(+/-)-(2E,4E)-N-((S)-3-((1S,2S,6R)-2-hydroxy-3-methoxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl)-5-(trimethylsilyl)penta-2,4-dienamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+/-)-(2E,4E)-N-((S)-3-((1S,2S,6R)-2-hydroxy-3-methoxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl)-5-(trimethylsilyl)penta-2,4-dienamide
• 英文别名: (2E,4E)-N-[(2R)-3-[(1R,2R,6S)-2-hydroxy-3-methoxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-1-oxo-1-pyrrolidin-1-ylpropan-2-yl]-5-trimethylsilylpenta-2,4-dienamide
• 化学式: C₂₂H₃₂N₂O₆Si
• 分子量: 448.591
• InChiKey: VIKGWMQYGRWNGS-ZFYMGISMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.08
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-(2E,4E)-N-((S)-3-((1S,2S,6R)-2-hydroxy-3-methoxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl)-5-(trimethylsilyl)penta-2,4-dienamide 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 9.0h， 生成 (+/-)-(2E,4E)-N-((1S,2S,4'S,5S,6S)-5-hydroxy-3-methoxy-5'-oxo-4',5'-dihydro-3'H-7-oxaspiro[bicyclo[4.1.0]hept[3]ene-2,2'-furan]-4'-yl)-5-(trimethylsilyl)penta-2,4-dienamide
  参考文献：
  名称：

  A Strategy for the Late-Stage Divergent Syntheses of Scyphostatin Analogues

  摘要：

  This account details the synthesis of two scyphostatin analogues exhibiting a reactive polar epoxycyclohexenone core and various amide side chains outfitted for late-stage chemical derivatization into the desirable lipophilic tails. Our efforts highlight a key ipso-dearomatization process and provide new insights regarding the incompatibility and orthogonal reactivity of scyphostatin's functional groups. We further showcase the utility of resorcinol derived 2,5-cyclohexadienones as synthetic platforms capable of participating in selective chemical reactivity, and we further demonstrate their potential for rapid elaboration into complex structural motifs,

  DOI：

  10.1021/jo102327e
• 作为产物：
  描述：

  (S)-methyl 3-(4-hydroxy-2-methoxy)-2-((2E,4E)-5-(trimethylsilyl)penta-2,4-dienamido)propanoate 在 lithium hydrochloride monohydrate 、 1,5-二氮杂双环[4.3.0]壬-5-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 21.5h， 生成 (+/-)-(2E,4E)-N-((S)-3-((1S,2S,6R)-2-hydroxy-3-methoxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl)-5-(trimethylsilyl)penta-2,4-dienamide
  参考文献：
  名称：

  A Strategy for the Late-Stage Divergent Syntheses of Scyphostatin Analogues

  摘要：

  This account details the synthesis of two scyphostatin analogues exhibiting a reactive polar epoxycyclohexenone core and various amide side chains outfitted for late-stage chemical derivatization into the desirable lipophilic tails. Our efforts highlight a key ipso-dearomatization process and provide new insights regarding the incompatibility and orthogonal reactivity of scyphostatin's functional groups. We further showcase the utility of resorcinol derived 2,5-cyclohexadienones as synthetic platforms capable of participating in selective chemical reactivity, and we further demonstrate their potential for rapid elaboration into complex structural motifs,

  DOI：

  10.1021/jo102327e

文献信息

• A Strategy for the Late-Stage Divergent Syntheses of Scyphostatin Analogues
  作者：Jacob Y. Cha、G. Leslie Burnett、Yaodong Huang、Jarrod B. Davidson、Thomas R. R. Pettus

  DOI：10.1021/jo102327e

  日期：2011.3.4

  This account details the synthesis of two scyphostatin analogues exhibiting a reactive polar epoxycyclohexenone core and various amide side chains outfitted for late-stage chemical derivatization into the desirable lipophilic tails. Our efforts highlight a key ipso-dearomatization process and provide new insights regarding the incompatibility and orthogonal reactivity of scyphostatin's functional groups. We further showcase the utility of resorcinol derived 2,5-cyclohexadienones as synthetic platforms capable of participating in selective chemical reactivity, and we further demonstrate their potential for rapid elaboration into complex structural motifs,