6-benzyloxy-1-ethoxycarbonylmethyl-7-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester | 918896-62-5

• 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: 6-benzyloxy-1-ethoxycarbonylmethyl-7-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 1-(2-ethoxy-2-oxoethyl)-7-methoxy-6-phenylmethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 918896-62-5
• 化学式: C₂₆H₃₃NO₆
• 分子量: 455.551
• InChiKey: MJXGKPQHRUXWQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-benzyloxy-1-ethoxycarbonylmethyl-7-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 在 咪唑 、 sodium tetrahydroborate 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 6-benzyloxy-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthetic studies on Ecteinascidin-743: synthesis of building blocks through Sharpless asymmetric dihydroxylation and aza-Michael reactions

  摘要：

  A practical and an efficient synthesis of three building blocks of tetrahydroisoquinoline alkaloid Ecteinascidin-743 was accomplished, starting from readily available piperonal, 2-methyl anisole, and veratraldehyde. A combination of Vilsmeier-Haack reaction and Sharpless asymmetric dihydroxylation was employed for the synthesis of building blocks A and B whereas a Heck reaction in PEG-2000 and aza-Michael reactions were employed for the synthesis of building block C. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.056
• 作为产物：
  描述：

  2-溴-5-羟基-4-甲氧基苯甲醛 在 palladium diacetate 乙酸铵 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 sodium carbonate 、 potassium carbonate 、 乙二醇 、 溶剂黄146 、 三乙胺 、 三氟乙酸 、 poly(ethylene glycol) 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 48.0h， 生成 6-benzyloxy-1-ethoxycarbonylmethyl-7-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthetic studies on Ecteinascidin-743: synthesis of building blocks through Sharpless asymmetric dihydroxylation and aza-Michael reactions

  摘要：

  A practical and an efficient synthesis of three building blocks of tetrahydroisoquinoline alkaloid Ecteinascidin-743 was accomplished, starting from readily available piperonal, 2-methyl anisole, and veratraldehyde. A combination of Vilsmeier-Haack reaction and Sharpless asymmetric dihydroxylation was employed for the synthesis of building blocks A and B whereas a Heck reaction in PEG-2000 and aza-Michael reactions were employed for the synthesis of building block C. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.056

文献信息

• Synthetic studies on Ecteinascidin-743: synthesis of building blocks through Sharpless asymmetric dihydroxylation and aza-Michael reactions
  作者：S. Chandrasekhar、N. Ramakrishna Reddy、Y. Srinivasa Rao

  DOI：10.1016/j.tet.2006.09.056

  日期：2006.12

  A practical and an efficient synthesis of three building blocks of tetrahydroisoquinoline alkaloid Ecteinascidin-743 was accomplished, starting from readily available piperonal, 2-methyl anisole, and veratraldehyde. A combination of Vilsmeier-Haack reaction and Sharpless asymmetric dihydroxylation was employed for the synthesis of building blocks A and B whereas a Heck reaction in PEG-2000 and aza-Michael reactions were employed for the synthesis of building block C. (c) 2006 Elsevier Ltd. All rights reserved.