tert-butyl 5-[(dimethylamino)methyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate | 601517-13-9

• 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: tert-butyl 5-[(dimethylamino)methyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 601517-13-9
• 化学式: C₁₇H₂₆N₂O₂
• 分子量: 290.406
• InChiKey: YIWWRZYELHWZOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-[(dimethylamino)methyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到N,N-dimethyl-1-(1,2,3,4-tetrahydroisoquinolin-5-yl)methanamine;hydrochloride
  参考文献：
  名称：

  Synthesis of substituted 5-aminomethyl tetrahydro-isoquinolines and dihydro-isoindoles

  摘要：

  The synthesis of ten substituted aminomethylene tetrahydro-isoquinolines is described, proceeding in eight steps from 5-hydroxyisoquinoline via reductive amination of N-Boc tetrahydro-isoquinoline 5-carboxaldehyde. Likewise, reductive amination was used to prepare four substituted dihydro-isoindoles from the corresponding aldehyde. The dihydro-isoindole ring system was conveniently accessed via a 2+2+2 cycloaddition reaction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.095
• 作为产物：
  描述：

  5-羟基-1,2,3,4-四氢异喹啉 在 sodium hydroxide 、 N-苯基双(三氟甲烷磺酰)亚胺 、 二异丁基氢化铝 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 60.5h， 生成 tert-butyl 5-[(dimethylamino)methyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate
  参考文献：
  名称：

  Synthesis of substituted 5-aminomethyl tetrahydro-isoquinolines and dihydro-isoindoles

  摘要：

  The synthesis of ten substituted aminomethylene tetrahydro-isoquinolines is described, proceeding in eight steps from 5-hydroxyisoquinoline via reductive amination of N-Boc tetrahydro-isoquinoline 5-carboxaldehyde. Likewise, reductive amination was used to prepare four substituted dihydro-isoindoles from the corresponding aldehyde. The dihydro-isoindole ring system was conveniently accessed via a 2+2+2 cycloaddition reaction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.095

文献信息

• Compounds useful in therapy
  申请人：Pfizer Inc.

  公开号：US20040029859A1

  公开（公告）日：2004-02-12

  Compounds of formula (I): 1 or pharmaceutically acceptable salts or solvates thereof, wherein R 1 represents C 1-4 alkyl; R 2 represents halo, C 1-4 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyloxy, —SO 2 (C 1-4 alkyl), optionally substituted C 1-4 alkyloxy, Het or —OHet; R 3 represents a bicyclic group of the formula 2 wherein X and Y are selected from C and N, provided that at least one is C; Ring A together with X and Y represents a 5- or 6-membered aromatic ring containing 0, 1, 2 or 3 nitrogen atoms in the ring; n is), 1 or 2 L represents a direct link, C 1-4 alkylene or C 1-4 alkoxyalkylene; R 4 represents H, —NR 5 R 6 , C 3-6 cycloalkyl, —OR 7 , Het 1 or Het 4 ; R 5 and R 6 are independently selected from H, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 alkylene, —SO 2 (C 1-4 alkyl) and optionally substituted C 1-4 alkyl R 7 is selected from H, C 1-4 alkyl, C 1-4 alkoxyalkyl, C 3-6 cycloalkyl, Het 2 and C 1-4 alkyl-Het 3 ; R 8 is H or C 1-4 alkyl; Het, Het 1 , Het 2 and Het 3 independently represent an optionally substituted 4 to 7 membered saturated heterocyclic group which may be mono- or bi-cyclic and which contains one or more heteroatoms selected from N, O or S; Het 4 represents an optionally substituted 5 or 6 membered unsaturated heterocyclic group containing one or more heteroatoms selected from N, O or S; R 9 is H or C 1-4 alkyl; R 10 and R 11 are independently selected from H and C 1-4 alkyl; are useful in the treatment of hypertension, myocardial infarction, male erectile dysfunction (MED), hyperlipidaemia, cardiac arrhythmia, glaucoma and benign prostatic hyperplasia (BPH). They also find utility in the treatment of female sexual arousal dysfunction (FSAD).

  式(I)的化合物：1或其药学上可接受的盐或溶剂化合物，其中R1代表C1-4烷基；R2代表卤素、C1-4烷基、C3-6环烷基、C3-6环烷氧基、—SO2(C1-4烷基)、可选取代的C1-4烷氧基、Het或—OHet；R3代表式2的双环基，其中X和Y选择自C和N，但至少有一个是C；环A与X和Y一起表示含0、1、2或3个氮原子的5-或6成员芳香环；n为0、1或2；L表示直接链接、C1-4烷基或C1-4烷氧基烷基；R4代表H、—NR5R6、C3-6环烷基、—OR7、Het1或Het4；R5和R6独立选择自H、C3-6环烷基、C3-6环烷基-C1-4烷基、—SO2(C1-4烷基)和可选取代的C1-4烷基；R7选择自H、C1-4烷基、C1-4烷氧基烷基、C3-6环烷基、Het2和C1-4烷基-Het3；R8为H或C1-4烷基；Het、Het1、Het2和Het3独立表示可选取代的4到7成员饱和杂环基，可以是单环或双环，并且包含一个或多个选择自N、O或S的杂原子；Het4表示可选取代的5或6成员不饱和杂环基，其中包含一个或多个选择自N、O或S的杂原子；R9为H或C1-4烷基；R10和R11独立选择自H和C1-4烷基；它们在治疗高血压、心肌梗塞、男性勃起功能障碍（MED）、高脂血症、心脏心律失常、青光眼和良性前列腺增生（BPH）方面有用。它们还在治疗女性性唤起障碍（FSAD）方面发现有用。
• QUINAZOLINE COMPOUNDS USEFUL IN THERAPY
  申请人：Pfizer Limited

  公开号：EP1483257B1

  公开（公告）日：2006-09-13
• US6936619B2
  申请人：——

  公开号：US6936619B2

  公开（公告）日：2005-08-30
• Synthesis of substituted 5-aminomethyl tetrahydro-isoquinolines and dihydro-isoindoles
  作者：M. Jonathan Fray、Paul Allen、Paul R. Bradley、Clare E. Challenger、Michael Closier、Tim J. Evans、Mark L. Lewis、John P. Mathias、Carly L. Nichols、Yvonne M. Po-Ba、Hayley Snow、Mark H. Stefaniak、Hannah V. Vuong

  DOI：10.1016/j.tet.2006.04.095

  日期：2006.7

  The synthesis of ten substituted aminomethylene tetrahydro-isoquinolines is described, proceeding in eight steps from 5-hydroxyisoquinoline via reductive amination of N-Boc tetrahydro-isoquinoline 5-carboxaldehyde. Likewise, reductive amination was used to prepare four substituted dihydro-isoindoles from the corresponding aldehyde. The dihydro-isoindole ring system was conveniently accessed via a 2+2+2 cycloaddition reaction. (c) 2006 Elsevier Ltd. All rights reserved.