四酮-1-肟 | 3349-64-2

• 物质功能分类: 化学试剂 - 有机试剂 - 肟
• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 四酮-1-肟
• 中文别名: 3,4-二氢-1(2H)-萘酮肟
• 英文名称: 1-tetralone oxime
• 英文别名: 3,4-dihydronaphthalen-1(2H)-one oxime；tetralone oxime；3,4-dihydro-2H-naphthalen-1-one oxime；benzocyclohexanone oxime；N-(3,4-dihydro-2H-naphthalen-1-ylidene)hydroxylamine
• CAS: 3349-64-2
• 化学式: C₁₀H₁₁NO
• mdl: MFCD00029228
• 分子量: 161.203
• InChiKey: YFDVQUUMKXZPLK-UHFFFAOYSA-N

物化性质

• 熔点：
  103 °C
• 沸点：
  318.6±12.0 °C(Predicted)
• 密度：
  1.16

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2928000090
• 储存条件：
  2-8°C

SDS

Name:	1 2 3 4-Tetrahydronaphthalen-1-one oxime 97% Material Safety Data Sheet
Synonym:
CAS:	3349-64-2

Section 1 - Chemical Product MSDS Name:1 2 3 4-Tetrahydronaphthalen-1-one oxime 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3349-64-2	1,2,3,4-Tetrahydronaphthalen-1-one oxi	97%	222-106-8

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause 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.
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 water spray, dry chemical, carbon dioxide, or chemical 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.

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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.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 3349-64-2: 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: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 103 - 105 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: C10H11NO
Molecular Weight: 161

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Reducing agents, strong oxidizing agents, acid chlorides.
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# 3349-64-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1,2,3,4-Tetrahydronaphthalen-1-one oxime - 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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 3349-64-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 3349-64-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3349-64-2 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：

  四酮-1-肟 在 sodium 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 丙醇 、 乙腈 为溶剂， 反应 4.0h， 生成 1-isothiocyanato-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Synthesis of tetrahydronaphthyl thioureas as potent appetite suppressants☆

  摘要：

  A series of thiourea derivatives (7-23, 25-27) of 1-aminotetrahydronaphthalene (4) and 1-amino-2-hydroxytetrahydronaphthalene (5) were synthesized in single pot in 48-90% yield and evaluated for their anorexigenic activity. Among them compounds 10, 14 15, 16 and 22 exhibited significant anorexigenic activity without any antidepressant effect and provided a new structural lead for appetite suppressants. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.039
• 作为产物：
  描述：

  3,4-二氢-1(2H)-萘酮 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以99%的产率得到四酮-1-肟
  参考文献：
  名称：

  新型醛酮还原酶 1C3 抑制剂作为癌症耐药性化疗增效剂的发现

  摘要：

  作为在多种癌症中过度表达的关键靶标，醛酮还原酶 1C3 (AKR1C3) 赋予许多临床药物化疗耐药性。然而，应用于临床的 AKR1C3 选择性抑制剂数量有限，这表明鉴定活性化合物的重要性。在此，我们报告了具有结构多样性的新型有效 AKR1C3 抑制剂的发现、合成和评估。这些活性化合物的分子动力学模拟为解释的生物学数据提供了合理的澄清。此外，我们证明 AKR1C3 抑制剂有可能成为使耐药细胞系对化疗重新敏感的优质治疗药物，特别是泛 AKR1C 抑制剂S07-2010。我们的研究鉴定了AKR1C3抑制剂的新结构类别，丰富了结构多样性，有利于未来抑制剂的合理设计和结构优化。此外，这些化合物可以作为对抗耐药性的新疗法的有前途的治疗佐剂。

  DOI：

  10.1021/acsmedchemlett.2c00175
• 作为试剂：
  描述：

  N-(3-氨丙基)吗啉 、 4-溴苄醇 在 copper(l) iodide 、 四酮-1-肟 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 36.0h， 以87%的产率得到4-(3-morpholinopropylamino)-benzyl alcohol
  参考文献：
  名称：

  净水中室温铜催化脂肪胺的N-芳基化

  摘要：

  已开发出室温和无PTC的纯水中脂族胺的N-芳基化反应的铜。使用CuI和6,7-二氢喹啉-8（5 H）-一种肟作为催化剂，并用KOH作为碱，多种脂族胺被各种芳基和杂芳基卤化物芳基化，得到相应的产物达到95％的收率。

