5,5,8,8-四甲基-5,6,7,8-四氢-2-萘甲醛 | 92654-79-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 5,5,8,8-四甲基-5,6,7,8-四氢-2-萘甲醛
• 英文名称: 5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxaldehyde
• 英文别名: 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalene-carboxaldehyde；5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde；5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthalenecarbaldehyde；5,5,8,8-tetramethyl-6,7-dihydronaphthalene-2-carbaldehyde
• CAS: 92654-79-0
• 化学式: C₁₅H₂₀O
• 分子量: 216.323
• InChiKey: RRAGXXOTEICTAF-UHFFFAOYSA-N

物化性质

• 熔点：
  51-53 °C
• 沸点：
  309.6±31.0 °C(Predicted)
• 密度：
  0.962±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2912299000

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5,5,8,8-Tetramethyl-6,7-dihydronaphthalene-2-carbaldehyde
Synonyms: 5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenecarbaldehyde

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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: 5,5,8,8-Tetramethyl-6,7-dihydronaphthalene-2-carbaldehyde
CAS number: 92654-79-0

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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: C15H20O
Molecular weight: 216.3

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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.

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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：

  5,5,8,8-四甲基-5,6,7,8-四氢-2-萘甲醛 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 1.5h， 生成 4-(N-methyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-ylmethylamino)benzoic acid ethyl ester
  参考文献：
  名称：

  Heterocycle-Containing Retinoids. Discovery of a Novel Isoxazole Arotinoid Possessing Potent Apoptotic Activity in Multidrug and Drug-Induced Apoptosis-Resistant Cells

  摘要：

  In a search for retinoic acid (RA) receptor ligands endowed with potent apoptotic activity, a series of novel arotinoids were prepared. Because the stereochemistry of the CS-alkenyl portion of natural 9-cis-RA and the olefinic moiety of the previously synthesized isoxazole retinoid 4 seems to have particular importance for their apoptotic activity, novel retinoid analogues with a restricted or, vice versa, a larger flexibility in this region were designed and prepared. The new compounds were evaluated in vitro for their ability to activate natural retinoid receptors and for their differentiation-inducing activity. Cytotoxic and apoptotic activities were, in addition, evaluated. In general, these analogues showed low cytotoxicity, with the restricted structures being slightly more active than the more flexible ones. As an exception, however, the isoxazole retinoid 15b proved to be particularly able to induce apoptosis at concentrations <5 muM, showing a higher activity than the classical retinoids such as all-trans-RA, 13-cis-RA, and 9-cis-RA and the previously described synthetic retinoid 4. 15b also exhibited a good affinity for the retinoid receptors. Interestingly, another important property of 15b was its ability to induce apoptosis in the HL60R multidrug-resistant (MDR) cell line, at the same concentration as is effective in HL60. Therefore, 15b represents a new retinoid possessing high apoptotic activity in an MDR cell line. The ability of 15b to act on K562 and HL60R cells suggests that this compound may have important implications in the treatment of different leukemias, and its structure could offer an interesting model for the design of new compounds endowed with apoptotic activity on MDR- and retinoid-resistant malignancies.

  DOI：

  10.1021/jm0010320
• 作为产物：
  描述：

  2,5-二氯-2,5-二甲基己烷 在 三氯化铝 、 ammonium cerium(IV) nitrate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 生成 5,5,8,8-四甲基-5,6,7,8-四氢-2-萘甲醛
  参考文献：
  名称：

  Polyenylidene Thiazolidine Derivatives with Retinoidal Activities.

  摘要：

  合成了几种聚烯叉噻唑烷二酮或2-硫代-4-噻唑烷酮衍生物，并通过对人早幼粒细胞白血病HL-60细胞的分化诱导能力和对白细胞介素（IL）-1α诱导的IL-的抑制作用来检测其类视黄醇活性。 MC3T3-E1 细胞中产生 6。含有三甲基环己烯基环的化合物可诱导 HL-60 细胞分化，其活性比视黄酸 (1a) 弱一或两个数量级。噻唑烷二酮衍生物(2,5,7)比相应的2-硫代-4-噻唑烷酮衍生物(3,6,8)表现出更强的活性。类维生素A拮抗剂(LE540)和增效剂(类维生素A X受体(RXR)激动剂，HX600或HX630)对噻唑烷衍生物活性的影响表明这些化合物通过核视黄酸受体(RAR)激发其活性。所有噻唑烷类化合物研究还抑制了 IL-1α 诱导的 IL-6 产生，IC50 值为 10 nM 量级。考虑到用生物等排官能团取代类维生素A结构中的羧酸通常是无效的，噻唑烷的类维生素A活性是显着的，如类维生素A苯甲酸的结构-活性关系中所见。

