1,2,3,4-四氢喹啉-2-羧酸甲酯盐酸盐 | 78348-26-2

• 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
• 中文名称: 1,2,3,4-四氢喹啉-2-羧酸甲酯盐酸盐
• 英文名称: 1,2,3,4-tetrahydroquinoline-2-carboxylic acid methyl ester hydrochloride
• 英文别名: methyl 1,2,3,4-tetrahydroquinoline-2-carboxylate hydrochloride；2-(methoxycarbonyl)tetrahydroquinoline hydrochloride；1,2,3,4-tetrahydro-quinoline-2-carboxylic acid methyl ester; hydrochloride；1,2,3,4-Tetrahydro-chinolin-2-carbonsaeure-methylester; Hydrochlorid；methyl 1,2,3,4-tetrahydroquinoline-2-carboxylate;hydrochloride
• CAS: 78348-26-2
• 化学式: C₁₁H₁₃NO₂*ClH
• 分子量: 227.691
• InChiKey: GZCFAFBVBOGXRN-UHFFFAOYSA-N

物化性质

• 熔点：
  170 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -2.63
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  42.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Name:	Methyl 1 2 3 4-tetrahydroquinoline-2-carboxylate hydrochloride 95+% Material Safety Data Sheet
Synonym:
CAS:	78348-26-2

Section 1 - Chemical Product MSDS Name:Methyl 1 2 3 4-tetrahydroquinoline-2-carboxylate hydrochloride 95+% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
78348-26-2	Methyl 1,2,3,4-tetrahydroquinoline-2-c	95+%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.Moisture sensitive.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. Wash mouth out with 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:
Treat symptomatically and supportively.

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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.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

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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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Store under nitrogen.

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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# 78348-26-2: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: cream
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 190 - 195 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C11H14ClNO2
Molecular Weight: 228

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials, exposure to moist air or water.
Incompatibilities with Other Materials:
Strong oxidizing agents, bases, amines.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 78348-26-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 1,2,3,4-tetrahydroquinoline-2-carboxylate hydrochloride - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 78348-26-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 78348-26-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 78348-26-2 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：

  1,2,3,4-四氢喹啉-2-羧酸甲酯盐酸盐 在 sodium hydroxide 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 (R)-methyl 1,2,3,4-tetrahydroquinoline-2-carboxylate
  参考文献：
  名称：

  强大的双重Bcl-2 / Bcl-x L拮抗剂的多千克合成。1.酸部分的制造和一些关键反应的发展

  摘要：

  我们在两篇论文中描述了我们对候选药物1的开发过程。该手稿侧重于千克量的酸前体2的合成，以提供批次的材料用于临床前研究和首次人体临床试验。我们的方法依赖于手性拆分以提供所需的立体中心，低温羧化和通过Suzuki偶联制备的氯化物衍生物26的N-烷基化。还讨论了进一步的努力，以改进那些可能成为更大规模问题的关键步骤。

  DOI：

  10.1021/acs.oprd.9b00364
• 作为产物：
  描述：

  喹哪啶酸 在 盐酸 、 palladium on activated charcoal 、 氢气 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 20.0~50.0 ℃ 、3.0 MPa 条件下， 反应 20.17h， 生成 1,2,3,4-四氢喹啉-2-羧酸甲酯盐酸盐
  参考文献：
  名称：

  强大的双重Bcl-2 / Bcl-x L拮抗剂的多千克合成。1.酸部分的制造和一些关键反应的发展

  摘要：

  我们在两篇论文中描述了我们对候选药物1的开发过程。该手稿侧重于千克量的酸前体2的合成，以提供批次的材料用于临床前研究和首次人体临床试验。我们的方法依赖于手性拆分以提供所需的立体中心，低温羧化和通过Suzuki偶联制备的氯化物衍生物26的N-烷基化。还讨论了进一步的努力，以改进那些可能成为更大规模问题的关键步骤。

