tert-butyl N-[N-[(2-methylpropan-2-yl)oxycarbonyl]-N'-[3-[(1R)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]propyl]carbamimidoyl]carbamate | 1020411-40-8

• 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: tert-butyl N-[N-[(2-methylpropan-2-yl)oxycarbonyl]-N'-[3-[(1R)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]propyl]carbamimidoyl]carbamate
• CAS: 1020411-40-8
• 化学式: C₂₅H₃₇N₅O₄
• 分子量: 471.6
• InChiKey: DRIGSZDVLAWMGW-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  117
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[N-[(2-methylpropan-2-yl)oxycarbonyl]-N'-[3-[(1R)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]propyl]carbamimidoyl]carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (R)-trypargine
  参考文献：
  名称：

  Enantioselective synthesis of (+)-trypargine and (+)-crispine E

  摘要：

  Asymmetric transfer hydrogenation was used as a key step in the synthesis of two guanidine-derived alkaloids (+)-trypargine and (+)-crispine E. The enantiomeric compositions of key intermediates were established on the basis of H-1 NMR spectra with chiral solvating agents. The absolute stereochemistry was proven by X-ray crystallography. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.088
• 作为产物：
  描述：

  (R)-3-(2,3,4,9-Tetrahydro-1H-β-carbolin-1-yl)-propylamine 、 N,N'-bis-Boc-S-methyl-isothiourea 在 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以897 mg的产率得到tert-butyl N-[N-[(2-methylpropan-2-yl)oxycarbonyl]-N'-[3-[(1R)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]propyl]carbamimidoyl]carbamate
  参考文献：
  名称：

  Enantioselective synthesis of (+)-trypargine and (+)-crispine E

  摘要：

  Asymmetric transfer hydrogenation was used as a key step in the synthesis of two guanidine-derived alkaloids (+)-trypargine and (+)-crispine E. The enantiomeric compositions of key intermediates were established on the basis of H-1 NMR spectra with chiral solvating agents. The absolute stereochemistry was proven by X-ray crystallography. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.088

文献信息

• Enantioselective synthesis of (+)-trypargine and (+)-crispine E
  作者：Stefan J. Czarnocki、Krystyna Wojtasiewicz、Adam P. Jóźwiak、Jan K. Maurin、Zbigniew Czarnocki、Józef Drabowicz

  DOI：10.1016/j.tet.2008.01.088

  日期：2008.3

  Asymmetric transfer hydrogenation was used as a key step in the synthesis of two guanidine-derived alkaloids (+)-trypargine and (+)-crispine E. The enantiomeric compositions of key intermediates were established on the basis of H-1 NMR spectra with chiral solvating agents. The absolute stereochemistry was proven by X-ray crystallography. (c) 2008 Elsevier Ltd. All rights reserved.