(1R,3S)-1-(Benzyloxycarbonylamino-methyl)-2-formyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester | 880263-00-3

• 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: (1R,3S)-1-(Benzyloxycarbonylamino-methyl)-2-formyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester
• CAS: 880263-00-3
• 化学式: C₂₃H₂₆N₂O₇
• 分子量: 442.469
• InChiKey: SZXHEQWJLDNISX-OALUTQOASA-N

物化性质

• 沸点：
  639.1±55.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  103.4
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1R,3S)-1-(Benzyloxycarbonylamino-methyl)-2-formyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester 在 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 甲酸 、 草酰氯 、 氢溴酸 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 溶剂黄146 、 二甲基亚砜 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 N-(((6S,9R,14aS,15R)-2,3,11,12-tetramethoxy-16-methyl-7-oxo-6,7,9,14,14a,15-hexahydro-5H-6,15-epiminobenzo[4,5]azocino[1,2-b]isoquinolin-9-yl)methyl)benzamide
  参考文献：
  名称：

  Synthesis and antitumor activity of simplified ecteinascidin–saframycin analogs

  摘要：

  Two series of simplified analogs of the ecteinascidin-saframycin type alkaloids were prepared from L-DOPA. Their in vitro antitumor activity was tested against three human cancer cell lines (HCT-8 colon carcinoma, Bel-7402 liver carcinoma, and BGC-823 gastric carcinoma). Among these compounds, the ester analogs have stronger activities than those of amide analogs in general. Among them, 1-naphthalene carboxylate ester analog 31 has the strongest activity against BGC-823 cells. F (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.069
• 作为产物：
  描述：

  N-(2-氧代乙基)氨基甲酸苄酯 在 sodium acetate 、 乙酸酐 、 potassium carbonate 作用下， 以 溶剂黄146 、 丙酮 为溶剂， 反应 24.0h， 生成 (1R,3S)-1-(Benzyloxycarbonylamino-methyl)-2-formyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and antitumor activity of simplified ecteinascidin–saframycin analogs

  摘要：

  Two series of simplified analogs of the ecteinascidin-saframycin type alkaloids were prepared from L-DOPA. Their in vitro antitumor activity was tested against three human cancer cell lines (HCT-8 colon carcinoma, Bel-7402 liver carcinoma, and BGC-823 gastric carcinoma). Among these compounds, the ester analogs have stronger activities than those of amide analogs in general. Among them, 1-naphthalene carboxylate ester analog 31 has the strongest activity against BGC-823 cells. F (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.069