6-溴-1,2,3,4-四氢-4,4-二甲基喹啉盐酸盐 | 135631-91-3

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 6-溴-1,2,3,4-四氢-4,4-二甲基喹啉盐酸盐
• 中文别名: 6-溴-1,2,3,4-四氢-4,4-二甲基喹啉
• 英文名称: 6-bromo-4,4-dimethyl-1,2,3,4-tetrahydroquinoline
• 英文别名: 6-bromo-4,4-dimethyl-2,3-dihydro-1H-quinoline
• CAS: 135631-91-3
• 化学式: C₁₁H₁₄BrN
• 分子量: 240.143
• InChiKey: WBOOAXJWGJAIMB-UHFFFAOYSA-N

物化性质

• 沸点：
  304.9±41.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

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: 6-Bromo-4,4-dimethyl-1,2,3,4-tetrahydroquinoline, 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: 6-Bromo-4,4-dimethyl-1,2,3,4-tetrahydroquinoline, HCl
CAS number: 135631-91-3

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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: C11H15BrClN
Molecular weight: 276.6

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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, hydrogen bromide.

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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

制备方法与用途

6-溴-1,2,3,4-四氢-4,4-二甲基喹啉盐酸盐是一种杂环化合物，可用作医药合成中间体。

如不慎吸入该物质，请将患者移至空气新鲜处；若皮肤接触，应立即脱去污染衣物，并用肥皂水和清水彻底清洗皮肤，如有不适，请及时就医；眼睛接触到该物质时，应翻开眼睑，用流动清水或生理盐水冲洗，并尽快就医；如果误食，应立即漱口，禁止催吐，并迅速就医。

反应信息

• 作为反应物：
  描述：

  6-溴-1,2,3,4-四氢-4,4-二甲基喹啉盐酸盐 以 甲酸 为溶剂， 反应 3.0h， 以90%的产率得到6-溴-4,4-二甲基-1,2,3,4-四氢-喹啉-1-甲醛
  参考文献：
  名称：

  Compounds having activity as inhibitors of cytochrome P450RAI

  摘要：

  具有Formula 8的化合物，在其中符号的含义已在说明书中定义，是细胞色素P450RAI（维甲酸诱导）酶的抑制剂，用于治疗对维甲酸类药物治疗有响应的疾病。

  公开号：

  US06369225B1
• 作为产物：
  描述：

  3-甲基巴豆酰氯 在 aluminum (III) chloride 、 dimethyl sulfide borane 作用下， 以 氯仿 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 9.0h， 生成 6-溴-1,2,3,4-四氢-4,4-二甲基喹啉盐酸盐
  参考文献：
  名称：

  柔性杂芳烃类化合物（Flex-Hets）中的四氢喹啉单元在A2780卵巢癌细胞中具有抗癌特性。

  摘要：

  SHetA2（NSC 721689）是我们的领先Flex-Het抗癌药，由硫代色烷（A环）和4-硝基苯基（B环）通过硫脲桥连接而成。在这项工作中，已经制备了一系列新的类似物，它们具有通过尿素或硫脲接头与4-取代的苯基（环B）连接的四氢喹啉（THQ，环A）单元，并相对于SHetA2进行了结合亲和力评估。 mortalin和抑制A2780卵巢癌细胞。六种衍生物等于或超过了SHetA2所示的功效。化合物1a-d（系列1）在A环氮原子上缺少甲基，而在相邻碳原子上缺少宝石-二甲基，则仅显示出较弱的活性。盐2，1a的季铵化N，N-二甲基碘盐类似物，在所研究的细胞系中也具有非常适度的生长抑制作用。系列3化合物 碳原子数为3的酮和N-甲基取代了环A中的硫的化合物最为成功。化合物3a [环A ＝ 1,2,2,4,4-五甲基-3-氧代-1,2,3,4-四氢喹啉-6-基；尿素接头; B环= 4-硝基苯基]的效能（IC50

  DOI：

  10.1016/j.bmc.2019.115244

文献信息

• 5-[phenyl-tetrahydronaphthalene-2-yl dihydronaphthalen-2-yl and heteroaryl-cyclopropyl]-pentadienoic acid derivatives having serum glucose reducing activity
  申请人：Sinha Santosh

  公开号：US20050004213A1

  公开（公告）日：2005-01-06

  Compounds of the formula where the variables have the meaning defined in the specification are capable of reducing serum glucose levels in diabetic mammals without the undesirable side effects of reducing serum thyroxine levels and transiently increasing triglyceride levels.

