3-(羟甲基)-3,4-二氢异喹啉-2(1H)-羧酸叔丁酯 | 243858-66-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 中文名称: 3-(羟甲基)-3,4-二氢异喹啉-2(1H)-羧酸叔丁酯
• 英文名称: N-tert-butyloxycarbonyl-1,2,3,4-tetrahydroisoquinoline-3-methanol
• 英文别名: N-(tert-butyloxycarbonyl)-3-isoquinolinemethanol；3-Hydroxymethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester；(R)-tert-butyl 3-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate；N-tert-butyloxycarbonyl-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline；tert-butyl 3-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate；tert-butyl 3-(hydroxymethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 243858-66-4
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: FPIKXSHVYZIKOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(羟甲基)-3,4-二氢异喹啉-2(1H)-羧酸叔丁酯 在 吡啶 、 草酰氯 、 4-乙酰氨基苯磺酰叠氮 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 13.83h， 生成 (E)-N-(1,3-dioxo-2-diazobutyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxaldehyde-O-methyloxime
  参考文献：
  名称：

  Intramolecular Aziridination:  Decomposition of Diazoamides with Tethered Imino Bonds

  摘要：

  Of three possible mechanistic pathways, tethered oximino ethers react intramolecularly with diazoamides to produce a diazabicyclo[5.1.0]hexane aziridine containing skeleton. Several acyclic and cyclic templates were synthesized and reacted with rhodium catalysts to prepare their corresponding annulated aziridines. Anomalous behavior was discovered with the piperidine template, resulting in an aziridination occurring during the attempted diazo-transfer reaction, rather than the catalyzed carbenoid reaction.

  DOI：

  10.1021/ol990750h
• 作为产物：
  描述：

  1,2,3,4-四氢-3-异喹啉羧酸 盐酸盐 在 sodium hydroxide 、 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 12.0h， 生成 3-(羟甲基)-3,4-二氢异喹啉-2(1H)-羧酸叔丁酯
  参考文献：
  名称：

  Intramolecular Aziridination:  Decomposition of Diazoamides with Tethered Imino Bonds

  摘要：

  Of three possible mechanistic pathways, tethered oximino ethers react intramolecularly with diazoamides to produce a diazabicyclo[5.1.0]hexane aziridine containing skeleton. Several acyclic and cyclic templates were synthesized and reacted with rhodium catalysts to prepare their corresponding annulated aziridines. Anomalous behavior was discovered with the piperidine template, resulting in an aziridination occurring during the attempted diazo-transfer reaction, rather than the catalyzed carbenoid reaction.

  DOI：

  10.1021/ol990750h

文献信息

• Tetrahydroisoquinolinealkanol derivatives and pharmaceutical
  申请人：SK Corporation

  公开号：US05955471A1

  公开（公告）日：1999-09-21

  The present invention provides novel 1,2,3,4-tetrahydroisoquinoline carbamate and thiocarbamate derivatives represented by Formula I ##STR1## wherein: X.sub.1 and X.sub.2 are the same or different from each other and independently represent a a member selected from the group consisting of hydrogen, alkyl, alkoxy, thioalkoxy, halogen, hydroxy, nitro and trifluorocarbon; Y is a member selected from the group consisting of oxygen and sulfur; R.sub.1 is a member selected from the group consisting of hydrogen, alkyl, arylalkyl, and CONHR' where R' is selected from the group consisting of hydrogen, alkyl, arylalkyl and aryl; R.sub.2 and R.sub.3 are the same or different from each other and independently represent a member selected from the group consisting of hydrogen, alkyl, arylalkyl, and cycloalkyl, or R.sub.2 and R.sub.3 may form a 5 to 7-membered ring together with the nitrogen atom to which they are bonded; R.sub.4 is a member selected from the group consisting of hydrogen or lower alkyl; and nontoxic pharmacologically acceptable salts thereof. Compounds are useful in the treatment of central nervous system disorders, including depression.

  本发明提供了新颖的1,2,3,4-四氢异喹啉氨基甲酸酯和硫代氨基甲酸酯衍生物，其结构如式I所示 ##STR1## 其中：X1和X2彼此相同或不同，独立地表示氢、烷基、烷氧基、硫代烷氧基、卤素、羟基、硝基和三氟甲基中的一种；Y表示氧或硫；R1表示氢、烷基、芳基烷基和CONHR'中的一种，其中R'表示氢、烷基、芳基烷基和芳基中的一种；R2和R3彼此相同或不同，独立地表示氢、烷基、芳基烷基和环烷基中的一种，或者R2和R3可以与它们所连接的氮原子一起形成5至7元环；R4表示氢或低级烷基；以及其无毒的药理学上可接受的盐。这些化合物可用于治疗中枢神经系统疾病，包括抑郁症。
• Substituted Tetrahydroisoquinolines as Beta-secretase Inhibitors
  申请人：Thompson Lorin A.

