2-[2-[(1R)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]ethyl]isoindole-1,3-dione | 1448550-18-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 2-[2-[(1R)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]ethyl]isoindole-1,3-dione
• CAS: 1448550-18-2
• 化学式: C₂₁H₁₉N₃O₂
• 分子量: 345.401
• InChiKey: KRZDKVKHFSIWIZ-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  65.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[2-[(1R)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]ethyl]isoindole-1,3-dione 在 4-二甲氨基吡啶 、 肼 作用下， 以 二氯甲烷 为溶剂， 生成 ditert-butyl (1R)-1-(2-aminoethyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2,9-dicarboxylate
  参考文献：
  名称：

  First Total Synthesis and Absolute Configuration of Keramamine C

  摘要：

  Asymmetric first total synthesis of keramamine C, a tetrahydro-beta-carboline alkaloid from an Okinawan marine sponge Amphimedon sp., has been accomplished with the Bischler-Napieralski reaction and the Noyori catalytic asymmetric hydrogen-transfer reaction. The absolute configuration of keramamine C was elucidated to be 1R from comparison of the H-1 and C-13 NMR, CD spectral data and [alpha](D), values of synthetic and natural keramamine C, respectively.

  DOI：

  10.3987/com-12-s(n)123
• 作为产物：
  描述：

  2-[2-(4,9-dihydro-3H-pyrido[3,4-b]indol-1-yl)ethyl]isoindole-1,3-dione 在 甲酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以89%的产率得到2-[2-[(1R)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]ethyl]isoindole-1,3-dione
  参考文献：
  名称：

  First Total Synthesis and Absolute Configuration of Keramamine C

  摘要：

  Asymmetric first total synthesis of keramamine C, a tetrahydro-beta-carboline alkaloid from an Okinawan marine sponge Amphimedon sp., has been accomplished with the Bischler-Napieralski reaction and the Noyori catalytic asymmetric hydrogen-transfer reaction. The absolute configuration of keramamine C was elucidated to be 1R from comparison of the H-1 and C-13 NMR, CD spectral data and [alpha](D), values of synthetic and natural keramamine C, respectively.

  DOI：

  10.3987/com-12-s(n)123

文献信息

• First Total Synthesis and Absolute Configuration of Keramamine C
  作者：Jun'ichi Kobayashi、Haruaki Ishiyama、Yuta Mori、Takashi Matsumoto

  DOI：10.3987/com-12-s(n)123

  日期：——

  Asymmetric first total synthesis of keramamine C, a tetrahydro-beta-carboline alkaloid from an Okinawan marine sponge Amphimedon sp., has been accomplished with the Bischler-Napieralski reaction and the Noyori catalytic asymmetric hydrogen-transfer reaction. The absolute configuration of keramamine C was elucidated to be 1R from comparison of the H-1 and C-13 NMR, CD spectral data and [alpha](D), values of synthetic and natural keramamine C, respectively.