4-苯基-1,2,3,4-四氢异喹啉盐酸盐 | 75626-12-9

• 物质功能分类: 医药中间体 - 杂环化合物 - 异喹啉类化合物
• 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: 4-苯基-1,2,3,4-四氢异喹啉盐酸盐
• 英文名称: 4-phenyl-1,2,3,4-tetrahydroisoquinoline
• CAS: 75626-12-9
• 化学式: C₁₅H₁₅N
• mdl: MFCD00848693
• 分子量: 209.291
• InChiKey: OSZMNJRKIPAVOS-UHFFFAOYSA-N

物化性质

• 熔点：
  >215°C (dec.)
• 沸点：
  145-150 °C(Press: 0.6 Torr)
• 密度：
  1.065±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（少许）、水（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  12.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

安全信息

• 海关编码：
  2933499090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Phenyl-1,2,3,4-tetrahydroisoquinoline, HCl
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 4-Phenyl-1,2,3,4-tetrahydroisoquinoline, HCl
CAS number: 75626-12-9

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C15H15N.ClH
Molecular weight: 245.8

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen chloride.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-苯基-1,2,3,4-四氢异喹啉盐酸盐 在 sodium hydride 、 potassium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 4-Phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester
  参考文献：
  名称：

  Synthesis and Antimuscarinic Properties of Quinuclidin-3-yl 1,2,3,4-Tetrahydroisoquinoline-2-carboxylate Derivatives as Novel Muscarinic Receptor Antagonists

  摘要：

  In the course of continuing efforts to develop potent and bladder-selective muscarinic M-3 receptor antagonists, quinuclidin-3-yl 1-aryl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives and related compounds were designed as conformationally restricted analogues of quinuclidin-3-yl benzhydrylcarbamate (8). Binding assays with rat muscarinic receptor subtypes revealed that the quinuclidin-3-yl 1-aryl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives showed high affinities for the M3 receptor, and selectivity for the M3 receptor over the M-2 receptor. Of these derivatives, (+)-(1S,3'R)-quinuclidin-3'-yl 1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate monohydrochloride (9b) exhibited almost the same inhibitory activity against bladder contraction to that of oxybutynin (1), and more than 10-fold selectivity for bladder contraction versus salivary secretion, demonstrating that 9b may be useful for the treatment of symptoms associated with overactive bladder without having side effects such as dry mouth.

  DOI：

  10.1021/jm050099q
• 作为产物：
  描述：

  5-苯基-1,3-恶唑烷-2-硫酮 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 lithium aluminium tetrahydride 、 硫酸 、 sodium methylate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 36.5h， 生成 4-苯基-1,2,3,4-四氢异喹啉盐酸盐
  参考文献：
  名称：

  Oxazolines. 2. 2-Substituted 2-oxazolines as synthons for N-(.beta.-hydroxyethyl)arylalkylamines, intermediates in a synthesis of 1,2,3,4-tetrahydroisoquinolines and 2,3,4,5-tetrahydro-1H-3-benzazepines

  摘要：

  DOI：

  10.1021/jo00132a001

文献信息

• Reduction of isoquinoline and pyridine-containing heterocycles with lithium triethylborohydride (Super-Hydride®)
  作者：Bruce E. Blough、F.Ivy Carroll

  DOI：10.1016/s0040-4039(00)79297-5

  日期：1993.11

  pyridines are effectively reduced to 1,2,3,4-tetrahydroisoquinolines, 1,2,3,4-tetrahydroquinolines and piperidines respectively with lithium triethylborohydride (Super-Hydride®). The mechanism of the reduction was explored by reduction of isoquinoline and pyridine with lithium triethylborodeuteride (Super-Deuteride®).

