[(1S)-1-[(3S,4S)-1-(4-methoxyphenyl)-2-oxo-4-[(E)-2-phenylethenyl]azetidin-3-yl]ethyl] formate | 143288-86-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: [(1S)-1-[(3S,4S)-1-(4-methoxyphenyl)-2-oxo-4-[(E)-2-phenylethenyl]azetidin-3-yl]ethyl] formate
• CAS: 143288-86-2
• 化学式: C₂₁H₂₁NO₄
• 分子量: 351.402
• InChiKey: ULILPRNJHYOJER-DYSOGMQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(1S)-1-[(3S,4S)-1-(4-methoxyphenyl)-2-oxo-4-[(E)-2-phenylethenyl]azetidin-3-yl]ethyl] formate 在 sodium hydroxide 、 偶氮二异丁腈 、 三正丁基氢锡 、 对甲苯磺酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 <1S-(1α,2α,4β,6α)>-7-(p-methoxyphenyl)-2-methyl-4-phenyl-3-oxa-7-azabicyclo<4.2.0>octan-8-one
  参考文献：
  名称：

  C-Aryl glycosides: electrophile-initiated cyclizations of 6-aryl-5-hexen-2-ols

  摘要：

  An approach to the synthesis of C-aryl glycosides is described. Treatment of beta-lactam 9 with N-bromosuccinimide (NBS) or N-iodosuccinimide (NIS) afforded trans-2,6-disubstituted pyrans 11a and 11b. Treatment of 9 with phenylselenenyl chloride (PhSeCl) or N-(phenylselenenyl)phthalimide (N-PSP) gave 11c and cis-2,6-disubstituted pyran 12c in different ratios depending on the reaction conditions. Treatment of beta-lactam 10 with NBS, NIS, PhSeCl, or N-PSP gave mixtures of pyrans 16 and 17. Treatment of unsaturated alcohol 24a with PhSeCl gave pyran 23a. Conversion of 23a to virenose analog 22, a C-aryl glycoside related to the chrysomycins, was accomplished using a selenoxide elimination-osmium tetraoxide oxidation sequence.

  DOI：

  10.1021/jo00047a020
• 作为产物：
  描述：

  甲酸 、 (3S,4S)-3-<(S)-1-hydroxyethyl>-1-p-methoxyphenyl-4-styrylazetidin-2-one 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以500 mg的产率得到[(1S)-1-[(3S,4S)-1-(4-methoxyphenyl)-2-oxo-4-[(E)-2-phenylethenyl]azetidin-3-yl]ethyl] formate
  参考文献：
  名称：

  C-Aryl glycosides: electrophile-initiated cyclizations of 6-aryl-5-hexen-2-ols

  摘要：

  An approach to the synthesis of C-aryl glycosides is described. Treatment of beta-lactam 9 with N-bromosuccinimide (NBS) or N-iodosuccinimide (NIS) afforded trans-2,6-disubstituted pyrans 11a and 11b. Treatment of 9 with phenylselenenyl chloride (PhSeCl) or N-(phenylselenenyl)phthalimide (N-PSP) gave 11c and cis-2,6-disubstituted pyran 12c in different ratios depending on the reaction conditions. Treatment of beta-lactam 10 with NBS, NIS, PhSeCl, or N-PSP gave mixtures of pyrans 16 and 17. Treatment of unsaturated alcohol 24a with PhSeCl gave pyran 23a. Conversion of 23a to virenose analog 22, a C-aryl glycoside related to the chrysomycins, was accomplished using a selenoxide elimination-osmium tetraoxide oxidation sequence.

  DOI：

  10.1021/jo00047a020