tert-butyl 3-(3-(allyloxy)-3-oxopropyl)-4-(2-methoxyvinyl)-1H-pyrrole-2-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: tert-butyl 3-(3-(allyloxy)-3-oxopropyl)-4-(2-methoxyvinyl)-1H-pyrrole-2-carboxylate
• 英文别名: tert-butyl 4-[(E)-2-methoxyethenyl]-3-(3-oxo-3-prop-2-enoxypropyl)-1H-pyrrole-2-carboxylate
• 化学式: C₁₈H₂₅NO₅
• 分子量: 335.4
• InChiKey: AXNHBCGPVRFQHO-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  t-butyl 3-[2-(allyloxycarbonyl)ethyl]-4-methyl-1H-pyrrole-2-carboxylate 在 正丁基锂 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 甲苯 为溶剂， 反应 49.17h， 生成 tert-butyl 3-(3-(allyloxy)-3-oxopropyl)-4-(2-methoxyvinyl)-1H-pyrrole-2-carboxylate 、 tert-butyl 3-(3-(allyloxy)-3-oxopropyl)-4-(2-methoxyvinyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  One-Carbon Homologation of Pyrrole Carboxaldehyde via Wittig Reaction and Mild Hydrolysis of Vinyl Ether – toward the Synthesis of a Sterically Locked Phytochrome Chromophore

  摘要：

  Mild hydrolysis of vinyl ether derived from a pyrrole carboxaldehyde corresponding to the B,C-ring component of phytochromobilin chromophore was achieved by treatment with oxalyl chloride in chloroform in the presence of water and ethanol to afford a one-carbon homologated aldehyde. This aldehyde was applied to the synthesis of the sterically locked 15E-anti CD-ring component of the chromophore. Furthermore, the aldehyde could be converted to the intermediate for the sterically locked 5Z-anti AB-ring component.

  DOI：

  10.3987/com-14-13157

文献信息

• One-Carbon Homologation of Pyrrole Carboxaldehyde via Wittig Reaction and Mild Hydrolysis of Vinyl Ether – toward the Synthesis of a Sterically Locked Phytochrome Chromophore
  作者：Yutaka Ukaji、Ryo Sakata、Takahiro Soeta

  DOI：10.3987/com-14-13157

  日期：——

  Mild hydrolysis of vinyl ether derived from a pyrrole carboxaldehyde corresponding to the B,C-ring component of phytochromobilin chromophore was achieved by treatment with oxalyl chloride in chloroform in the presence of water and ethanol to afford a one-carbon homologated aldehyde. This aldehyde was applied to the synthesis of the sterically locked 15E-anti CD-ring component of the chromophore. Furthermore, the aldehyde could be converted to the intermediate for the sterically locked 5Z-anti AB-ring component.