ethyl (S)-4-methyl-1,2,3,6-tetrahydropyridine-2-carboxylate hydrochloride | 169949-73-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (S)-4-methyl-1,2,3,6-tetrahydropyridine-2-carboxylate hydrochloride
• 英文别名: 4-Methyl-1,2,3,6-tetrahydropyridine-2(S)-carboxylic acid ethyl ester hydrochloride；ethyl (2S)-4-methyl-1,2,3,6-tetrahydropyridine-2-carboxylate;hydrochloride
• CAS: 169949-73-9
• 化学式: C₉H₁₅NO₂*ClH
• 分子量: 205.685
• InChiKey: GCTSIGJWCXAODO-QRPNPIFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.28
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl (S(S))-4-methyl-1-(p-tolylsulfinyl)-1,2,3,6-tetrahydropyridine-2-carboxylate 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以78%的产率得到ethyl (S)-4-methyl-1,2,3,6-tetrahydropyridine-2-carboxylate hydrochloride
  参考文献：
  名称：

  在立体选择性氮杂-Diels-Alder反应中使用两种旋光性N-亚磺酰基α-亚氨基酯

  摘要：

  非对映选择性氮杂狄尔斯-阿尔德（氮杂-DA）乙基的反应（小号） - ñ - （叔-butanesulfinyl）iminoacetate（图2a）和乙基（小号） - ñ - （p -toluenesulfinyl）iminoacetate（2B）具有不同的二烯包括描述了在路易斯酸存在下的活化，非活化，环状和无环二烯。发现与2a的反应更具选择性。未活化的二烯（无环和环状）与化学计量的TMSOTf作为路易斯酸的反应以适中的收率和高达99％的非对映选择性提供了aza-DA加合物。观察到强烈倾向于重新接近2a。环二烯使exo加合物成为主要产物。对于与活化的Danishefsky型二烯的氮杂-DA反应，观察到较差的非对映选择性。在这些情况下，使用化学计量的BF 3 ·Et 2 O作为路易斯酸可获得最佳结果（最高69％de，76％收率）。通过与已知化合物的化学相关性确定了六种加成产物的绝对构型。在没有

  DOI：

  10.1016/j.tet.2009.01.090

文献信息

• Antithrombotic amidinophenylalanine and amidinopyridylalanine derivatives
  申请人：Pfizer Inc.

  公开号：US05750520A1

  公开（公告）日：1998-05-12

  This invention relates to compounds of formula (I), ##STR1## pharmaceutically acceptable salt thereof, and pharmaceutically acceptable solvates of either entity, wherein X is CH or N; Y is optionally monousaturated C.sub.3 -C.sub.5 alkylene optionally substituted with C.sub.1 -C.sub.4 alkyl or methylene; R.sup.1 is H; C.sub.1 -C.sub.4 alkyl optionally substituted with C.sub.1 -C.sub.4 alkoxy, OH, NR.sup.5 R.sup.6, CONR.sup.5 R.sup.6, C.sub.3 -C.sub.6 cycloalkyl or aryl; or C.sub.3 -C.sub.6 alkenyl; R.sup.2 is H; C.sub.1 -C.sub.4 alkyl optionally substituted with C.sub.1 -C.sub.4 alkoxy, OH, NR.sup.5 R.sup.6, CONR.sup.5 R.sup.6, C.sub.3 -C.sub.6 cycloalkyl or aryl; or CONR.sup.5 R.sup.6 ; R.sup.3 and R.sup.4 are each independently selected from H; C.sub.1 -C.sub.4 alkyl optionally substituted with NR.sup.5 R.sup.6 ; C.sub.1 -C.sub.4 alkoxy; halo; CONR.sup.5 R.sup.6 and aryl; R.sup.5 and R.sup.6 are each independently selected from H and C.sub.1 -C.sub.4 alkyl; and m and n are each independently 1, 2 or 3; are potent and selective thrombin inhibitors useful in the treatment of, inter alia, deep vein thrombosis; reocclusion following thrombolytic therapy; chronic arterial obstruction; peripheral vascular disease; acute myocardial infarction; unstable angina; atrial fibrillation; thrombotic stroke; transient ischaemic attacks; restenosis and occlusion following angioplasty; or neurodegenerative disorders.

  本发明涉及式（I）的化合物，其中X为CH或N；Y为选择性单不饱和C.sub.3-C.sub.5烷基，可选地取代C.sub.1-C.sub.4烷基或亚甲基；R.sup.1为H；C.sub.1-C.sub.4烷基，可选地取代C.sub.1-C.sub.4烷氧基、OH、NR.sup.5R.sup.6、CONR.sup.5R.sup.6、C.sub.3-C.sub.6环烷基或芳基；或C.sub.3-C.sub.6烯基；R.sup.2为H；C.sub.1-C.sub.4烷基，可选地取代C.sub.1-C.sub.4烷氧基、OH、NR.sup.5R.sup.6、CONR.sup.5R.sup.6、C.sub.3-C.sub.6环烷基或芳基；或CONR.sup.5R.sup.6；R.sup.3和R.sup.4各自独立地选择自H；C.sub.1-C.sub.4烷基，可选地取代NR.sup.5R.sup.6；C.sub.1-C.sub.4烷氧基；卤素；CONR.sup.5R.sup.6和芳基；R.sup.5和R.sup.6各自独立地选择自H和C.sub.1-C.sub.4烷基；m和n各自独立地选择1、2或3；这些化合物是有效和选择性的凝血酶抑制剂，可用于治疗深静脉血栓形成；溶栓治疗后再闭塞；慢性动脉阻塞；周围血管疾病；急性心肌梗塞；不稳定型心绞痛；心房颤动；血栓性卒中；短暂性脑缺血发作；再狭窄和血管成形术后闭塞；或神经退行性疾病的治疗。
• Antithrombotic amidinotetrahydropyridylalanine derivatives
  申请人：Pfizer Inc.

