tert-butyl (E)-3-(3-(allyloxy)-3-oxopropyl)-5-(1-(4-ethyl-3-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)pentyl)-4-methyl-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 (E)-3-(3-(allyloxy)-3-oxopropyl)-5-(1-(4-ethyl-3-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)pentyl)-4-methyl-1H-pyrrole-2-carboxylate
• 英文别名: tert-butyl 5-[(1E)-1-(4-ethyl-3-methyl-5-oxopyrrol-2-ylidene)pentyl]-4-methyl-3-(3-oxo-3-prop-2-enoxypropyl)-1H-pyrrole-2-carboxylate
• 化学式: C₂₈H₄₀N₂O₅
• 分子量: 484.636
• InChiKey: DJGMMRWLVMQRLI-DARPEHSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  97.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  t-butyl 3-(3-allyloxy-3-oxopropyl)-5-[(4-ethyl-3-methyl-5-oxo-1H-pyrrol-2(5H)-ylidene)methyl]-4-methyl-1H-pyrrole-2-carboxylate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 tert-butyl (E)-3-(3-(allyloxy)-3-oxopropyl)-5-(1-(4-ethyl-3-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)pentyl)-4-methyl-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Regioselective Introduction of Substituents to the meso-Position of Pyrromethenone Derivative – Application to the Synthesis of Sterically Fixed Phytochrome Chromophore Anchored to the C15 meso-Position

  摘要：

  Pyrromethenone derivatives corresponding to the CD-ring component of phycocyanobilin chromophore were regioselectively brominated with NBS at the meso-position retaining the stereochemistry of the olefinic carbon skeleton. Subsequent introduction of carbon-substituents to the brominated pyrromethenones was accomplished by treating with Grignard reagents to afford meso-alkylated (E)-isomers regardless of the stereochemistry of the starting brominated pyrromethenones. The resulting product was applied to the synthesis of a meso-anchored sterically fixed tetrapyrrole chromophore.

  DOI：

  10.3987/com-14-s(k)97

文献信息

• Synthesis of Sterically Fixed Phytochrome Chromophore Derivatives Bearing a 15<i>E</i>-<i>Fixed</i> or 15<i>E</i>-<i>Anti</i>-<i>Fixed</i> CD-Ring Component
  作者：Takahiro Soeta、Nobuhiko Ohashi、Toshiharu Kobayashi、Yoko Sakata、Takuya Suga、Yutaka Ukaji

  DOI：10.1021/acs.joc.8b01252

  日期：2018.9.21

  To analyze the structure and function of phytochrome chromophores, we have been synthesizing natural and unnatural bilin chromophores of phytochromes. In this manuscript, we report the synthesis of sterically fixed 15E-fixed 18Et-biliverdin (BV) and 15E-anti-fixed 18Et-BV derivatives. The key reaction is the introduction of an sp(3) carbon alkyl chain bearing a leaving group at the meso-position of the CD-ring component by using the corresponding Grignard reagents in the presence of LiCl.
• Regioselective Introduction of Substituents to the meso-Position of Pyrromethenone Derivative – Application to the Synthesis of Sterically Fixed Phytochrome Chromophore Anchored to the C15 meso-Position
  作者：Yutaka Ukaji、Yudai Tanaka、Ryoji Iwamoto、Ryo Sakata、Takahiro Soeta、Kohei Endo、Shuhei Fujinami、Katsuhiko Inomata

  DOI：10.3987/com-14-s(k)97

  日期：——

  Pyrromethenone derivatives corresponding to the CD-ring component of phycocyanobilin chromophore were regioselectively brominated with NBS at the meso-position retaining the stereochemistry of the olefinic carbon skeleton. Subsequent introduction of carbon-substituents to the brominated pyrromethenones was accomplished by treating with Grignard reagents to afford meso-alkylated (E)-isomers regardless of the stereochemistry of the starting brominated pyrromethenones. The resulting product was applied to the synthesis of a meso-anchored sterically fixed tetrapyrrole chromophore.