6-溴-2,2-二甲基-4-二氢色原酮 | 99853-21-1

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 6-溴-2,2-二甲基-4-二氢色原酮
• 中文别名: 4H-1-苯并吡喃-4-酮,6-溴-2,3-二氢-2,2-二甲基
• 英文名称: 6-bromo-2,2-dimethylchroman-4-one
• 英文别名: 6-bromo-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-one；6-bromo-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one；6-bromo-2,2-dimethyl-2,3-dihydro-4H-1-benzopyran-4-one；6-bromo-2,2-dimethyl-3H-chromen-4-one
• CAS: 99853-21-1
• 化学式: C₁₁H₁₁BrO₂
• mdl: MFCD12068434
• 分子量: 255.111
• InChiKey: KMLKUNVLSWKFLA-UHFFFAOYSA-N

物化性质

• 熔点：
  105-106℃
• 沸点：
  332℃
• 密度：
  1.429
• 闪点：
  155℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932999099
• 危险性防范说明：
  P301+P312+P330
• 危险性描述：
  H302
• 储存条件：
  存储条件：2-8℃，干燥，密封保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Bromo-2,2-dimethylchroman-4-one
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-2,2-dimethylchroman-4-one
CAS number: 99853-21-1

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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, refrigerated.
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: C11H11BrO2
Molecular weight: 255.1

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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, 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

反应信息

• 作为反应物：
  描述：

  6-溴-2,2-二甲基-4-二氢色原酮 在 盐酸 、 sodium tetrahydroborate 、 硫酸 作用下， 以 甲醇 为溶剂， 生成 6-溴-3,4-二氢-2,2-二甲基-2H-1-苯并吡喃-4-胺
  参考文献：
  名称：

  4,6-Disubstituted 2,2-Dimethylchromans Structurally Related to the K_ATP Channel Opener Cromakalim: Design, Synthesis, and Effect on Insulin Release and Vascular Tone

  摘要：

  Five series (ureas, thioureas, carbamates, sulfonylureas, and amides) of 4,6-disubstituted-2,2dimethylchromans structurally related to cromakalim were prepared and evaluated, as putative ATP-sensitive potassium channel activators, on rat pancreatic islets and rat aorta rings. The biological data indicate that most compounds were, like the reference molecule cromakalim, more active on the vascular smooth muscle tissue (myorelaxant effect on 30 mM KCl induced contractions of rat aorta rings) than on the pancreatic tissue (inhibition of 16.7 mM glucose induced insulin release from rat pancreatic islets). However, some drugs (8h, 8i, 9f, 9g, 9h, and 9i) markedly inhibited insulin release and exhibited an activity equivalent or greater than that of diazoxide. Compounds 9h and 9i were also found to be more active on pancreatic beta-cells than on vascular smooth muscle cells. Last, the amide 6b was selected in order to examine its mechanism of action on vascular smooth muscle cells. Pharmacological results suggest that the compound acted as a K-ATP channel opener. In conclusion, the present data indicate that appropriate structural modifications can generate dimethylchromans with pharmacological profiles different from that of cromakalim.

  DOI：

  10.1021/jm040789e
• 作为产物：
  描述：

  4-溴苯酚 在 四氢吡咯 、 aluminum (III) chloride 、 硫酸 作用下， 以 甲醇 为溶剂， 生成 6-溴-2,2-二甲基-4-二氢色原酮
  参考文献：
  名称：

  一系列2,2-二甲基苯并二氢吡喃类化合物的结构-活性关系的解密，这些抑制剂可作为胰岛素释放和平滑肌松弛剂的抑制剂

  摘要：

  据报道4,6-二取代的2,2-二甲基苯并二氢吡喃是主要针对ATP敏感钾通道的药理活性化合物。本研究旨在描述在2,2-二甲基苯并吡喃的4和6位上引入的取代基的性质对其抑制胰岛β细胞释放胰岛素或舒张血管平滑肌细胞的能力的影响，这两种生物反应都应该反映与特定离子通道的相互作用。从4-氨基-2,2-二甲基苯并吡喃的核心结构中，在4-位（氨基，甲酰胺基，乙酰胺基，芳基脲基/硫脲基）和6-位（氨基，甲酰胺，乙酰胺，烷氧基羰基氨基）导致对胰岛素释放过程的抑制作用逐步扩大，并且在较小程度上导致血管舒张活性降低。此外，2,2-二甲基苯并二氢吡喃化合物的右旋对映异构体29比左旋对应物对抑制胰岛素分泌过程更有效。然而，另外的药理研究表明，11和15的肌肉松弛药活性是由直接的Ca 2+进入封锁引起的。

  DOI：

  10.1002/cmdc.201700409

文献信息

• Amines substituted with a dihydronaphthalenyl, chromenyl, or thiochromenyl group, an aryl or heteroaryl group and an alkyl group, having retinoid-like biological activity
  申请人：——

  公开号：US20030166932A1

  公开（公告）日：2003-09-04

  Compounds of the formula 1 where the symbols are as defined in the specification, have retinoid agonist, antagonist or negative hormone-like biological activity.