  公开号：US20080153868A1

  公开（公告）日：2008-06-26

  There is provided a series of tetrahydroisoquinoline diaminopropane compounds of Formula (I) or a stereoisomer; or a pharmaceutically acceptable salt thereof, wherein R, R 8 and R 9 are as defined herein, their pharmaceutical compositions and methods of use. These compounds inhibit the processing of amyloid precursor protein (APP) by β-secretase and, more specifically, inhibit the production of Aβ-peptide. The present disclosure is directed to compounds useful in the treatment of neurological disorders related to β-amyloid production, such as Alzheimer's disease and other conditions affected by anti-amyloid activity.

  提供一系列Formula (I)的四氢异喹啉二氨基丙烷化合物或其立体异构体；或其药学上可接受的盐，其中R，R8和R9如本文所定义，它们的药物组合物和使用方法。这些化合物抑制β-分泌酶对淀粉样前体蛋白（APP）的加工，更具体地说，抑制Aβ肽的产生。本公开涉及用于治疗与β-淀粉样蛋白产生相关的神经系统疾病的化合物，如阿尔茨海默病和其他受抗淀粉样活性影响的疾病。
• ORGANIC COMPOUNDS
  申请人：Neubert Alan

  公开号：US20090181928A1

  公开（公告）日：2009-07-16

  Compounds of the formula are inhibitors of protein tyrosine phosphatases (PTPases) and, thus, may be employed for the treatment of conditions mediated by PTPase activity. The compounds of the present invention may also be employed as inhibitors of other enzymes characterized with a phosphotyrosine binding region such as the SH2 domain. Accordingly, the compounds of formula (I) may be employed for prevention and/or treatment of insulin resistance associated with obesity, glucose intolerance, diabetes mellitus, hypertension and ischemic diseases of the large and small blood vessels, conditions that accompany type-2 diabetes, including hyperlipidemia, hypertriglyceridemia, atherosclerosis, vascular restenosis, irritable bowel syndrome, pancreatitis, adipose cell tumors and carcinomas such as liposarcoma, dyslipidemia, and other disorders where insulin resistance is indicated. In addition, the compounds of the present invention may be employed to treat and/or prevent cancer, osteoporosis, musculoskeletal, neurodegenerative and infectious diseases, and diseases involving inflammation and the immune system.

  公式的化合物是蛋白酪氨酸磷酸酶（PTPases）的抑制剂，因此可用于治疗由PTPase活性介导的疾病。本发明的化合物也可用作其他酶的抑制剂，这些酶具有磷酸酪氨酸结合区域，如SH2结构域。因此，公式（I）的化合物可用于预防和/或治疗与肥胖、葡萄糖不耐受、糖尿病、高血压以及大、小血管缺血性疾病有关的胰岛素抵抗。这些疾病包括高脂血症、高三酰甘油血症、动脉粥样硬化、血管再狭窄、肠易激综合征、胰腺炎、脂肪细胞肿瘤和脂肪肉瘤等癌症，以及其他显示胰岛素抵抗的疾病。此外，本发明的化合物可用于治疗和/或预防癌症、骨质疏松症、肌肉骨骼、神经退行性和传染性疾病，以及涉及炎症和免疫系统的疾病。
• TETRAHYDRO ISOQUINO LINEALKANOL DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME
  申请人：SK Corporation

  公开号：EP1149079B1

  公开（公告）日：2004-04-21
• Investigations concerning the organolanthanide and group 3 metallocene-catalyzed cyclization–functionalization of nitrogen-containing dienes
  作者：Gary A. Molander、Jan Antoinette C. Romero

  DOI：10.1016/j.tet.2005.01.048

  日期：2005.3

  Organolanthanide catalyzed cyclization-silylation of nitrogen-containing polyunsaturated systems allows access to core structures commonly found in naturally occurring alkaloids. Nitrogen-containing dienes with various substitution patterns were investigated. The method was most successful for substrates with terminal alkenes. Cyclization upon pendant 1,1-disubstituted olefins was not realized under various conditions. Interestingly, sterically hindered sulfonamides, which were previously believed to render the catalyst inactive, were actually compatible with the catalyst, thus affording the cyclized products after prolonged reaction times. Variations using fused ring systems were also investigated. (C) 2005 Elsevier Ltd. All rights reserved.