3-(4-hydroxy-2-methoxyphenyl)-N-methoxy-N-methyl-2-(2,2,2-trifluoroacetamido)propanamide | 1265501-12-9

• 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: 3-(4-hydroxy-2-methoxyphenyl)-N-methoxy-N-methyl-2-(2,2,2-trifluoroacetamido)propanamide
• 英文别名: 3-(4-hydroxy-2-methoxyphenyl)-N-methoxy-N-methyl-2-[(2,2,2-trifluoroacetyl)amino]propanamide
• CAS: 1265501-12-9
• 化学式: C₁₄H₁₇F₃N₂O₅
• 分子量: 350.295
• InChiKey: KOBYGXKDNNHNCY-UHFFFAOYSA-N

物化性质

• 熔点：
  170-172 °C
• 密度：
  1.343±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxy-2-methoxyphenyl)-N-methoxy-N-methyl-2-(2,2,2-trifluoroacetamido)propanamide 在 碘苯二乙酸 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 (6S)-N,7-dimethoxy-N-methyl-9-oxo-2-(trifluoromethyl)-1-oxa-3-azaspiro[5.5]undeca-2,7,10-triene-4-carboxamide 、 (6S)-N,7-dimethoxy-N-methyl-9-oxo-2-(trifluoromethyl)-1-oxa-3-azaspiro[5.5]undeca-2,7,10-triene-4-carboxamide
  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：

  C₂₁H₃₁NO₈ 在 lithium hydrochloride monohydrate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 38.0h， 生成 3-(4-hydroxy-2-methoxyphenyl)-N-methoxy-N-methyl-2-(2,2,2-trifluoroacetamido)propanamide
  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,