  公开号：US05798352A1

  公开（公告）日：1998-08-25

  This invention is directed to compounds of formula (I), ##STR1## pharmaceutically acceptable salts thereof, and pharmaceutically acceptable solvates of either entity, wherein Y is optionally monounsaturated C.sub.3 -C.sub.5 alkylene optionally substituted with C.sub.1 -C.sub.4 alkyl or methylene; R.sup.1 is H; C.sub.1 -C.sub.4 alkyl optionally substituted with C.sub.1 -C.sub.4 alkoxy, OH, NR.sup.5 R.sup.6, CONR.sup.5 R.sup.6, C.sub.3 -C.sub.6 cycloalkyl or aryl; or C.sub.3 -C.sub.6 alkenyl; R.sup.2 is H; C.sub.1 -C.sub.4 alkyl optionally substituted with C.sub.1 -C.sub.4 alkoxy, OH, NR.sup.5 R.sup.6, CONR.sup.5 R.sup.6, C.sub.3 -C.sub.6 cycloalkyl or aryl; or CONR.sup.5 R.sup.6 ; R.sup.3 and R.sup.4 are each independently selected from H; C.sub.1 -C.sub.4 alkyl optionally substituted with NR.sup.5 R.sup.6 ; C.sub.1 -C.sub.4 alkoxy; halo; CONR.sup.5 R.sup.6 and aryl; aryl is phenyl optionally substituted with one, two or three substituents independently selected from C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, OH, halo and CF.sub.3 ; R.sup.5 and R.sup.6 are each independently selected from H and C.sub.1 -C.sub.4 alkyl; and m and n are each independently 1, 2 or 3; which are potent and selective thrombin inhibitors useful in the treatment of inter alia, deep vein thrombosis; reocclusion following thrombolytic therapy; chronic arterial obstruction; peripheral vascular disease; acute myocardial infarction; unstable angina; atrial fibrillation; thrombotic stroke; transient ischaemic attacks; restenosis and occlusion following angioplasty; or neurodegenerative disorders.

  本发明涉及化合物(I)的配方，其中Y是可选的单不饱和C.sub.3-C.sub.5烷基，可选地取代C.sub.1-C.sub.4烷基或亚甲基; R.sup.1是H; C.sub.1-C.sub.4烷基，可选地取代C.sub.1-C.sub.4烷氧基，OH，NR.sup.5R.sup.6，CONR.sup.5R.sup.6，C.sub.3-C.sub.6环烷基或芳基;或C.sub.3-C.sub.6烯基; R.sup.2是H; C.sub.1-C.sub.4烷基，可选地取代C.sub.1-C.sub.4烷氧基，OH，NR.sup.5R.sup.6，CONR.sup.5R.sup.6，C.sub.3-C.sub.6环烷基或芳基;或CONR.sup.5R.sup.6; R.sup.3和R.sup.4各自独立地选自H; C.sub.1-C.sub.4烷基，可选地取代NR.sup.5R.sup.6; C.sub.1-C.sub.4烷氧基; 卤素; CONR.sup.5R.sup.6和芳基; 芳基是苯基，可选地取代一个，两个或三个取自C.sub.1-C.sub.4烷基，C.sub.1-C.sub.4烷氧基，OH，卤素和CF.sub.3的取代基; R.sup.5和R.sup.6各自独立地选自H和C.sub.1-C.sub.4烷基; m和n各自独立地选自1、2或3; 这些化合物是有效和选择性的凝血酶抑制剂，可用于治疗深静脉血栓形成，溶栓治疗后再闭塞，慢性动脉阻塞，周围血管疾病，急性心肌梗死，不稳定性心绞痛，房颤，血栓性卒中，短暂性缺血性发作，血管成形术后再狭窄和闭塞，或神经退行性疾病的治疗中有用。其中，化合物(I)还包括其药学上可接受的盐和任一实体的药学上可接受的溶剂化物。
• ANTITHROMBOTIC AMIDINOPHENYLALANINE AND AMIDINOPYRIDYLALANINE DERIVATIVES
  申请人：Pfizer Limited

  公开号：EP0728132B1

  公开（公告）日：1997-07-16
• ANTITHROMBOTIC AMIDINOTETRAHYDROPYRIDYLALANINE DERIVATIVES
  申请人：Pfizer Research and Development Company, N.V./S.A.

  公开号：EP0822934A1

  公开（公告）日：1998-02-11
• US5750520A
  申请人：——

  公开号：US5750520A

  公开（公告）日：1998-05-12