(1R,2R,10R,13S)-19-hydroxy-5,7,18-trimethoxy-6,17,21-trimethyl-8-prop-2-enoxy-10-(prop-2-enoxymethyl)-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-4(9),5,7,15(20),16,18-hexaen-12-one | 942197-87-7

• 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,2R,10R,13S)-19-hydroxy-5,7,18-trimethoxy-6,17,21-trimethyl-8-prop-2-enoxy-10-(prop-2-enoxymethyl)-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-4(9),5,7,15(20),16,18-hexaen-12-one
• CAS: 942197-87-7
• 化学式: C₃₂H₄₀N₂O₇
• 分子量: 564.679
• InChiKey: QGQDVHLMMWCXEV-KSZLKVKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1R,2R,10R,13S)-19-hydroxy-5,7,18-trimethoxy-6,17,21-trimethyl-8-prop-2-enoxy-10-(prop-2-enoxymethyl)-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-4(9),5,7,15(20),16,18-hexaen-12-one 在 potassium dihydrogenphosphate 、 potassium nitrososulfonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以50%的产率得到(1R,2R,10R,13S)-5,7,18-trimethoxy-6,17,21-trimethyl-8-prop-2-enoxy-10-(prop-2-enoxymethyl)-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-4(9),5,7,15(20),17-pentaene-12,16,19-trione
  参考文献：
  名称：

  Regioselectivity of Pictet–Spengler cyclization reactions to construct the pentacyclic frameworks of the ecteinascidin–saframycin class of tetrahydroisoquinoline antitumor antibiotics

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2007.03.113
• 作为产物：
  描述：

  (S)-3-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-phenyl]-2-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-propionic acid 在 2,6-二甲基吡啶 、 甲酸 、 草酰氯 、 四丁基氟化铵 、 二甲基亚砜 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.09h， 生成 (1R,2R,10R,13S)-19-hydroxy-5,7,18-trimethoxy-6,17,21-trimethyl-8-prop-2-enoxy-10-(prop-2-enoxymethyl)-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-4(9),5,7,15(20),16,18-hexaen-12-one
  参考文献：
  名称：

  Regioselectivity of Pictet–Spengler cyclization reactions to construct the pentacyclic frameworks of the ecteinascidin–saframycin class of tetrahydroisoquinoline antitumor antibiotics

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2007.03.113

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.