prop-2-enyl 2-[(3S,10R,13E,16S)-16-[(2S,3R,4S)-4-bromo-3-formyloxy-4-phenylbutan-2-yl]-10-[(3-chloro-4-methoxyphenyl)methyl]-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diazacyclohexadec-13-en-3-yl]acetate | 1248798-86-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: prop-2-enyl 2-[(3S,10R,13E,16S)-16-[(2S,3R,4S)-4-bromo-3-formyloxy-4-phenylbutan-2-yl]-10-[(3-chloro-4-methoxyphenyl)methyl]-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diazacyclohexadec-13-en-3-yl]acetate
• CAS: 1248798-86-8
• 化学式: C₃₈H₄₄BrClN₂O₁₁
• 分子量: 820.131
• InChiKey: JFLIPLCFEMJROR-QFTAXSJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  53
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  173
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  prop-2-enyl 2-[(3S,10R,13E,16S)-16-[(2S,3R,4S)-4-bromo-3-formyloxy-4-phenylbutan-2-yl]-10-[(3-chloro-4-methoxyphenyl)methyl]-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diazacyclohexadec-13-en-3-yl]acetate 在 potassium hydrogencarbonate 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 45.5h， 以11 mg的产率得到prop-2-enyl 2-[(3S,10R,13E,16S)-10-[(3-chloro-4-methoxyphenyl)methyl]-6,6-dimethyl-2,5,9,12-tetraoxo-16-[(1S)-1-[(2R,3R)-3-phenyloxiran-2-yl]ethyl]-1,4-dioxa-8,11-diazacyclohexadec-13-en-3-yl]acetate
  参考文献：
  名称：

  Approaches for the Synthesis of Functionalized Cryptophycins

  摘要：

  The first syntheses of bioactive cryptophycins functionalized at unit ID were accomplished ina one-pot Staudinger reduction/cyclization step An a/ado precursor for the lower part of the backbone was introduced to minimize protective group chemistry and enable a very convenient synthesis of cryptophycin-52 and unit D eryptophycin analogues containing an ester or a free carboxylic acid for bioconjugations Both new cryptophycin derivatives show high biological activity in cytotoxicity assays

  DOI：

  10.1021/jo101563s
• 作为产物：
  描述：

  在 乙酰溴 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 prop-2-enyl 2-[(3S,10R,13E,16S)-16-[(2S,3R,4S)-4-bromo-3-formyloxy-4-phenylbutan-2-yl]-10-[(3-chloro-4-methoxyphenyl)methyl]-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diazacyclohexadec-13-en-3-yl]acetate
  参考文献：
  名称：

  Approaches for the Synthesis of Functionalized Cryptophycins

  摘要：

  The first syntheses of bioactive cryptophycins functionalized at unit ID were accomplished ina one-pot Staudinger reduction/cyclization step An a/ado precursor for the lower part of the backbone was introduced to minimize protective group chemistry and enable a very convenient synthesis of cryptophycin-52 and unit D eryptophycin analogues containing an ester or a free carboxylic acid for bioconjugations Both new cryptophycin derivatives show high biological activity in cytotoxicity assays

  DOI：

  10.1021/jo101563s