tert-butyl N-[2-[[(E)-2-(4-hydroxyphenyl)ethenyl]amino]-2-oxoethyl]carbamate | 262601-04-7

• 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 N-[2-[[(E)-2-(4-hydroxyphenyl)ethenyl]amino]-2-oxoethyl]carbamate
• CAS: 262601-04-7
• 化学式: C₁₅H₂₀N₂O₄
• 分子量: 292.335
• InChiKey: SKMIYJQWVHYYPJ-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[2-[[(E)-2-(4-hydroxyphenyl)ethenyl]amino]-2-oxoethyl]carbamate 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 吡啶 、 二氯甲烷 、 乙腈 为溶剂， 反应 13.17h， 生成 (E)-5-[[bis[[(1,1-dimethoxy)carbonyl]amino]methylene]amino]-2-hydroxypentanoyl-N-[2-(4-acetoxyphenyl)ethenyl]glycinamide
  参考文献：
  名称：

  Total Syntheses of (±)-Anchinopeptolide D and (±)-Cycloanchinopeptolide D

  摘要：

  The first synthesis of (+/-)-anchinopeptolide D (4) has been accomplished in seven steps in 10% overall yield from octopamine hydrochloride (17), N-(Boc)glycine (16), and 5-amino-2-hydroxypentanoic acid (22). The key step is the aldol dimerization and hemiaminal formation of cr-keto amide 26, which gives primarily protected anchinopeptolide D 27 under kinetically controlled conditions. Cycloanchinopeptolide D (31) has been prepared by the unprecedented head-to-head photodimerization of the two hydroxystyrylamides of 4 using the hydrophobic effect in water to force the two side chains into close proximity so that [2 + 2] cycloaddition is faster than trans to cis double bond isomerization. Coupling of amine 21 with pyroglutamic acid affords the naturally occurring tripeptide 35, which had been assigned glutamic acid structure 34.

  DOI：

  10.1021/jo991454l
• 作为产物：
  描述：

  章胺盐酸盐 在 potassium carbonate 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 tert-butyl N-[2-[[(E)-2-(4-hydroxyphenyl)ethenyl]amino]-2-oxoethyl]carbamate
  参考文献：
  名称：

  Total Syntheses of (±)-Anchinopeptolide D and (±)-Cycloanchinopeptolide D

  摘要：

  The first synthesis of (+/-)-anchinopeptolide D (4) has been accomplished in seven steps in 10% overall yield from octopamine hydrochloride (17), N-(Boc)glycine (16), and 5-amino-2-hydroxypentanoic acid (22). The key step is the aldol dimerization and hemiaminal formation of cr-keto amide 26, which gives primarily protected anchinopeptolide D 27 under kinetically controlled conditions. Cycloanchinopeptolide D (31) has been prepared by the unprecedented head-to-head photodimerization of the two hydroxystyrylamides of 4 using the hydrophobic effect in water to force the two side chains into close proximity so that [2 + 2] cycloaddition is faster than trans to cis double bond isomerization. Coupling of amine 21 with pyroglutamic acid affords the naturally occurring tripeptide 35, which had been assigned glutamic acid structure 34.

  DOI：

  10.1021/jo991454l

文献信息

• Total Syntheses of (±)-Anchinopeptolide D and (±)-Cycloanchinopeptolide D
  作者：Barry B. Snider、Fengbin Song、Bruce M. Foxman

  DOI：10.1021/jo991454l

  日期：2000.2.1

  The first synthesis of (+/-)-anchinopeptolide D (4) has been accomplished in seven steps in 10% overall yield from octopamine hydrochloride (17), N-(Boc)glycine (16), and 5-amino-2-hydroxypentanoic acid (22). The key step is the aldol dimerization and hemiaminal formation of cr-keto amide 26, which gives primarily protected anchinopeptolide D 27 under kinetically controlled conditions. Cycloanchinopeptolide D (31) has been prepared by the unprecedented head-to-head photodimerization of the two hydroxystyrylamides of 4 using the hydrophobic effect in water to force the two side chains into close proximity so that [2 + 2] cycloaddition is faster than trans to cis double bond isomerization. Coupling of amine 21 with pyroglutamic acid affords the naturally occurring tripeptide 35, which had been assigned glutamic acid structure 34.