  DOI：

  10.1021/acs.oprd.9b00364

文献信息

• (1S)-1-(Aminomethyl)-2-(arylacetyl)-1,2,3,4-tetrahydroisoquinoline and heterocycle-condensed tetrahydropyridine derivatives: members of a novel class of very potent .kappa. opioid analgesics
  作者：Vittorio Vecchietti、Geoffrey D. Clarke、Roberto Colle、Giuseppe Giardina、Giuseppe Petrone、Massimo Sbacchi

  DOI：10.1021/jm00112a042

  日期：1991.8

  of compounds by using X-ray and 1H NMR analyses. The same absolute configuration (S) at the chiral center of the active (-) enantiomers was determined by X-ray crystallographic analysis. A varied degree of kappa receptor selectivity was a feature of this novel class of antinociceptive agents (mu/kappa ratio from 44 to 950 according to the nature of the basic moiety). SAR analysis indicated that the presence

  一类新型κ阿片类镇痛药1-（氨基甲基）-2-（芳基乙酰基）-1,2,3,4-四氢异喹啉和（氨基甲基）-N-（芳基乙酰基）的合成及构效关系（SAR）描述了-4,5,6,7-四氢噻吩并吡啶++。这些化合物是由苯或噻吩环在最近描述的化合物1的哌啶核上的缩合形式正式衍生的，作为抗伤害感受药的效力比原先的先导化合物强3至7倍，并且作用时间更长。通过使用X射线和1H NMR分析，对于此类化合物也发现了大约60度的类似N2-C1-C9-N10药效基团扭转角。通过X射线晶体学分析确定活性（-）对映异构体的手性中心的相同绝对构型（S）。这种新型的抗伤害感受药具有不同程度的κ受体选择性（根据基本部分的性质，mu / kappa比率从44到950）。SAR分析表明，芳香化部分对位和/或间位的吸电子和亲脂性取代基以及吡咯烷基和二甲基氨基碱性基团是优化生物活性所必需的。迄今为止，铅化合物28、30和48是最有效的镇痛药（ED50约为0
• Bicyclic .alpha.-iminocarboxylic acid compounds having hypotensive
  申请人：Hoechst Aktiengesellschaft

  公开号：US04595675A1

  公开（公告）日：1986-06-17

  What are disclosed are indole, quinoline and isoquinoline compounds of the formula ##STR1## in which n denotes 0 or 1, m denotes 1 or 2, but (n+m).ltoreq.2, A together with the bridgehead carbon atoms denotes a benzene or a cyclohexane ring, Y.sub.1 denotes hydrogen, lower alkanoyl or lower cycloalkanoyl, benzoyl nicotinoyl or a radical of the formula II, and Y.sub.2 denotes methyl, amino, lower alkanoylamino, lower cycloalkanoylamino, benzoylamino or nicotinoylamino, and salts thereof, useful as hypotensive agents, and methods for making the same.

  揭示的是式子##STR1##中的吲哚，喹啉和异喹啉化合物，其中n表示0或1，m表示1或2，但(n+m)≤2，A与桥头碳原子一起表示苯环或环己烷环，Y.sub.1表示氢，低烷酰基或低环烷酰基，苯甲酰基，烟酰甲酰基或式子II的基团，Y.sub.2表示甲基，氨基，低烷酰基氨基，低环烷酰基氨基，苯甲酰氨基或烟酰甲酰氨基，以及其盐，作为降压剂使用，并提供制备方法。
• Novel heterocyclic compound
  申请人：Kodo Toru

  公开号：US20070191447A1

  公开（公告）日：2007-08-16

  A drug having a high affinity for benzodiazepine ω 3 receptors and showing curative and preventive effects for anxiety and depression, which comprises as the active ingredient, for example, a compound of the formula (1): wherein R 1 and R 2 are independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, etc., R 3 and R 4 are independently a hydrogen atom, an optionally substituted alkyl group, etc., R 5 , R 6 , R 7 and R 8 are independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, etc., X is an oxygen atom, a sulfur atom, NR 10 , etc. (in which R 10 is a hydrogen atom, an optionally substituted alkyl group, etc.)