  用三乙基硼氢化锂将异喹啉，喹啉和吡啶分别有效还原为1,2,3,4-四氢异喹啉，1,2,3,4-四氢喹啉和哌啶。通过用三乙基硼氘化锂（Super-Deuteride®）还原异喹啉和吡啶来探索还原的机理。
• Novel 4-phenyl substituted tetrahydroisoquinolines and therapeutic use thereof
  申请人：Molino F. Bruce

  公开号：US20060111385A1

  公开（公告）日：2006-05-25

  The present invention relates to a method of treating disorders including cognition impairment, generalized anxiety disorder, acute stress disorder, social phobia, simple phobias, pre-menstrual dysphoric disorder, social anxiety disorder, major depressive disorder, eating disorders, obesity, anorexia nervosa, bulimia nervosa, binge eating disorder, substance abuse disorders, chemical dependencies, nicotine addiction, cocaine addiction, alcohol addiction, amphetamine addiction, Lesch-Nyhan syndrome, neurodegenerative diseases, late luteal phase syndrome, narcolepsy, psychiatric symptoms anger, rejection sensitivity, movement disorders, extrapyramidal syndrome, Tic disorder, restless leg syndrome, tardive dyskinesia, sleep related eating disorder, night eating syndrome, stress urinary incontinence, migraine, neuropathic pain, diabetic neuropathy, fibromyalgia syndrome, chronic fatigue syndrome, sexual dysfunction, premature ejaculation, and male impotence. This method involves administering to a patient in need of such treatment a therapeutically effective amount of a disclosed compound. Such compounds are 4-phenyl substituted tetrahydroisoquinolines having the Formula IA, IB, IIA, IIB, IIIA or IIIC as set forth herein.

  本发明涉及一种治疗包括认知障碍、广泛性焦虑障碍、急性应激障碍、社交恐惧症、简单恐惧症、经前期情绪性失调障碍、社交焦虑障碍、重度抑郁障碍、进食障碍、肥胖症、厌食症、暴食症、物质滥用障碍、化学依赖、尼古丁成瘾、可卡因成瘾、酒精成瘾、安非他命成瘾、莱什-尼汉综合征、神经退行性疾病、月经后期综合征、嗜睡症、精神症状愤怒、拒绝敏感性、运动障碍、锥体外症候群、抽动障碍、不安腿综合征、迟发性运动障碍、与睡眠相关的进食障碍、夜间进食综合征、压力性尿失禁、偏头痛、神经痛、糖尿病性神经病变、纤维肌痛综合征、慢性疲劳综合征、性功能障碍、早泄和男性阳痿等多种疾病的方法。该方法涉及向需要此类治疗的患者施用所述化合物的治疗有效量。这些化合物是具有以下IA、IB、IIA、IIB、IIIA或IIIC式的4-苯基取代四氢异喹啉。
• [DE] SUBSTITUIERTE 4-PHENYLTETRAHYDROISOCHINOLINE, VERFAHREN ZU IHRER HERSTELLUNG, IHRE VERWENDUNG ALS MEDIKAMENT, SOWIE SIE ENTHALTENDES MEDIKAMENT<br/>[EN] SUBSTITUTED 4-PHENYLTETRAHYDROISOQUINOLINES, METHOD FOR THE PRODUCTION THEREOF, THEIR USE AS A MEDICAMENT, AND A MEDICAMENT CONTAINING THEM<br/>[FR] 4-PHENYLTETRAHYDRO-ISOQUINOLINES SUBSTITUEES, PROCEDE PERMETTANT DE LES PRODUIRE, LEUR UTILISATION COMME MEDICAMENT ET MEDICAMENT LES CONTENANT
  申请人：SANOFI AVENTIS DEUTSCHLAND

  公开号：WO2006032372A1

  公开（公告）日：2006-03-30

  Die Erfindung betrifft Verbindungen der Formel (I), worin R1 bis R10 die in den Ansprüchen wiedergegebenen Bedeutungen haben. Medikamente, die Verbindungen dieses Typs enthalten, sind nützlich bei der Prävention oder Behandlung diverser Erkrankungen. So lassen sich die Verbindungen unter anderem bei Nierenerkrankungen wie akutem oder chronischem Nierenversagen, bei Störungen der Gallenfunktion, bei Atemstörungen wie Schnarchen oder Schlafapnoen oder bei Schlaganfall einsetzen.

