methyl 4-(3,6-dihydro-2H-pyran-4-yl)-2-isopropyl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-3-carboxylate | 1610785-57-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-(3,6-dihydro-2H-pyran-4-yl)-2-isopropyl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-3-carboxylate
• 英文别名: Methyl 4-(3,6-dihydro-2H-pyran-4-yl)-5,6,7,8-tetrahydro-7,7-dimethyl-2-(1-methylethyl)-5-oxo-3-quinolinecarboxylate；methyl 4-(3,6-dihydro-2H-pyran-4-yl)-7,7-dimethyl-5-oxo-2-propan-2-yl-6,8-dihydroquinoline-3-carboxylate
• CAS: 1610785-57-3
• 化学式: C₂₁H₂₇NO₄
• 分子量: 357.45
• InChiKey: JGGKXQMALNSQAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-(3,6-dihydro-2H-pyran-4-yl)-2-isopropyl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-3-carboxylate 在 三氟甲磺酸 作用下， 以77.3%的产率得到4-isopropyl-7,7-dimethyl-2',3',5',6',7,8-hexahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-3,9(6H)-dione
  参考文献：
  名称：

  高效进入多环胆固醇酯转移蛋白抑制剂的实用对映选择性合成方法。

  摘要：

  已经开发了手性多环胆固醇酯转移蛋白（CETP）抑制剂1的有效对映选择性合成。通过开发改良的Hantzsch型反应以制备位阻吡啶环，利用新型BIBOP-氨基吡啶衍生的Ru配合物对位酮6进行对映选择性氢化，有效的ICl促进内酯形成，以及通过合成IHC促进内酯的形成，使该合成大规模可行。BF 3介导的氢化过程，用于非对映选择性的乳糖醇还原。这种有效的途径已成功扩展规模，以产生具有挑战性的CETP候选药物1的多千克数量。

  DOI：

  10.1021/ol501833g
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 在 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 醋酸异丙酯 为溶剂， 反应 13.67h， 生成 methyl 4-(3,6-dihydro-2H-pyran-4-yl)-2-isopropyl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-3-carboxylate
  参考文献：
  名称：

  [EN] NOVEL RUTHENIUM CATALYSTS AND THEIR USE FOR ASYMMETRIC REDUCTION OF KETONES
  [FR] NOUVEAUX CATALYSEURS AU RUTHÉNIUM ET LEUR UTILISATION POUR LA RÉDUCTION ASYMÉTRIQUE DE CÉTONES

  摘要：

  揭示了一种新型钌化合物的结构式(Ia)和(Ib)：其中R1和基团L ∩ L在此定义。还揭示了一种使用这些新型钌化合物作为催化剂进行不对称加氢和酮的转移加氢的方法，具有高反应性和优异选择性。

  公开号：

  WO2015002769A1

文献信息

• METHOD FOR THE PREPARATION OF (4S)-4-(4-CYANO-2-METHOXYPHENYL)-5-ETHOXY-2,8-DIMETHYL-1,4-DIHYDRO-1-6-NAPHTHYRIDINE-3-CARBOXAMIDE AND RECOVERY OF (4S)-4-(4-CYANO-2-METHOXYPHENYL)-5-ETHOXY-2,8-DIMETHYL-1,4-DIHYDRO-1-6-NAPHTHYRIDINE-3-CARBOXAMIDE BY ELECTROCHEMICAL METHODS
  申请人：Bayer Pharma Aktiengesellschaft

  公开号：US20180244668A1

  公开（公告）日：2018-08-30

  The present invention relates to a novel process for preparing (4S)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide of the formula (I) and recovering (4S)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide of the formula (I) proceeding from (4R)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide of the formula ent-(I)

  本发明涉及一种制备（4S）-4-(4-氰基-2-甲氧基苯基)-5-乙氧基-2,8-二甲基-1,4-二氢-1,6-萘啶-3-羧酰胺（式(I)）并从（4R）-4-(4-氰基-2-甲氧基苯基)-5-乙氧基-2,8-二甲基-1,4-二氢-1,6-萘啶-3-羧酰胺ent-(I)的方法中回收（4S）-4-(4-氰基-2-甲氧基苯基)-5-乙氧基-2,8-二甲基-1,4-二氢-1,6-萘啶-3-羧酰胺（式(I)）的新工艺。
• NOVEL RUTHENIUM CATALYSTS AND THEIR USE FOR ASYMMETRIC REDUCTION OF KETONES
  申请人：HADDAD Nizar

