tert-butyl N-[N'-[4-[[3-(6-bromo-1H-indol-3-yl)-2-oxopropanoyl]amino]butyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate | 1227931-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: tert-butyl N-[N'-[4-[[3-(6-bromo-1H-indol-3-yl)-2-oxopropanoyl]amino]butyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate
• CAS: 1227931-53-4
• 化学式: C₂₆H₃₆BrN₅O₆
• 分子量: 594.506
• InChiKey: UHONNLYKSKBACE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[N'-[4-[[3-(6-bromo-1H-indol-3-yl)-2-oxopropanoyl]amino]butyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 生成 、 tert-butyl N-[N'-[4-[[(2R,3R,4S)-1-[4-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]butyl]-3-(6-bromo-1H-indol-3-yl)-4-[(6-bromo-1H-indol-3-yl)methyl]-2,4-dihydroxy-5-oxopyrrolidine-2-carbonyl]amino]butyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate
  参考文献：
  名称：

  Synthesis of (±)-Eusynstyelamide A

  摘要：

  The synthesis of (+/-)-eusynstyelamide A has been accomplished in six steps in 13% overall yield from 6-bromoindole, methyl glycidate, and Boc-protected agmatine. If oxygen is carefully excluded from the reaction, the key NaOH-catalyzed aldol dimerization of the alpha-ketoamide proceeded efficiently to give Boc-protected eusynstyelamide A.

  DOI：

  10.1021/ol100896n
• 作为产物：
  描述：

  tert-butyl N-[N'-[4-[[3-(6-bromo-1H-indol-3-yl)-2-hydroxypropanoyl]amino]butyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate 在 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.0h， 以14%的产率得到tert-butyl N-[N'-[4-[[3-(6-bromo-1H-indol-3-yl)-2-oxopropanoyl]amino]butyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate
  参考文献：
  名称：

  Synthesis of (±)-Eusynstyelamide A

  摘要：

  The synthesis of (+/-)-eusynstyelamide A has been accomplished in six steps in 13% overall yield from 6-bromoindole, methyl glycidate, and Boc-protected agmatine. If oxygen is carefully excluded from the reaction, the key NaOH-catalyzed aldol dimerization of the alpha-ketoamide proceeded efficiently to give Boc-protected eusynstyelamide A.

  DOI：

  10.1021/ol100896n

文献信息

• Synthesis of (±)-Eusynstyelamide A
  作者：Olga V. Barykina、Barry B. Snider

  DOI：10.1021/ol100896n

  日期：2010.6.4

  The synthesis of (+/-)-eusynstyelamide A has been accomplished in six steps in 13% overall yield from 6-bromoindole, methyl glycidate, and Boc-protected agmatine. If oxygen is carefully excluded from the reaction, the key NaOH-catalyzed aldol dimerization of the alpha-ketoamide proceeded efficiently to give Boc-protected eusynstyelamide A.