<1S-(1α,2α,4β,5α,6α)>-5-bromo-7-(p-methoxyphenyl)-2-methyl-3-oxa-4-phenyl-7-azabicyclo<4.2.0>octan-8-one | 143288-89-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: <1S-(1α,2α,4β,5α,6α)>-5-bromo-7-(p-methoxyphenyl)-2-methyl-3-oxa-4-phenyl-7-azabicyclo<4.2.0>octan-8-one
• 英文别名: (1S,2R,4R,5S,6R)-5-bromo-7-(4-methoxyphenyl)-2-methyl-4-phenyl-3-oxa-7-azabicyclo[4.2.0]octan-8-one
• CAS: 143288-89-5
• 化学式: C₂₀H₂₀BrNO₃
• 分子量: 402.288
• InChiKey: KVLSBKNDGIIJQV-DCCCRPSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <1S-(1α,2α,4β,5α,6α)>-5-bromo-7-(p-methoxyphenyl)-2-methyl-3-oxa-4-phenyl-7-azabicyclo<4.2.0>octan-8-one 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 反应 1.0h， 以57%的产率得到<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：

  <3S,4S(E)>-3-<1(R)-hydroxyethyl>-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以17%的产率得到<1S-(1α,2α,4α,5β,6α)>-5-bromo-7-(p-methoxyphenyl)-2-methyl-3-oxa-4-phenyl-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

文献信息

• C-Aryl glycosides: electrophile-initiated cyclizations of 6-aryl-5-hexen-2-ols
  作者：David J. Hart、Vincent Leroy、Gregory H. Merriman、David G. J. Young

  DOI：10.1021/jo00047a020

  日期：1992.10

  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.