  DOI：

  10.1248/cpb.45.1805

文献信息

• Efficient Synthesis of New 4-Arylideneimidazolin-5-ones Related to the GFP Chromophore by 2+3 Cyclocondensation of Arylideneimines with Imidate Ylides
  作者：Janusz Kowalik、Anthony Baldridge、Laren Tolbert

  DOI：10.1055/s-0029-1218796

  日期：2010.7

  A 2+3 condensation of a wide assortment of Schiff bases, prepared from aromatic aldehydes and primary amines, with methyl 2-(1-ethoxyethylideneamino)acetate allows convenient access to an extensive family of substituted 4-arylideneimidazolin-5-one analogues of the green fluorescent protein (GFP) chromophore. 4-arylideneimidazolin-5-one - azomethine ylide - Schiff bases - heterocycle - 2+3 cycloaddition

  由芳族醛和伯胺制得的各种席夫碱与2-（1-乙氧基乙叉基氨基）乙酸甲酯的2 + 3缩合反应可方便地获得广泛的取代的4-芳基亚氨基咪唑啉-5-酮类似物家族绿色荧光蛋白（GFP）生色团。 4-芳基亚胺达唑啉-5-酮-甲亚胺叶立德-席夫碱-杂环-2 + 3环加成
• 苯并二氧六环类衍生物、其制备方法及其在医 药上的应用
  申请人：上海恒瑞医药有限公司

  公开号：CN103030646B

  公开（公告）日：2016-08-24

  本发明涉及苯并二氧六环类衍生物、其制备方法及其在医药上的应用。具体而言，本发明涉及一种通式(I)所示的新的苯并二氧六环类衍生物及其可药用的盐或含有其的药物组合物、及其制备方法，本发明进一步涉及所述苯并二氧六环类衍生物及其可药用的盐或含有其的药物组合物在制备治疗剂，特别是GPR40激动剂，和在制备治疗糖尿病和代谢性病症等疾病的药物中的用途，其中通式(I)的各取代基同说明书中的定义相同。
• THERAPEUTIC DRUG FOR ADULT T-CELL LEUKEMIA
  申请人：Baba Masanori

  公开号：US20110172185A1

  公开（公告）日：2011-07-14

  An object is to provide a novel therapeutic drug for adult T-cell leukemia having an ATL cell specific antitumor effect. The therapeutic drug for adult T-cell leukemia according to the invention is characterized by containing a compound represented by the formula I or a prodrug thereof, wherein R 1 is H, OH, an alkoxy group, an acyl group, or a thioacyl group, R 2 is an acyl group, a thioacyl group, CONR 7 R 8 , or CSNR 7 R 8 (R 7 and R 8 being each independently H, an alkyl group containing 1 to 3 carbon atoms, or a phenyl group), or R 1 and R 2 together may form a ring, X 1 and X 2 may be the same or different and are each —CR 3 R 4 —, —SiR 3 R 4 — or oxygen, and R 3 and R 4 may be the same or different and are each an alkyl group containing 1 to 6 carbon atoms.

  一种提供成人T细胞白血病的新型治疗药物的对象是具有ATL细胞特异性抗肿瘤作用。根据本发明的成人T细胞白血病治疗药物的特征在于含有由式I表示的化合物或其前药， 其中R 1 为H、OH、烷氧基、酰基或硫酰基，R 2 为酰基、硫酰基、CONR 7 R 8 或CSNR 7 R 8 （R 7 和R 8 各自独立地为H、含有1至3个碳原子的烷基或苯基），或R 1 和R 2 可共同形成环，X 1 和X 2 可以相同也可以不同，分别为—CR 3 R 4 —、—SiR 3 R 4 —或氧，R 3 和R 4 可以相同也可以不同，分别为含有1至6个碳原子的烷基。
• Novel tetrahydronaphthalene and indane derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US04870219A1

  公开（公告）日：1989-09-26

  Novel styryl-tetrahydromaphythalene and indane derivatives useful for treating neoplasms and dermatoses.

  新型苯基四氢萘和茚衍生物可用于治疗肿瘤和皮肤病。
• Aromatic keto compounds, the preparation thereof, and drugs and
  申请人：BASF Aktiengesellschaft

  公开号：US05194664A1

  公开（公告）日：1993-03-16

  Compounds of the general formula I ##STR1##

  通式I的化合物