3,4-二氢-6,7-二羟基异喹啉 | 4602-83-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢异喹啉
• 中文名称: 3,4-二氢-6,7-二羟基异喹啉
• 中文别名: 6,7-二羟基-3,4-二氢异喹啉
• 英文名称: 3,4-dihydroisoquinoline-6,7-diol
• 英文别名: 6,7-Dihydroxy-3,4-dihydro-isochinolin
• CAS: 4602-83-9
• 化学式: C₉H₉NO₂
• mdl: MFCD00143490
• 分子量: 163.176
• InChiKey: PWCQVMIYUGOTLG-UHFFFAOYSA-N

物化性质

• 熔点：
  244-248 °C
• 沸点：
  290.25°C (rough estimate)
• 密度：
  1.2021 (rough estimate)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• 稳定性/保质期：

  在常温常压下稳定，避免与不相容材料接触。它会与强氧化剂反应。

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36,S37,S39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933499090

SDS

Name:	6 7-Dihydroxy-3 4-Dihydroisoquinoline 98% Material Safety Data Sheet
Synonym:	None known
CAS:	4602-83-9

Section 1 - Chemical Product MSDS Name:6 7-Dihydroxy-3 4-Dihydroisoquinoline 98% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4602-83-9	6,7-Dihydroxy-3,4-Dihydroisoquinoline	98	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 4602-83-9: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: yellow to brown
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 236.00 - 241.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: soluble in hot water
Specific Gravity/Density:
Molecular Formula: C9H9NO2
Molecular Weight: 163.18

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 4602-83-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
6,7-Dihydroxy-3,4-Dihydroisoquinoline - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 4602-83-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 4602-83-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 4602-83-9 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3,4-二氢-6,7-二羟基异喹啉 、 氘代甲醇 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以66%的产率得到d₆-6,7-dimethoxy-3,4-dihydroisoquinoline
  参考文献：
  名称：

  [EN] A NOVEL PROCESS FOR PREPARATION OF DEUTETRABENAZINE
  [FR] NOUVEAU PROCÉDÉ DE PRÉPARATION DE DEUTÉTRABÉNAZINE

  摘要：

  一种用于制备Deutetrabenazine ((RR, SS)-l,3,4,6,7-llb-六氢-9,10-二(甲氧基-d6)-3-(2-甲基丙基)-2H-苯并[a]喹啉-2-酮)的新型工艺包括将式III的N-(2-(3,4-二羟基苯基)-乙基)-甲酰胺化合物与氘化甲醇(CD3OD或CD3OH)甲基化，得到式IV的d6-N-(2-(3,4-二甲氧基苯基)-乙基)-甲酰胺化合物；在脱水剂存在下将d6-N-(2-(3,4-二甲氧基苯基)-乙基)-甲酰胺环化，得到式V的d6-6,7-二甲氧基-3,4-二氢异喹啉化合物；将式V的d6-6,7-二甲氧基-3,4-二氢异喹啉化合物与式VI的2-乙酰-N,N,N,4-四甲基-1-戊胺碘化物发生反应。

  公开号：

  WO2019150387A1
• 作为产物：
  描述：

  mellpaladine A 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 以0.65 mg的产率得到3,4-二氢-6,7-二羟基异喹啉
  参考文献：
  名称：

  Mellpaladines和dopargimine，来自Palauan Didemnidae被膜的新型神经活​​性胍生物碱

  摘要：

  新的胍类生物碱dopargimine（1）和mellpaladines A-C（2 - 4）从帛琉Didemnidae囊动物中分离。的结构1 - 4分别鉴定的光谱数据与化学反应一起的基础上。的推定的生物合成积木1 - 4，4-胍基丁酸（5），和二聚多巴胺聚硫，以及lissoclibadins 11（图6a）和12（6B）也分离。化合物1 - 3结合于突触受体，和脑室内注射后调制的小鼠的行为简档。

  DOI：

  10.1016/j.tet.2016.09.051

文献信息

• [EN] NOVEL DERIVATIVES OF A 3,4-DIHYDROISOQUINOLINE-3-CARBOXYLIC ACID HAVING ANTI-CANCER PROPERTIES, A METHOD FOR THEIR SYNTHESIS, PHARMACEUTICAL COMPOSITIONS COMPRISING SAID DERIVATIVES, AND THEIR USE<br/>[FR] NOUVEAUX DÉRIVÉS D'UN ACIDE 3,4-DIHYDROISOQUINOLINE-3-CARBOXYLIQUE AYANT DES PROPRIÉTÉS ANTICANCÉREUSES, LEUR PROCÉDÉ DE SYNTHÈSE, COMPOSITIONS PHARMACEUTIQUES COMPRENANT LESDITS DÉRIVÉS, ET LEUR UTILISATION
  申请人：NARODOWY INST ZDROWIA PUBLICZNEGO PAŃSTWOWY ZAKŁAD HIGIENY

  公开号：WO2015015420A1

  公开（公告）日：2015-02-05

  The object of the invention is 3,4-dihydroisoquinoline derivative of structure represented by formula I, wherein R1is selected from the group consisting of H, COOEt, COOH, COOBn; R2 is selected from the group consisting of H, COOEt, COOH, COOBn; R3is selected from the group consisting of OH, OBn; R4is selected from the group consisting of OH, H, OBn; Rsis selected from the group consisting of OH, OBn; and isomers, salts, hydrates and solvates thereof, as well as the method of preparation thereof; pharmaceutical composition comprising the above mentioned derivative and use thereof.

