benzyl (3R)-3-(2,3-dihydro-1-benzofuran-6-yl)-2,7-dioxo-1,2,3,5,6,7-hexahydro-4H-1,4-benzodiazonine-4-carboxylate | 908371-49-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (3R)-3-(2,3-dihydro-1-benzofuran-6-yl)-2,7-dioxo-1,2,3,5,6,7-hexahydro-4H-1,4-benzodiazonine-4-carboxylate
• 英文别名: (3R)-3-(2,3-dihydro-benzofuran-5-yl)-2,7-dioxo-1,2,3,5,6,7-hexahydro-benzo[e][1,4]diazonine-4-carboxylic acid benzyl ester；benzyl (3R)-3-(2,3-dihydro-1-benzofuran-5-yl)-2,7-dioxo-1,3,5,6-tetrahydro-1,4-benzodiazonine-4-carboxylate
• CAS: 908371-49-3
• 化学式: C₂₇H₂₄N₂O₅
• 分子量: 456.498
• InChiKey: IANYJFCMPITHNX-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (3R)-3-(2,3-dihydro-1-benzofuran-6-yl)-2,7-dioxo-1,2,3,5,6,7-hexahydro-4H-1,4-benzodiazonine-4-carboxylate 在 palladium on activated charcoal 、 氢气 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 (R)-(-)-1,2,3,4-tetrahydro-3-(2,3-dihydrobenzofuran-5-yl)-9H-pyrrolo-[3,4-b]quinolin-9-one
  参考文献：
  名称：

  Development of a Scalable and Safe Procedure for the Production of (3R)-3-(2,3-Dihydro-1-benzofuran-5-yl)-1,2,3,4-tetrahydro-9H-pyrrolo[3,4-b]- quinolin-9-one, an Intermediate in the Synthesis of PDE-V Inhibitors RWJ387273 (R301249) and RWJ444772 (R290629)

  摘要：

  A scalable and safe process for the oxidative rearrangement of beta-carboline to quinolone derivatives, intermediates in the synthesis of PDE-V inhibitors RWJ387273 (R301249) and RWJ444772 (R290629), has been developed.

  DOI：

  10.1021/op060099f
• 作为产物：
  描述：

  1-(R)-1-(2,3-dihydrobenzofuran-5-yl)-2,3,4,9-tetrahydro-1H-β-carboline 在 Oxone 、 碳酸氢钠 、 三乙胺 、 丙酮 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 7.75h， 生成 benzyl (3R)-3-(2,3-dihydro-1-benzofuran-6-yl)-2,7-dioxo-1,2,3,5,6,7-hexahydro-4H-1,4-benzodiazonine-4-carboxylate
  参考文献：
  名称：

  Development of a Scalable and Safe Procedure for the Production of (3R)-3-(2,3-Dihydro-1-benzofuran-5-yl)-1,2,3,4-tetrahydro-9H-pyrrolo[3,4-b]- quinolin-9-one, an Intermediate in the Synthesis of PDE-V Inhibitors RWJ387273 (R301249) and RWJ444772 (R290629)

  摘要：

  A scalable and safe process for the oxidative rearrangement of beta-carboline to quinolone derivatives, intermediates in the synthesis of PDE-V inhibitors RWJ387273 (R301249) and RWJ444772 (R290629), has been developed.

  DOI：

  10.1021/op060099f

文献信息

• ENANTIOSELECTIVE SYNTHESIS OF ASYMMETRIC BETA-CARBOLINE INTERMEDIATES
  申请人：Santos Leonardo

  公开号：US20110245503A1

  公开（公告）日：2011-10-06

  Described herein is a new asymmetric synthesis of imines to obtain β-carboline derivatives useful as key intermediate compounds for the synthesis of phosphodiesterase inhibitors using a new process with palladium or ruthenium hydride and/or nickel boride to reduce chiral intermediates. The use of chloroformate chiral auxiliaries is further described for the reduction and asymmetric hydrogenation of imines to obtain β-carboline derivatives and intermediate compounds used in the preparation thereof.

  本文介绍了一种新的不对称合成亚胺的方法，以获得β-咔啉衍生物，这些衍生物是合成磷酸二酯酶抑制剂的关键中间体化合物。该方法使用钯或钌氢化物和/或镍硼化物来还原手性中间体。进一步描述了氯甲酸酯手性辅助剂的使用，用于还原和不对称氢化亚胺，以获得β-咔啉衍生物和用于制备它们的中间体化合物。
• Efficient and stereoselective process for large scale synthesis of (3R)-3-(2,3-dihydrobenzofuran-5-yl)-1,2,3,4-tetrahydropyrrolo[3,4-b]quinolin-9-one derivatives
  申请人：Li Xun

  公开号：US20070015798A1

  公开（公告）日：2007-01-18

  This invention relates to an efficient process for large scale stereoselective production of (3R)-3-(2,3-dihydrobenzofuran-5-yl)-1,2,3,4-tetrahydropyrrolo[3,4-b]quinolin-9-ones and key intermediates used for the preparation of benzofuranyl pyrroloquinolones as potent and selective PDE5 inhibitors for the treatment of erectile dysfunction, as well as pharmaceutical compositions and methods of treatment utilizing these compounds.

  本发明涉及一种有效的大规模立体选择性生产(3R)-3-(2,3-二氢苯并呋喃-5-基)-1,2,3,4-四氢吡咯并[3,4-b]喹啉-9-酮及其在制备苯并呋喃基吡咯喹啉类PDE5抑制剂用作治疗勃起功能障碍的关键中间体方面的应用，以及利用这些化合物的制药组合物和治疗方法。
• WO2006/93719
  申请人：——

  公开号：——

  公开（公告）日：——
• Development of a Scalable and Safe Procedure for the Production of (3<i>R</i>)-3-(2,3-Dihydro-1-benzofuran-5-yl)-1,2,3,4-tetrahydro-9<i>H</i>-pyrrolo[3,4-<i>b</i>]- quinolin-9-one, an Intermediate in the Synthesis of PDE-V Inhibitors RWJ387273 (R301249) and RWJ444772 (R290629)
  作者：Bert Willemsens、Ivan Vervest、Dominic Ormerod、Wim Aelterman、Christine Fannes、Narda Mertens、István E. Markó、Sebastien Lemaire

  DOI：10.1021/op060099f

  日期：2006.11.1

  A scalable and safe process for the oxidative rearrangement of beta-carboline to quinolone derivatives, intermediates in the synthesis of PDE-V inhibitors RWJ387273 (R301249) and RWJ444772 (R290629), has been developed.