  该发明涉及式(I)的化合物，其中R1至R10具有权利要求中所述的含义。含有这种类型化合物的药物在预防或治疗各种疾病方面是有用的。因此，这些化合物可以用于肾脏疾病如急性或慢性肾衰竭、胆功能紊乱、呼吸障碍如打鼾或睡眠呼吸暂停症或中风等情况。
• SUBSTITUTED 4-PHENYLTETRAHYRDOISOQUINOLINES, PHARMACEUTICAL COMPOSITIONS THEREOF, METHODS FOR THEIR PREPARATION AND THERAPEUTIC USE
  申请人：LANG Hans-Jochen

  公开号：US20070225323A1

  公开（公告）日：2007-09-27

  The present invention relates to substituted 4-phenyltetrahydroisoquinoline compounds of the structure of formula I and pharmaceutical compositions comprising them wherein the R groups are herein defined. These are excellent inhibitors of the sodium-hydrogen exchanger (NHE), in particular of the sodium-hydrogen exchanger of subtype 3 (NHE3). As such these compounds are useful in the treatment of various disorders of the renal and respiratory systems such as acute or chronic renal failure, pulmonary complications, biliary function disorders, respiratory disorders such as snoring or sleep apneas and cardiovascular/central nervous system disorders such as stroke. More specifically, the present invention relates to substituted 4-phenyl-tetrahydroisoquinolines, derivatives thereof and compositions containing them formulated in combination with other compounds which also regulate the intracellular pH environment such as inhibitors of carbonic anhydrase and inhibitors of the transport systems that carry bicarbonate ions, such as of the sodium-bicarbonate co-transporter (NBC) or the sodium-dependent chloride-bicarbonate exchanger

  本发明涉及结构为式I的取代4-苯基四氢异喹啉化合物及包含它们的药物组合物，其中R基在此处定义。这些化合物是优秀的钠-氢交换体（NHE）抑制剂，特别是NHE3亚型的钠-氢交换体。因此，这些化合物在治疗肾脏和呼吸系统的各种疾病方面非常有用，如急性或慢性肾衰竭、肺部并发症、胆功能障碍、呼吸系统疾病如打鼾或睡眠呼吸暂停以及心血管/中枢神经系统疾病如中风。更具体地，本发明涉及取代的4-苯基四氢异喹啉、其衍生物以及含有它们的组合物，该组合物与其他调节细胞内pH环境的化合物一起配制，如碳酸酐酶抑制剂和携带碳酸氢根离子的转运系统的抑制剂，如钠-碳酸氢根共转运体（NBC）或钠依赖性氯化物-碳酸氢根交换体。
• Weinreb amide based synthetic equivalents for convenient access to 4-aryl-1,2,3,4-tetrahydroisoquinolines
  作者：Harikrishna Kommidi、Sivaraman Balasubramaniam、Indrapal Singh Aidhen

  DOI：10.1016/j.tet.2010.03.074

  日期：2010.5

  N-methoxy-N-methyl-N′-benzyl-N′-tert-butyloxy carbonyl glycinamide based on WA functionality were developed for the convenient synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinoline framework. Two simple reactions, N-benzylation and addition of arylmagnesium halide on the WA functionality of the former afforded the key intermediate for convenient synthesis of N-phenylsulfonyl protected 4-aryl-1,2,3,4-tetrahydroisoquinoline

  新的合成的等同物，Ñ甲氧基Ñ甲基Ñ ' -苯磺酰基甘氨酰胺和Ñ甲氧基Ñ甲基Ñ ' -苄基- ñ ' -叔-butyloxy羰基于WA功能甘氨酰胺被用于的方便合成开发4-芳基-1,2,3,4-四氢异喹啉骨架。两个简单的反应，N-苄基化和芳基卤化镁在前者的WA功能上的加成提供了方便合成N的关键中间体-苯磺酰基通过还原和酸促进的环化作用来保护4-芳基-1,2,3,4-四氢异喹啉。对于后者，在WA官能团上添加卤化芳基镁，然后按照相同的方案，以良好的产率直接合成了4-芳基-1,2,3,4-四氢异喹啉。酸促进的环化步骤能够同时去除N -Boc保护。