  该发明的对象是由式I表示的结构的3,4-二氢异喹啉衍生物，其中R1从H、COOEt、COOH、COOBn组成的群体中选择；R2从H、COOEt、COOH、COOBn组成的群体中选择；R3从OH、OBn组成的群体中选择；R4从OH、H、OBn组成的群体中选择；Rs从OH、OBn组成的群体中选择；以及其异构体、盐、水合物和溶剂合物，以及其制备方法；包括上述衍生物的药用组合物及其用途。
• PHARMACEUTICAL COMPOUNDS
  申请人：Duffield Andrew John

  公开号：US20100087475A1

  公开（公告）日：2010-04-08

  This application describes substituted 1,3,4,6,7,11b-hexahydro-benzo(a)quinolizine compounds, pharmaceutical compositions containing them, processes for making them and their therapeutic methods.

  该应用程序描述了取代的1,3,4,6,7,11b-六氢苯并(a)喹啉化合物，含有它们的药物组合物，制备它们的方法以及它们的治疗方法。
• [EN] PROCESS FOR PREPARING TETRABENAZINE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE TÉTRABÉNAZINE
  申请人：ENALTEC LABS PVT LTD

  公开号：WO2012081031A1

  公开（公告）日：2012-06-21

  A substantially pure crystalline form A of tetrabenazine compound of structural formula I and processes for the preparation thereof is provided.

  提供了结构式I的四苯酮化合物的基本纯结晶形式A及其制备方法。
• Decahydro-8H-isoquino[2,1-g][1,6]naphthyridine and decahydrobenzo[a]pyrrolo[2,3-e]quinolizine derivatives
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0524004A1

  公开（公告）日：1993-01-20

  Compounds of the formula wherein:    X and Y are independently hydrogen; hydroxy; lower alkyl of 1-6 carbon atoms; lower alkoxy of 1-6 carbon atoms; or halo; or X and Y when adjacent and taken together are methylenedioxy or ethylene-1,2-dioxy;    R is lower alkyl of 1-6 carbon atoms; cycloalkyl of 3-8 carbon atoms; phenyl or phenyl lower alkyl in which any phenyl group may be optionally substituted by one or two substituents chosen from the group consisting of halo, lower alkyl of 1-4 carbon atoms and lower alkoxy of 1-4 carbon atoms; or -ANHSO₂R¹; wherein A is lower alkylene of 1-6 carbon atoms; and R¹ is lower alkyl of 1-6 carbon atoms or -NR²R³; wherein       R² and R³ are independently hydrogen or lower alkyl of 1-6 carbon atoms, or R² and R³ taken together are cycloalkyl of 3-8 carbon atoms; and    n is 1 or 2;    and the pharmaceutically acceptable salts thereof, are useful as α₂-adrenoceptor antagonists, in particular as peripherally selective α₂ -adrenoceptor antagonists.

  该式化合物中：X和Y分别是氢；羟基；1-6个碳原子的低烷基；1-6个碳原子的低烷氧基；或卤素；或当相邻时一起取为亚甲二氧基或乙烯-1,2-二氧基；R是1-6个碳原子的低烷基；3-8个碳原子的环烷基；苯基或苯基低烷基，其中任何苯基可以选择性地被来自卤素、1-4个碳原子的低烷基和1-4个碳原子的低烷氧基的一种或两种取代基取代；或-ANHSO₂R¹；其中A是1-6个碳原子的低烷基；R¹是1-6个碳原子的低烷基或-NR²R³；其中R²和R³分别是氢或1-6个碳原子的低烷基，或R²和R³一起取为3-8个碳原子的环烷基；n为1或2；以及其药用盐，可用作α₂-肾上腺素受体拮抗剂，特别是外周选择性α₂-肾上腺素受体拮抗剂。
• [EN] NOVEL PROCESS FOR PREPARATION OF TETRABENAZINE AND DEUTETRABENAZINE<br/>[FR] NOUVEAU PROCÉDÉ DE PRÉPARATION DE LA TÉTRABÉNAZINE ET DE LA DEUTÉTRABÉNAZINE
  申请人：LUPIN LTD

  公开号：WO2017182916A1

  公开（公告）日：2017-10-26

  The present invention provides process for preparation of dihydroxy benzoquinoline compound (III) comprising reacting dihydroxy isoquinoline compound (IV) or a salt thereof with (2-acetyl-4-methyl-pentyl)-trimethyl-ammonium iodide (V) and further 5 converting it to tetrabenazine (I) and deutetrabenazine (II).

  本发明提供了一种制备二羟基苯醌啉化合物(III)的方法，包括将二羟基异喹啉化合物(IV)或其盐与(2-乙酰基-4-甲基戊基)-三甲基铵碘(V)反应，并进一步将其转化为四苯嗪(I)和氘代四苯嗪(II)的过程。