  公开号：US20150005500A1

  公开（公告）日：2015-01-01

  Disclosed are novel ruthenium compounds of formula (Ia) and (Ib): wherein R 1 and the moiety are defined herein. Also disclosed is a process for using these novel ruthenium compounds as catalysts for asymmetric hydrogenation and transfer hydrogenation of ketones with high reactivities and excellent selectivities.

  本发明揭示了一种新型钌化合物的化学式(Ia)和(Ib)：其中R1和该基团在此定义。还揭示了一种使用这些新型钌化合物作为催化剂进行酮类的不对称氢化和转移氢化的方法，具有高反应性和优异选择性。
• Method for the preparation of (4S)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1-6-naphthyridine-3-carboxamide and recovery of (4S)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1-6-naphthyridine-3-carboxamide by electrochemical methods
  申请人：Bayer Pharma Aktiengesellschaft

  公开号：US10392384B2

  公开（公告）日：2019-08-27

  The present invention relates to a novel process for preparing (4S)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide of the formula (I) and recovering (4S)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide of the formula (I) proceeding from (4R)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide of the formula ent-(I)

  本发明涉及一种制备式(I)的(4S)-4-(4-氰基-2-甲氧基苯基)-5-乙氧基-2,8-二甲基-1,4-二氢-1,6-萘啶-3-甲酰胺和回收式(I)的(4S)-4-(4-氰基-2-甲氧基苯基)-5-乙氧基-2,8-二甲基-1,4-二氢-1,6-萘啶-3-甲酰胺的新工艺 由式 ent-(I)的(4R)-4-(4-氰基-2-甲氧基苯基)-5-乙氧基-2,8-二甲基-1,4-二氢-1,6-萘啶-3-甲酰胺得到
• Amine-Tunable Ruthenium Catalysts for Asymmetric Reduction of Ketones
  作者：Sonia Rodríguez、Bo Qu、Keith R. Fandrick、Frederic Buono、Nizar Haddad、Yibo Xu、Melissa A. Herbage、Xingzhong Zeng、Shengli Ma、Nelu Grinberg、Heewon Lee、Zhengxu S. Han、Nathan K. Yee、Chris H. Senanayake

  DOI：10.1002/adsc.201300727

  日期：2014.2.10

  AbstractA series of efficient ruthenium catalysts has been developed for the asymmetric hydrogenation and transfer hydrogenation of ketones with high reactivities and selectivities. The new chiral bisdihydrobenzooxaphosphole (BIBOP)/diamine‐ruthenium complexes catalyzed the enantioselective hydrogenation of substrates such as aryl and heteroaryl cyclic and alkyl ketones with substrate/catalyst (S/C) ratios of up to 100,000. The opposite sense of enantioselectivity can be obtained by proper selection of a diamine with a given chirality of the phosphine. The usefulness of the new system has been demonstrated in the asymmetric hydrogenation of a complex synthetic intermediate towards cholesteryl ester transfer protein (CETP) inhibitors at S/C 20,000 on large‐scale operation.magnified image
• VERFAHREN ZUR HERSTELLUNG VON (4S)-4-(4-CYANO-2-METHOXYPHENYL)-5-ETHOXY-2,8-DIMETHYL-1,4-DIHYDRO-1,6-NAPHTHYRIDIN-3-CARBOXAMID UND WIEDERGEWINNUNG VON (4S)-4-(4-CYANO-2-METHOXYPHENYL)-5-ETHOXY-2,8-DIMETHYL-1,4-DIHYDRO-1,6-NAPHTHYRIDIN-3-CARBOXAMID MITTELS ELEKTROCHEMISCHER METHODEN
  申请人：Bayer Pharma Aktiengesellschaft

  公开号：EP3337801A1

  公开（公告）日：2018-06-27