁₁H₁₀N₂O₂
• 分子量: 202.213
• InChiKey: SZPMXKHJMMYUPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  54.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5-dihydro-4-(phenylmethoxy)-3-isoxazolecarbonitrile 在 二异丁基氢化铝 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 4,5-dihydro-4-(phenylmethoxy)-3-isoxazolecarboxaldehyde
  参考文献：
  名称：

  2-Amino-2-deoxytetrose Derivatives. Preparation from 4,5-Dihydroisoxazoles via Reductive Cleavage

  摘要：

  The 4-alkoxy-3-nitro-4,5-dihydroisoxazoles 2a,b were prepared by condensation of nitromethane and chloroacetaldehyde, protection of the resulting nitroaldol Ic, and subsequent nitrosative cyclization. Multistep replacement of the nitro group of 2a,b by a 2-(1,3-dithiolanyl) group gave 7a,b. Reaction of 7b with lithium borohydride afforded reductive cleavage of the dihydroisoxazole ring to produce the open-chain diastereomeric amino alcohols 6a,b. A reproducible ratio of > 90: 10 6a/6b was obtained using freshly prepared hydride reagent. The amino alcohols were converted to the corresponding (R*,R*)-amide 6c and (R*,S*)-amide 6d which were chromatographically separated. The(R*,R*)-amide was transformed into the 2-amino-2-deoxythreose derivatives 11a,b and hence to 12 while the (R*,S*)-amide was similarly transformed to 2-amino-2-deoxyerythrose derivative 14a and its anomeric isomer 14b.

  DOI：

  10.1021/jo00125a015
• 作为产物：
  描述：

  <<1-(chloromethyl)-2-nitroethoxy>methyl>benzene 在 亚硝酸丙酯 、 sodium nitrite 作用下， 以 二甲基亚砜 为溶剂， 反应 4.42h， 生成 4,5-dihydro-4-(phenylmethoxy)-3-isoxazolecarbonitrile
  参考文献：
  名称：

  2-Amino-2-deoxytetrose Derivatives. Preparation from 4,5-Dihydroisoxazoles via Reductive Cleavage

  摘要：

  The 4-alkoxy-3-nitro-4,5-dihydroisoxazoles 2a,b were prepared by condensation of nitromethane and chloroacetaldehyde, protection of the resulting nitroaldol Ic, and subsequent nitrosative cyclization. Multistep replacement of the nitro group of 2a,b by a 2-(1,3-dithiolanyl) group gave 7a,b. Reaction of 7b with lithium borohydride afforded reductive cleavage of the dihydroisoxazole ring to produce the open-chain diastereomeric amino alcohols 6a,b. A reproducible ratio of > 90: 10 6a/6b was obtained using freshly prepared hydride reagent. The amino alcohols were converted to the corresponding (R*,R*)-amide 6c and (R*,S*)-amide 6d which were chromatographically separated. The(R*,R*)-amide was transformed into the 2-amino-2-deoxythreose derivatives 11a,b and hence to 12 while the (R*,S*)-amide was similarly transformed to 2-amino-2-deoxyerythrose derivative 14a and its anomeric isomer 14b.

  DOI：

  10.1021/jo00125a015

文献信息

• 2-Amino-2-deoxytetrose Derivatives. Preparation from 4,5-Dihydroisoxazoles via Reductive Cleavage
  作者：Peter A. Wade、Stephen G. D'Ambrosio、David T. Price

  DOI：10.1021/jo00125a015

  日期：1995.10

  The 4-alkoxy-3-nitro-4,5-dihydroisoxazoles 2a,b were prepared by condensation of nitromethane and chloroacetaldehyde, protection of the resulting nitroaldol Ic, and subsequent nitrosative cyclization. Multistep replacement of the nitro group of 2a,b by a 2-(1,3-dithiolanyl) group gave 7a,b. Reaction of 7b with lithium borohydride afforded reductive cleavage of the dihydroisoxazole ring to produce the open-chain diastereomeric amino alcohols 6a,b. A reproducible ratio of > 90: 10 6a/6b was obtained using freshly prepared hydride reagent. The amino alcohols were converted to the corresponding (R*,R*)-amide 6c and (R*,S*)-amide 6d which were chromatographically separated. The(R*,R*)-amide was transformed into the 2-amino-2-deoxythreose derivatives 11a,b and hence to 12 while the (R*,S*)-amide was similarly transformed to 2-amino-2-deoxyerythrose derivative 14a and its anomeric isomer 14b.