  DOI：

  10.1039/c7ob02126g

文献信息

• Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20150231142A1

  公开（公告）日：2015-08-20

  The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

  本发明涉及含有上皮钠通道活性抑制剂与至少一种ABC转运蛋白调节剂化合物（A式、B式、C式或D式）的药物组合物。该发明还涉及这些药物配方，以及使用这些组合物治疗CFTR介导的疾病，特别是囊性纤维化的方法。
• Iron-Catalyzed Synthesis of 2<i>H</i>-Imidazoles from Oxime Acetates and Vinyl Azides under Redox-Neutral Conditions
  作者：Zhongzhi Zhu、Xiaodong Tang、Jianxiao Li、Xianwei Li、Wanqing Wu、Guohua Deng、Huanfeng Jiang

  DOI：10.1021/acs.orglett.7b00203

  日期：2017.3.17

  A novel and versatile method for the synthesis of 2H-imidazoles via iron-catalyzed [3 + 2] annulation from readily available oxime acetates with vinyl azides has been developed. This denitrogenative process involved N–O/N–N bond cleavages and two C–N bond formations to furnish 2,4-substituted 2H-imidazoles. This protocol was performed under mild reaction conditions and needed no additives or ligands

  已开发出一种新颖且通用的方法，该方法通过铁催化的[3 + 2]环合反应从易于获得的肟肟与叠氮化乙烯中合成2 H-咪唑。该脱氮过程涉及N–O / N–N键断裂和两个C–N键形成，以提供2,4-取代的2 H-咪唑。该方案在温和的反应条件下进行，不需要添加剂或配体。此外，这是绿色反应，涉及乙酸肟肟作为内部氧化剂，乙酸和氮作为副产物。
• SO₂ F₂ -Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams
  作者：Guofu Zhang、Yiyong Zhao、Lidi Xuan、Chengrong Ding

  DOI：10.1002/ejoc.201900844

  日期：2019.8.15

  A novel protocol for the efficient activation of the Beckmann rearrangement utilizing the readily available sulfuryl fluoride (SO2F2 gas) is reported. The substrate scope of this methodology has been demonstrated by 37 examples with good to nearly quantitative isolated yields in a short time. A tentative mechanism was proposed involving formation and elimination of sulfonyl ester.

  报道了一种利用容易获得的硫酰氟（SO 2 F 2气体）有效激活贝克曼重排的新方案。该方法的底物范围已通过37个实例证明，并在短时间内获得了良好至近乎定量的分离产率。提出了一种尝试性的机制，涉及形成和消除磺酰基酯。
• Synthesis of Air- and Moisture-Stable, Storable Chiral Oxorhenium Complexes and Their Application as Catalysts for the Enantioselective Imine Reduction
  作者：Braja Gopal Das、Rajender Nallagonda、Dhananjay Dey、Prasanta Ghorai

  DOI：10.1002/chem.201501914

  日期：2015.9.1

  salicyloxazoline based oxorhenium(V) complexes have been synthesized and their catalytic application for the asymmetric reduction of ketimines using hydrosilane as hydride source is disclosed. A broad substrate scope, high yields, and excellent enantioselectivities (up to 99 %) are attained. Furthermore, the syntheses of enantiopure α‐amino esters, γ‐ and δ‐lactams, and isoindolinones have also been carried

  合成了空气/水分稳定，晶体和可储存的手性水杨基恶唑啉基氧化（V）配合物，并公开了其在氢化硅烷作为氢化物源的情况下催化不对称还原酮亚胺的催化应用。获得了广泛的底物范围，高收率和出色的对映选择性（最高99％）。此外，对映体纯α-氨基酯，γ-和δ-内酰胺以及异吲哚啉酮的合成也已使用该方法进行。最后，该方法已应用于具有药物相关性的合成靶标，例如R -（+）-沙丁胺碱和R -（+）-crispine A.
• Copper-catalyzed synthesis of thiazol-2-yl ethers from oxime acetates and xanthates under redox-neutral conditions
  作者：Zhongzhi Zhu、Xiaodong Tang、Jinghe Cen、Jianxiao Li、Wanqing Wu、Huanfeng Jiang

  DOI：10.1039/c8cc00445e

  日期：——

  acetates and xanthates for the synthesis of thiazol-2-yl ethers with remarkable regioselectivity has been developed. Various oxime acetates, whether derived from aryl ketones or alkyl ketones, or natural product cores are suitable for this conversion. Unique dihydrothiazoles were also obtained when both reaction sites were methine. Mechanistic studies indicated that imino copper(III) intermediates were involved

  新型的铜催化的肟肟酸酯和黄药酸酯的环化反应用于合成噻唑-2-基醚，具有显着的区域选择性。各种衍生自芳基酮或烷基酮的乙酸肟酯，或天然产物核均适用于该转化。当两个反应位点均为次甲基时，也获得了独特的二氢噻唑。机理研究表明，涉及亚氨基铜（III）中间体。另外，该方案在氧化还原中性条件下进行，不需要添加剂或配体。