(1R*,6R*,11aS*)-6-benzyloxymethyl-2-tert-butyloxycarbonyl-1,7,8,10-tetramethoxy-9-methyl-1,2,3,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinolin-4-one

• 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*,6R*,11aS*)-6-benzyloxymethyl-2-tert-butyloxycarbonyl-1,7,8,10-tetramethoxy-9-methyl-1,2,3,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinolin-4-one
• 英文别名: tert-butyl (1R,6R,11aS)-1,7,8,10-tetramethoxy-9-methyl-4-oxo-6-(phenylmethoxymethyl)-3,6,11,11a-tetrahydro-1H-pyrazino[1,2-b]isoquinoline-2-carboxylate
• 化学式: C₃₀H₄₀N₂O₈
• 分子量: 556.656
• InChiKey: WLHRYIRZNRLUDA-RXYILKCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1R*,6R*,11aS*)-6-benzyloxymethyl-2-tert-butyloxycarbonyl-1,7,8,10-tetramethoxy-9-methyl-1,2,3,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinolin-4-one 、 3,4-二甲氧基苄氯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.16h， 以68%的产率得到(1R*,3R*,6R*,11aS*)-6-benzyloxymethyl-2-tert-butyloxycarbonyl-1,7,8,10-tetramethoxy-3-(3,4-dimethoxybenzyl)-9-methyl-1,2,3,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinolin-4-one
  参考文献：
  名称：

  C(3)-alkylation and cyclization of pyrazino[1,2-b]isoquinolin-4-ones

  摘要：

  To avoid the epimerization of the C(11a)-stereocenter previously observed in 6,11a-cis-pyrazino[1,2-b]isoquinolin-1,4-diones, we present in this paper the C(3)-alkylation of 1-methoxy-pyrazino[1,2-b]isoquinolin-4-ones to obtain all-cis derivatives through a very reliable protocol. The success of the acid-promoted cyclization to get pentacyclic (R-3=arylmethyl) or tetracyclic (R-3=2-bromo-2-propenyl) compounds is dependent on the nature of the C(3)-unsaturated chain and of the N-substituent, but these limitations have been overcome by using trifluoromethanesulfonic as a superacid catalyst. The C-(3)-alkylation of pyrazinol 1,2-b]isoquinolin-4-one is also Studied. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.016
• 作为产物：
  描述：

  甲醇 、 (1RS,6RS,11aSR)-6-benzyloxymethyl-1-hydroxy-2-(tert-butyloxycarbonyl)-7,8,10-trimethoxy-9-methyl-1,2,3,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinolin-4-one 在 4-甲基苯磺酸吡啶 作用下， 反应 48.0h， 以3.3 g的产率得到(1R*,6R*,11aS*)-6-benzyloxymethyl-2-tert-butyloxycarbonyl-1,7,8,10-tetramethoxy-9-methyl-1,2,3,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinolin-4-one
  参考文献：
  名称：

  C(3)-alkylation and cyclization of pyrazino[1,2-b]isoquinolin-4-ones

  摘要：

  To avoid the epimerization of the C(11a)-stereocenter previously observed in 6,11a-cis-pyrazino[1,2-b]isoquinolin-1,4-diones, we present in this paper the C(3)-alkylation of 1-methoxy-pyrazino[1,2-b]isoquinolin-4-ones to obtain all-cis derivatives through a very reliable protocol. The success of the acid-promoted cyclization to get pentacyclic (R-3=arylmethyl) or tetracyclic (R-3=2-bromo-2-propenyl) compounds is dependent on the nature of the C(3)-unsaturated chain and of the N-substituent, but these limitations have been overcome by using trifluoromethanesulfonic as a superacid catalyst. The C-(3)-alkylation of pyrazinol 1,2-b]isoquinolin-4-one is also Studied. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.016

文献信息

• C(3)-alkylation and cyclization of pyrazino[1,2-b]isoquinolin-4-ones
  作者：Irene Ortín、Juan Francisco González、Elena de la Cuesta、Carmen Avendaño

  DOI：10.1016/j.tet.2009.10.016

  日期：2009.11

  To avoid the epimerization of the C(11a)-stereocenter previously observed in 6,11a-cis-pyrazino[1,2-b]isoquinolin-1,4-diones, we present in this paper the C(3)-alkylation of 1-methoxy-pyrazino[1,2-b]isoquinolin-4-ones to obtain all-cis derivatives through a very reliable protocol. The success of the acid-promoted cyclization to get pentacyclic (R-3=arylmethyl) or tetracyclic (R-3=2-bromo-2-propenyl) compounds is dependent on the nature of the C(3)-unsaturated chain and of the N-substituent, but these limitations have been overcome by using trifluoromethanesulfonic as a superacid catalyst. The C-(3)-alkylation of pyrazinol 1,2-b]isoquinolin-4-one is also Studied. (C) 2009 Elsevier Ltd. All rights reserved.