10,11-二氢二苯并[a,b]环庚烯-5-酮 | 1210-35-1

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 中文名称: 10,11-二氢二苯并[a,b]环庚烯-5-酮
• 中文别名: 二苯并[A,A]环庚-5-酮；10,11-二氢二苯并[a,d]环庚烯-5-酮；二苯并[A,D]环庚二烯酮-(5)；二苯并软木酮；二苯并环庚烯酮；二苯并环庚酮；二苯并环庚酮(DBS)；二苯并[a,d]环庚二烯酮-(5)；二苯并[a,a]环庚-5-酮
• 英文名称: 10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-one
• 英文别名: dibenzosuberone；10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-one；tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaen-2-one
• CAS: 1210-35-1
• 化学式: C₁₅H₁₂O
• mdl: MFCD00003587
• 分子量: 208.26
• InChiKey: BMVWCPGVLSILMU-UHFFFAOYSA-N

物化性质

• 熔点：
  32-34 °C(lit.)
• 沸点：
  148 °C0.3 mm Hg(lit.)
• 密度：
  1.156 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• 溶解度：
  0.03g/l
• LogP：
  3.855 (est)
• 稳定性/保质期：
  如果按照规格使用和储存，一般不会分解，并且没有已知的危险反应。需要注意避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  29143900
• 危险品运输编号：
  200kgs
• RTECS号：
  HP1149700
• 危险性防范说明：
  P264,P264,P280,P302+P352,P337+P313,P362+P364,P332+P313
• 危险性描述：
  H315,H319
• 储存条件：
  保持贮藏器密封，并将其存放在阴凉、干燥处。确保工作间有良好的通风或排气装置。

SDS

Name:	Dibenzosuberone 97% Material Safety Data Sheet
Synonym:	Dibenzocycloheptadienone; 10,11-Dihydro-5H-Dibenzo[A,D]Cyclohepten-5-One
CAS:	1210-35-1

Section 1 - Chemical Product MSDS Name:Dibenzosuberone 97% Material Safety Data Sheet
Synonym:Dibenzocycloheptadienone; 10,11-Dihydro-5H-Dibenzo[A,D]Cyclohepten-5-One

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1210-35-1	Dibenzosuberone	97.0%	214-912-3

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or 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:

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam. Use agent most appropriate to extinguish fire.

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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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 1210-35-1: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 148 deg C @ .30mmHg
Freezing/Melting Point: 32.00 - 34.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: > 112 deg C (> 233.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: insoluble
Specific Gravity/Density: 1.1560g/cm3
Molecular Formula: C15H12O
Molecular Weight: 208.26

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1210-35-1: HP1149700 LD50/LC50:
CAS# 1210-35-1: Draize test, rabbit, eye: 100 mg Moderate; Oral, mouse: LD50 = 1800 uL/kg.
Carcinogenicity:
Dibenzosuberone - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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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.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 1210-35-1: No information available.
Canada
CAS# 1210-35-1 is listed on Canada's DSL List.
CAS# 1210-35-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1210-35-1 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质：熔点为32-34℃，沸点148℃（40Pa），相对密度1.156，折光率1.6332。

用途：主要用于合成医药中间体阿米替林。

生产方法：由邻β-苯乙基苯甲酸经环合而得。

反应信息

• 作为反应物：
  描述：

  10,11-二氢二苯并[a,b]环庚烯-5-酮 在 甲醇 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 20.0~200.0 ℃ 、11.0 MPa 条件下， 反应 0.01h， 生成 阿米替林
  参考文献：
  名称：

  阿米替林连续流合成中的多种有机锂生成

  摘要：

  AbstractA continuous flow protocol for the preparation of the tricyclic antidepressant (TCA) amitriptyline is reported. The advantages of flow chemistry when handling organometallic agents as well as when performing reaction with gases are demonstrated. Continuous multilithiation combined with carboxylation and the Parham cyclization, a Grignard addition and thermolytic water elimination by inductive heating are key features of the multistep protocol.magnified image

  DOI：

  10.1002/adsc.201300614
• 作为产物：
  描述：

  盐酸阿米替林 在 potassium permanganate 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 10,11-二氢二苯并[a,b]环庚烯-5-酮
  参考文献：
  名称：

  SPECTROPHOTOMETRIC DETERMINATION OF AMITRIPTYLINE HCl IN PURE AND PHARMACEUTICAL FORMS

  摘要：

  DOI：

  10.4067/s0717-97072014000100005

文献信息

• Neutral Dinuclear Copper(I)-NHC Complexes: Synthesis and Application in the Hydrosilylation of Ketones
  作者：Michael Trose、Faïma Lazreg、Tao Chang、Fady Nahra、David B. Cordes、Alexandra M. Z. Slawin、Catherine S. J. Cazin

  DOI：10.1021/acscatal.6b02723

  日期：2017.1.6

  The synthesis of a class of highly stable neutral dinuclear Cu(I)-NHC complexes using 1,2,4-triazole as a bridging ligand is described. Various NHCs were used to generate a library of [Cu(μ-trz)(NHC)]2 complexes. Interestingly, [Cu(μ-trz)(IPr)]2 was found to be highly active in the hydrosilylation of ketones, without the need for an external base or any other additive. A wide range of aryl and alkyl

