diisopropyl (S)-(-)-N-<(2,3,5-trimethoxy-4-methylphenyl)methyl>-α-aminoadipate | 143724-52-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diisopropyl (S)-(-)-N-<(2,3,5-trimethoxy-4-methylphenyl)methyl>-α-aminoadipate
• CAS: 143724-52-1
• 化学式: C₂₃H₃₇NO₇
• 分子量: 439.549
• InChiKey: ZDCOQNVUEZKUIF-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  31.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  92.32
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  diisopropyl (S)-(-)-N-<(2,3,5-trimethoxy-4-methylphenyl)methyl>-α-aminoadipate 在 三乙基硅烷 、 氢氧化钾 、 sodium tetrahydroborate 、 硝酸 、 四氯化锡 、 溶剂黄146 、 三氟乙酸 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 13.0h， 生成 (+/-)-8-methoxy-9-methyl-1,3,4,6,11,11a-hexahydro-2H-benzoquinolizine-4,7,10-trione
  参考文献：
  名称：

  A Synthesis of 4-Cyano-hexahydro-2H-benzo[b]quinolizine-7,10-dione as a Simple Model Compound of Saframycin A

  摘要：

  A simple and efficient synthesis of 4-cyano-8-methoxy-9-methyl-1,3,4,6,11,11a-hexahydro-2H-benzo[b]quinolizine-7,10-dione (20a) as a simple model compound of saframycin A (1) is described starting from the corresponding lactam (16). Reduction of the lactam (16) with lithium aluminum hydride followed by sodium cyanide treatment afforded the alpha-amino nitrile (19) as an inseparable mixture in an excellent yield. Oxidative demethylation of compound (19) with 1ON HNO3 gave the title compound (20a) and its C-4 epimer (20b). The structure of 20a was confirmed by H-1 nmr and C-13 nmr spectroscopic analysis.

  DOI：

  10.3987/com-92-6017
• 作为产物：
  描述：

  diisopropyl (S)-α-aminoadipate 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 39.0h， 生成 diisopropyl (S)-(-)-N-<(2,3,5-trimethoxy-4-methylphenyl)methyl>-α-aminoadipate
  参考文献：
  名称：

  A Synthesis of 4-Cyano-hexahydro-2H-benzo[b]quinolizine-7,10-dione as a Simple Model Compound of Saframycin A

  摘要：

  A simple and efficient synthesis of 4-cyano-8-methoxy-9-methyl-1,3,4,6,11,11a-hexahydro-2H-benzo[b]quinolizine-7,10-dione (20a) as a simple model compound of saframycin A (1) is described starting from the corresponding lactam (16). Reduction of the lactam (16) with lithium aluminum hydride followed by sodium cyanide treatment afforded the alpha-amino nitrile (19) as an inseparable mixture in an excellent yield. Oxidative demethylation of compound (19) with 1ON HNO3 gave the title compound (20a) and its C-4 epimer (20b). The structure of 20a was confirmed by H-1 nmr and C-13 nmr spectroscopic analysis.

  DOI：

  10.3987/com-92-6017

文献信息

• A Synthesis of 4-Cyano-hexahydro-2H-benzo[b]quinolizine-7,10-dione as a Simple Model Compound of Saframycin A
  作者：Akinori Kubo、Tatsuya Nakai、Yuichi Koizumi、Naoki Saito、Yuzuru Mikami、Katsukiyo Yazawa、Jun Uno

  DOI：10.3987/com-92-6017

  日期：——

  A simple and efficient synthesis of 4-cyano-8-methoxy-9-methyl-1,3,4,6,11,11a-hexahydro-2H-benzo[b]quinolizine-7,10-dione (20a) as a simple model compound of saframycin A (1) is described starting from the corresponding lactam (16). Reduction of the lactam (16) with lithium aluminum hydride followed by sodium cyanide treatment afforded the alpha-amino nitrile (19) as an inseparable mixture in an excellent yield. Oxidative demethylation of compound (19) with 1ON HNO3 gave the title compound (20a) and its C-4 epimer (20b). The structure of 20a was confirmed by H-1 nmr and C-13 nmr spectroscopic analysis.