(1R,10R,13S)-19-hydroxy-5,7,16,18-tetramethoxy-6,17,21-trimethyl-8-phenylmethoxy-10-(phenylmethoxymethyl)-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-2,4(9),5,7,15(20),16,18-heptaen-12-one | 935268-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (1R,10R,13S)-19-hydroxy-5,7,16,18-tetramethoxy-6,17,21-trimethyl-8-phenylmethoxy-10-(phenylmethoxymethyl)-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-2,4(9),5,7,15(20),16,18-heptaen-12-one
• CAS: 935268-12-5
• 化学式: C₄₁H₄₄N₂O₈
• 分子量: 692.809
• InChiKey: MMRQQRXOUAVSPL-JHFJJOSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  51
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1R,10R,13S)-19-hydroxy-5,7,16,18-tetramethoxy-6,17,21-trimethyl-8-phenylmethoxy-10-(phenylmethoxymethyl)-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-2,4(9),5,7,15(20),16,18-heptaen-12-one 在 palladium dichloride 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 15.0h， 以99%的产率得到(1R,10R,13S)-8,19-dihydroxy-10-(hydroxymethyl)-5,7,16,18-tetramethoxy-6,17,21-trimethyl-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-2,4(9),5,7,15(20),16,18-heptaen-12-one
  参考文献：
  名称：

  （-）-cribrostatin 4（renieramycin H）的不对称全合成。

  摘要：

  DOI：

  10.1002/anie.200604126
• 作为产物：
  描述：

  (2aS,4R,8bR)-1-benzyl-3-[(2S)-3-(5-hydroxy-2,4-dimethoxy-3-methylphenyl)-2-(methylamino)propanoyl]-6,8-dimethoxy-7-methyl-5-phenylmethoxy-4-(phenylmethoxymethyl)-4,8b-dihydro-2aH-azeto[3,2-c]isoquinolin-2-one 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以62%的产率得到(1R,10R,13S)-19-hydroxy-5,7,16,18-tetramethoxy-6,17,21-trimethyl-8-phenylmethoxy-10-(phenylmethoxymethyl)-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-2,4(9),5,7,15(20),16,18-heptaen-12-one
  参考文献：
  名称：

  （-）-cribrostatin 4（renieramycin H）的不对称全合成。

  摘要：

  DOI：

  10.1002/anie.200604126

文献信息

• Regioselectivity of Pictet–Spengler cyclization reactions to construct the pentacyclic frameworks of the ecteinascidin–saframycin class of tetrahydroisoquinoline antitumor antibiotics
  作者：Guillaume Vincent、Jonathan W. Lane、Robert M. Williams

  DOI：10.1016/j.tetlet.2007.03.113

  日期：2007.5

  The regiochemical outcome of Pictet-Spengler cyclization reactions directed toward the preparation of the pentacyclic core of the ecteinascidin class of antitumor antibiotics has been investigated on two different phenolic substrates. In one substrate, the assistance of an incipient benzylamine group at C-4 is postulated to direct the cyclization in favor of the pentacyclic framework of ET-743, which bears a hydroxyl group at C-18. Conversely, cyclization of an alternative substrate lacking a heteroatom at C-4 favors the opposite regiochemical outcome, primarily affording an unnatural pentacyclic core bearing a hydroxyl group at C-16. (c) 2007 Elsevier Ltd. All rights reserved.