  式中变量的含义如规范中定义的那样，这些化合物能够降低糖尿病哺乳动物的血清葡萄糖水平，而不会出现降低血清甲状腺素水平和短暂增加甘油三酯水平的不良副作用。
• Disubstituted acetylenes bearing heteroaromatic and heterobicyclic
  申请人：Allergan

  公开号：US05602130A1

  公开（公告）日：1997-02-11

  Retinoid-like activity is exhibited by compounds of the formula ##STR1## where X is S, O, or NR' where R' is hydrogen or lower alkyl; R is hydrogen or lower alkyl; A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-4; and B is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative, or --CHO or an acetal derivative, or --COR.sub.1 or a ketal derivative where R.sub.1 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4, or a pharmaceutically acceptable salt thereof.

  化合物具有类似视黄醇的活性，其化学式为##STR1##其中X为S、O或NR'，R'为氢或较低的烷基；R为氢或较低的烷基；A为吡啶基、噻吩基、呋喃基、吡啶并嗪基、嘧啶基或吡嗪基；n为0-4；B为H、--COOH或其药学上可接受的盐、酯或酰胺，--CH.sub.2 OH或醚或酯衍生物，或--CHO或缩醛衍生物，或--COR.sub.1或缩酮衍生物，其中R.sub.1为--(CH.sub.2).sub.m CH.sub.3，m为0-4，或其药学上可接受的盐。
• Methods of providing and using compounds having activity as inhibitors of cytochrome P450RAI
  申请人：Allergan Sales, Inc.

  公开号：US06313107B1

  公开（公告）日：2001-11-06

  Novel compounds having the Formulas 1 through 8, wherein the symbols have the meaning defined in the specification, and certain previously known compounds have been discovered to act as inhibitors of the cytochrome P450RAI (retinoic acid inducible) enzyme, and are used for treating diseases responsive to treatment by retinoids. The compound can also be used in co-treatment with retinoids.

  具有1至8号式的新化合物，其中符号的含义在说明书中有定义，并且已发现某些先前已知的化合物可作为细胞色素P450RAI（诱导性维生素A酸）酶的抑制剂，并用于治疗对维生素A酸治疗产生响应的疾病。该化合物还可与维生素A酸一起进行联合治疗。
• CHROMAN-SUBSTITUTED, TETRAHYDROQUINOLINE-SUBSTITUTED AND THIOCHROMAN-SUBSTITUTED HETEROAROTINOIDS AS ANTI-CANCER AGENTS
  申请人：THE BOARD OF REGENTS FOR OKLAHOMA STATE UNIVERSITY

  公开号：US20200062711A1

  公开（公告）日：2020-02-27

  Chemical compounds that inhibit cancer cell growth are provided. The compounds are heteroarotinoids and derivatives thereof with oxygen, nitrogen or sulfur in chroman systems, tetrahydroquinoline systems, and tetrahydrothiochroman systems.

  提供了抑制癌细胞生长的化合物。这些化合物是杂环维生素A类化合物及其衍生物，其在色酮系统、四氢喹啉系统和四氢硫色酮系统中含有氧、氮或硫。
• Tetrahydroquinoline units in flexible heteroarotinoids (Flex-Hets) convey anti-cancer properties in A2780 ovarian cancer cells
  作者：Krishna Kumar Gnanasekaran、Tim Pouland、Richard A. Bunce、K. Darrell Berlin、Suaad Abuskhuna、Dipendra Bhandari、Maryam Mashayekhi、Donghua H. Zhou、Doris M. Benbrook

  DOI：10.1016/j.bmc.2019.115244

  日期：2020.1

  the derivatives equaled or exceeded the efficacy shown by SHetA2. Compounds 1a-d (series 1), lacking a methyl on the Ring A nitrogen and the gem-dimethyls on the adjacent carbon, showed only weak activity. Salt 2, the quaternized N,N-dimethyl iodide salt analog of 1a, also possessed very modest growth inhibition in the cell line studied. Series 3 compounds, which had a C3 ketone and an N-methyl replacing

  SHetA2（NSC 721689）是我们的领先Flex-Het抗癌药，由硫代色烷（A环）和4-硝基苯基（B环）通过硫脲桥连接而成。在这项工作中，已经制备了一系列新的类似物，它们具有通过尿素或硫脲接头与4-取代的苯基（环B）连接的四氢喹啉（THQ，环A）单元，并相对于SHetA2进行了结合亲和力评估。 mortalin和抑制A2780卵巢癌细胞。六种衍生物等于或超过了SHetA2所示的功效。化合物1a-d（系列1）在A环氮原子上缺少甲基，而在相邻碳原子上缺少宝石-二甲基，则仅显示出较弱的活性。盐2，1a的季铵化N，N-二甲基碘盐类似物，在所研究的细胞系中也具有非常适度的生长抑制作用。系列3化合物 碳原子数为3的酮和N-甲基取代了环A中的硫的化合物最为成功。化合物3a [环A ＝ 1,2,2,4,4-五甲基-3-氧代-1,2,3,4-四氢喹啉-6-基；尿素接头; B环= 4-硝基苯基]的效能（IC50