tert-butyl 3-(4-hydroxy-2-methoxyphenyl)-1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate | 1265501-11-8

• 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: tert-butyl 3-(4-hydroxy-2-methoxyphenyl)-1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate
• 英文别名: tert-butyl N-[3-(4-hydroxy-2-methoxyphenyl)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl]carbamate
• CAS: 1265501-11-8
• 化学式: C₁₇H₂₆N₂O₆
• 分子量: 354.403
• InChiKey: VVVSOEXTZGZCNH-UHFFFAOYSA-N

物化性质

• 熔点：
  200-203 °C
• 密度：
  1.180±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(4-hydroxy-2-methoxyphenyl)-1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate 在 4-二甲氨基吡啶 、 碘苯二乙酸 、 cesium fluoride 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.17h， 生成 (2E,4E)-N-(6-hydroxy-8-methoxy-2-oxo-2H-chromen-3-yl)hexa-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：

  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 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 30.0h， 生成 tert-butyl 3-(4-hydroxy-2-methoxyphenyl)-1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate
  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,