  一种对苯二氮平ω3受体具有高亲和力，对焦虑和抑郁具有治疗和预防效果的药物，其包括作为活性成分的化合物，例如式（1）的化合物： 其中R1和R2分别为氢原子，可选取代烷基，可选取代芳基等； R3和R4分别为氢原子，可选取代烷基等； R5、R6、R7和R8分别为氢原子，可选取代烷基，可选取代芳基等； X为氧原子、硫原子、NR10等（其中R10为氢原子、可选取代烷基等）。
• NOVEL HETEROCYCLIC COMPOUND
  申请人：Dainippon Sumitomo Pharma Co., Ltd.

  公开号：EP1719761A1

  公开（公告）日：2006-11-08

  A drug having a high affinity for benzodiazepine ω3 receptors and showing curative and preventive effects for anxiety and depression, which comprises as the active ingredient, for example, a compound of the formula (1): wherein R1 and R2 are independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, etc., R3 and R4 are independently a hydrogen atom, an optionally substituted alkyl group, etc., R5, R6, R7 and R8 are independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, etc., X is an oxygen atom, a sulfur atom, NR10, etc. (in which R10 is a hydrogen atom, an optionally substituted alkyl group, etc.)

  一种对苯二氮卓ω3 受体具有高亲和力并对焦虑症和抑郁症具有治疗和预防作用的药物，其活性成分包括例如式（1）的化合物： 其中 R1 和 R2 独立地为氢原子、任选取代的烷基、任选取代的芳基等、 R3 和 R4 独立地为氢原子、任选取代的烷基等、 R5、R6、R7 和 R8 独立地为氢原子、任选取代的烷基、任选取代的芳基等、 X 是氧原子、硫原子、NR10 等（其中 R10 是氢原子、任选取代的烷基等）
• Tricyclic Quinoxalinediones: 5,6-Dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-diones and 6,7-Dihydro-1H,5H-pyrido[1,2,3-de]quinoxaline-2,3-diones as Potent Antagonists for the Glycine Binding Site of the NMDA Receptor
  作者：Ryu Nagata、Norihiko Tanno、Toru Kodo、Nobuyuki Ae、Hiroshi Yamaguchi、Tamiki Nishimura、Fujio Antoku、Tohru Tatsuno、Terufumi Kato

  DOI：10.1021/jm00049a015

  日期：1994.11

  A series of tricyclic quinoxalinediones, 5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-diones and 6,7-dihydro-1H,5H-pyrido[1,2,3-de]quinoxaline-2,3-diones, were synthesized and was evaluated for their affinity for the glycine binding site of the NMDA receptor using a [H-3]- 5,7-dichlorokynurenic acid binding assay. The six-membered ring-fused tricyclic quinoxalinedione 18g (K-i = 9.9 nM) displayed high affinity for the glycine site. The anilide derivative 20g (K-i = 2.6 nM) was 4-fold more potent than 18g and as potent as L-689,560, one of the most potent glycine antagonists so far prepared. Although the carboxylic acid derivative of the corresponding five-membered ring-fused tricyclic quinoxalinedione 18e (K-i = 7.3 nM) had affinity comparable to that of 18g, the anilide derivative 20e largely decreased in the affinity in contrast to 20g. Enantiomers 23g, 24g, 25g, and 26g were prepared and tested. Only the S enantiomer 25g (K-i = 0.96 nM) retained the affinity among the anilide derivatives, whereas both enantiomers 23g (K-i = 2.3 nM) and 24g (K-i = 9.6 nM) were active among the carboxylic acid derivatives. The origin of the high affinity of carboxylic acid derivatives such as 18e and 18g would be a charge-charge interaction between the anionic carboxylate residues of the compounds and the cationic proton-donor site in the receptor.