3-(4-hydroxy-2-methoxyphenyl)-N-methoxy-N-methyl-2-(2-(trimethylsilyl)ethylsulfonamino)propanamide | 1140924-29-3

• 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-(trimethylsilyl)ethylsulfonamino)propanamide
• 英文别名: 3-(4-hydroxy-2-methoxyphenyl)-N-methoxy-N-methyl-2-(2-trimethylsilylethylsulfonylamino)propanamide
• CAS: 1140924-29-3
• 化学式: C₁₇H₃₀N₂O₆SSi
• 分子量: 418.587
• InChiKey: XYLJZIPQIOYIDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxy-2-methoxyphenyl)-N-methoxy-N-methyl-2-(2-(trimethylsilyl)ethylsulfonamino)propanamide 在 4-二甲氨基吡啶 、 碘苯二乙酸 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.17h， 生成 (2E,4E)-N-(6-methoxy-2,8-dioxo-1-oxaspiro[4.5]deca-6,9-dien-3-yl)-N-(2-(trimethylsilyl)ethylsulfonyl)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 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 40.0h， 生成 3-(4-hydroxy-2-methoxyphenyl)-N-methoxy-N-methyl-2-(2-(trimethylsilyl)ethylsulfonamino)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

• Deprotection of Homoallyl (^hAllyl) Derivatives of Phenols, Alcohols, Acids, and Amines
  作者：Bruce H. Lipshutz、Subir Ghorai、Wendy Wen Yi Leong

  DOI：10.1021/jo900012z

  日期：2009.4.3

  The homoallyl moiety, (h)Allyl, is presented as a general protecting group for several functionalities. It can be chemoselectively removed via a sequential, one-pot cross-metathesis/elimination sequence.
• 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,