  描述了使用1,2,4-三唑作为桥连配体的一类高度稳定的中性双核Cu（I）-NHC配合物的合成。各种NHC用于生成[Cu（μ-trz）（NHC）] 2配合物的库。有趣的是，发现[Cu（μ-trz）（IPr）] 2在酮的氢化硅烷化中具有很高的活性，而无需外部碱或任何其他添加剂。使用迄今报道的最低催化剂负载量，已成功将各种芳基和烷基酮以及位阻酮成功还原为醇。
• Facile Protocol for Catalytic Frustrated Lewis Pair Hydrogenation and Reductive Deoxygenation of Ketones and Aldehydes
  作者：Tayseer Mahdi、Douglas W. Stephan

  DOI：10.1002/anie.201503087

  日期：2015.7.13

  A series of ketones and aldehydes are reduced in toluene under H2 in the presence of 5 mol % B(C6F5)3 and either cyclodextrin or molecular sieves affording a facile metal‐free protocol for reduction to alcohols. Similar treatment of aryl ketones resulted in metal‐free deoxygenation yielding aromatic hydrocarbons.

  在H 2下，在5 mol％B（C 6 F 5）3的存在下，一系列甲苯中的酮和醛被还原，环糊精或分子筛提供了一种简便的无金属还原醇的方案。芳基酮的类似处理导致无金属脱氧，生成芳烃。
• [EN] OXIME ESTER PHOTOINITIATORS<br/>[FR] PHOTO-INITIATEURS À BASE D'ESTER D'OXIME
  申请人：BASF SE

  公开号：WO2021175855A1

  公开（公告）日：2021-09-10

  Disclosed are α-oxo oxime ester compounds based on carbazole derivatives which have specific substituent groups useful as a photoinitiator, as well as photopolymerizable compositions comprising said photoinitiator and ethylenically unsaturated compounds. The photopolymerizable compositions are useful, for example, in photoresist formulations for display applications, e.g. liquid crystal display (LCD), organic light emitting diode (OLED) and touch panel.

  揭示了基于咔唑衍生物的α-氧代肟酯化合物，其具有特定取代基，可用作光引发剂，以及包括所述光引发剂和乙烯不饱和化合物的光聚合组合物。这些光聚合组合物可用于例如显示应用的光阻配方，例如液晶显示器（LCD）、有机发光二极管（OLED）和触摸面板。
• Dual Ligand-Enabled Late-Stage Fujiwara–Moritani Reactions
  作者：Manuel van Gemmeren、Carlos Santiago、Hao Chen、Arup Mondal

  DOI：10.1055/s-0040-1706014

  日期：2022.3

  for the late-stage olefination of arenes. Building upon a method previously developed for simple arenes, a variety of complex arene substrates were functionalized. Importantly, the method uses the arene as a limiting reactant and is therefore suitable for valuable starting materials that cannot be used in excess. The regioselectivity of the transformation is controlled by the steric and electronic properties

  在这项研究中，我们描述了基于双配体的钯催化剂用于芳烃的后期烯烃化。在以前为简单的芳烃开发的方法的基础上，对各种复杂的芳烃底物进行了功能化。重要的是，该方法使用芳烃作为限制反应物，因此适用于不能过量使用的有价值的原料。转化的区域选择性由底物的空间和电子性质控制，提供了对区域异构体的访问，这对于通过其他合成方法制备将具有挑战性。
• Photochemical C–F Activation Enables Defluorinative Alkylation of Trifluoroacetates and -Acetamides
  作者：Mark W. Campbell、Viktor C. Polites、Shivani Patel、Juliette E. Lipson、Jadab Majhi、Gary A. Molander

  DOI：10.1021/jacs.1c11059

  日期：2021.12.1

  commodity feedstock: ethyl trifluoroacetate. A novel mechanistic approach was identified using our previously developed diaryl ketone HAT catalyst to enable the hydroalkylation of a diverse suite of alkenes. Furthermore, electrochemical studies revealed that more challenging radical precursors, namely trifluoroacetamides, could also be functionalized via synergistic Lewis acid/photochemical activation

  尽管宝石-二氟亚甲基具有诱人的结构、物理和生化特性，但将其安装到有机结构中仍然是一项艰巨的合成挑战。一种非常有效的逆合成方法是将来自三氟甲基的单个 C-F 键功能化。这一系列攻击的最新进展使三氟甲基芳烃的 C-F 活化成为可能，但将可访问的基序限制为仅苄基宝石-二氟化支架。相比之下，三氟乙酸盐的 C-F 活化将使它们能够用作双功能宝石-二氟亚甲基合成子。在此，我们报告了一种光化学介导的商品原料脱氟烷基化方法：三氟乙酸乙酯。使用我们之前开发的二芳基酮 HAT 催化剂确定了一种新的机制方法，以实现多种烯烃的加氢烷基化。此外，电化学研究表明，更具挑战性的自由基前体，即三氟乙酰胺，也可以通过协同路易斯酸/光化学活化进行功能化。最后，该方法为 FDA 批准的药物化合物的新型宝石-二氟类似物提供了一种简洁的合成方法。

表征谱图