  式中符号如规范中定义，具有视黄醇激动剂、拮抗剂或负激素样生物活性。
• [EN] MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES MACROCYCLIQUES À LARGE SPECTRE
  申请人：RQX PHARMACEUTICALS INC

  公开号：WO2018149419A1

  公开（公告）日：2018-08-23

  Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidase (SpsB), an essential protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.

  本文提供了抗菌化合物，其中在某些实施例中，这些化合物具有广谱生物活性。在各种实施例中，这些化合物通过抑制细菌类型1信号肽酶（SpsB）发挥作用，这是细菌中的一种必需蛋白质。还提供了使用所述化合物的药物组合物和治疗方法。
• Catalytic C–C coupling of diazo compounds with arylboronic acids: using surface modified sewage sludge as catalyst
  作者：Zhipeng Zhang、Yang Yu、Yuxing Xie、Timothy Hughes、Jun Xu、Fei Huang、He Huang

  DOI：10.1039/d0gc00317d

  日期：——

  carbonaceous materials (SW) by perchloric acid catalyzed coupling reactions between diazo compounds and arylboronic acids was developed. The reaction shows a high level of functional tolerance and a broad substrate scope. Furthermore, the highly selective 1,2-alkyl shift products were furnished through the sterically demanding R4, R5 migration of diazo compounds (3-diazochromanone). The structures of 1,2-shift

  通过高氯酸催化重氮化合物与芳基硼酸之间的偶联反应，开发了一种绿色，温和且高效的合成方法，该方法利用污水污泥衍生的碳质材料（SW）合成二芳基次甲基。该反应显示出高水平的功能耐受性和广泛的底物范围。此外，通过空间要求高的R 4，R 5提供了高选择性的1,2-烷基转移产物重氮化合物（3-重氮苯并二氢吡喃酮）的迁移。通过单晶X射线分析进一步证实了1，2-移位产物的结构。值得注意的是，darifenacin（一种用于膀胱过度活动症的临床药物，OAB）和diclofensine（一种显示出抗抑郁和单胺再摄取抑制剂活性的兴奋剂）的核心结构的合成进一步证明了该方法的有效性和合成潜力。
• 3,4,5-Substituted piperidines as therapeutic compounds
  申请人：Herold Peter

  公开号：US20070167433A1

  公开（公告）日：2007-07-19

  Use of compounds of the general formula (I) and pharmaceutically acceptable salt thereof, in which R 1 , R 2 , R 3 , R 4 , W, X and Z, n and m have the definitions illustrated in detail in the description, as beta-secretase, cathepsin D, plasmepsin II and/or HIV protease inhibitors.

  在一般式（I）及其药用可接受盐中使用具有详细定义的R1、R2、R3、R4、W、X和Z、n和m的化合物，作为β-分泌酶、半胱氨酸蛋白酶D、质粒蛋白酶II和/或HIV蛋白酶抑制剂。
• [EN] BENZOTHIAZOLE COMPOUNDS<br/>[FR] COMPOSÉS DE BENZOTHIAZOLE
  申请人：INST MEDICAL W & E HALL

  公开号：WO2009039553A1

  公开（公告）日：2009-04-02

  The present invention relates to benzothiazole compounds that mimic the activity of BH3 only proteins and are capable of binding to and neutralizing pro survival Bcl 2 proteins. The invention also relates to the use of such compounds in the regulation of cell death or cell survival and the treatment and/or prophylaxis of diseases or conditions associated with the deregulation of cell death or cell survival.

  本发明涉及模拟BH3-only蛋白活性并能够结合和中和促生存Bcl-2蛋白的苯并噻唑化合物。该发明还涉及利用这类化合物调节细胞死亡或细胞存活，在治疗和/或预防与细胞死亡或细胞存活失调相关的疾病或病况。