环三癸酮 | 832-10-0

• 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 - 有机氧化合物
• 中文名称: 环三癸酮
• 英文名称: cyclotridecanone
• CAS: 832-10-0
• 化学式: C₁₃H₂₄O
• mdl: MFCD00001265
• 分子量: 196.333
• InChiKey: VHUGWUBIUBBUAF-UHFFFAOYSA-N

物化性质

• 熔点：
  30-31 °C(lit.)
• 沸点：
  146 °C11 mm Hg(lit.)
• 密度：
  0.927 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• LogP：
  4.510 (est)
• 保留指数：
  1647.6;1655;1661.3
• 稳定性/保质期：

  常温常压下稳定，避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.923
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2914299000
• 储存条件：
  密封保存，存放在阴凉干燥的仓库中，并远离氧化剂。

SDS

Name:	Cyclotridecanone tech. Material Safety Data Sheet
Synonym:
CAS:	832-10-0

Section 1 - Chemical Product MSDS Name:Cyclotridecanone tech. Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
832-10-0	Cyclotridecanone, tech.	100	212-615-3

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 immediately.
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:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
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. Water may be ineffective. Material is lighter than water and a fire may be spread by the use of water. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. 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. 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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 832-10-0: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: Colorless Liquid
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 146 deg C @ 11.00mmHg
Freezing/Melting Point: 25 deg C
Autoignition Temperature: Not available.
Flash Point: > 112 deg C (> 233.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: .9270g/cm3
Molecular Formula: C13H24O
Molecular Weight: 196.33

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 832-10-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Cyclotridecanone, tech. - 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
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# 832-10-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 832-10-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 832-10-0 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：

  环三癸酮 在 盐酸羟胺 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 以91%的产率得到Cyclotridecanon-oxim
  参考文献：
  名称：

  细胞毒性海绵生物碱motuporamines A和B的全合成

  摘要：

  The synthesis of two sponge alkaloids, Motuporamines A and B is reported. The key step involved a reductive amination using sodium triacetoxyborohydride. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01016-3
• 作为产物：
  描述：

  cyclotridecyne 在 硫酸 、 mercury(II) sulfate 作用下， 以 1,4-二氧六环 为溶剂， 生成 环三癸酮
  参考文献：
  名称：

  二卤代卡宾TOcistrans,trans-CYCLODODECA-1,5,9-TRIENE的立体选择性加成及环十三酮的合成

  摘要：

  二溴和二氯卡宾与顺式、反式、反式环十二烷-1,5,9-三烯 (I) 的加成反应遵循类似于其他试剂的立体选择性方案，形成三元...

  DOI：

  10.1139/v66-151

文献信息

• New method for generation of β-oxido carbenoid via ligand exchange reaction of sulfoxides: A versatile procedure for one-carbon homologation of carbonyl compounds
  作者：Tsuyoshi Satoh、Norifumi Itoh、Kaoru Gengyo、Sae Takada、Naoyuki Asakawa、Yumi Yamani、Koji Yamakawa

  DOI：10.1016/s0040-4020(01)89299-1

  日期：1994.1

  one-carbon homologation of carbonyl compounds is described. The method is based on the rearrangement of β-oxido carbenoid which is generated via the ligand exchange reaction of the sulfinyl group of α-chloro β-hydroxy sulfoxide with tert-butyllithium. Addition of the carbanion of aryl 1-chloroalkyl sulfoxides to carbonyl compounds gave the adducts in good yields. The β-oxido carbenoid rearrangement of the

  描述了一种新的羰基化合物一碳同系化方法。该方法基于通过α-氯β-羟基亚砜的亚磺酰基与叔丁基锂的配体交换反应而产生的β-氧化类胡萝卜素的重排。将芳基1-氯烷基亚砜的碳负离子加到羰基化合物上，以高收率得到加合物。加合物的β-氧化类胡萝卜素重排得到具有α-烷基取代基的一碳同系羰基化合物。衍生自羰基化合物的加合物与氯甲基对甲苯基亚砜的类似反应产生了亚甲基插入的程序。还讨论了β-氧化类胡萝卜素重排的立体化学。
• Scandium Trifluoromethanesulfonate as an Extremely Active Lewis Acid Catalyst in Acylation of Alcohols with Acid Anhydrides and Mixed Anhydrides
  作者：Kazuaki Ishihara、Manabu Kubota、Hideki Kurihara、Hisashi Yamamoto

  DOI：10.1021/jo952237x

  日期：1996.1.1

  is commercially available, is a practical and useful Lewis acid catalyst for acylation of alcohols with acid anhydrides or the esterification of alcohols by carboxylic acids in the presence of p-nitrobenzoic anhydrides. The remarkably high catalytic activity of scandium triflate can be used for assisting the acylation by acid anhydrides of not only primary alcohols but also sterically-hindered secondary

  可商购的三氟甲磺酸（三氟甲磺酸late）是一种实用且有用的路易斯酸催化剂，用于在对硝基苯甲酸酐的存在下将醇与酸酐酰化或将醇通过羧酸酯化。三氟甲磺酸scan的极高的催化活性可用于协助伯醇的酸酐酰化以及空间受阻的仲或叔醇的酸酐酰化。所提出的方法对于ω-羟基羧酸的选择性大内酯化特别有效。
• A Novel, Short and Repeatable Two-Carbon Ring Expansion Reaction by Thermo-Isomerization: Easy Synthesis of Macrocyclic Ketones
  作者：Matthias Nagel、Hans-Jürgen Hansen、Georg Fráter

  DOI：10.1055/s-2002-19758

  日期：——

  A novel two-carbon ring enlargement procedure, in which medium- and large-ring 1-vinylcycloalkanols are thermoisomerized in a flow reactor system at temperatures of 600 °C to about 650 °C, produces the isomeric ring-expanded cycloalkanones directly and efficiently. This two-step ring expansion protocol can easily be applied several times successively. For e.g., the musk odorant cyclopentadecanone (Exaltone

  一种新型的双碳环扩大程序，其中中环和大环 1-乙烯基环烷醇在流动反应器系统中在 600°C 至约 650°C 的温度下热异构化，直接有效地产生异构环扩大环烷酮。这种两步环扩展协议可以轻松地连续应用多次。例如，麝香气味剂环十五酮 (Exaltone ® ) 是由环十一酮在两个重复循环中制备的。相应的乙炔环烷醇的热异构化产生中等产率的双同源 α,β-不饱和大环 (E)-2- 环烯酮。提出了通过烷基羟基烯丙基双自由基中间体的反应机理。
• A New and Effective Synthetic Method for the Preparation of the Esters, Peptides, and Lactones Using 3-(5-Nitro-2-oxo-1,2-dihydro-1-pyridyl)-1,2-benzisothiazole 1,1-Dioxide. Synthesis of (±)-(<i>E</i>)-8-Dodecen-11-olide, Recifeiolide
  作者：Alauddin Ahmed、Nagahiro Taniguchi、Hirohiko Fukuda、Hideki Kinoshita、Katsuhiko Inomata、Hiroshi Kotake

  DOI：10.1246/bcsj.57.781

  日期：1984.3

  condensing reagent. A variety of esters, dipeptides, and lactones were obtained in excellent yields. Furthermore, BID-NPy was successfully employed for the lactonization step in a new synthesis of a naturally occurring (±)-(E)-8-dodecen-11-olide, recifeiolide.

  3-(5-Nitro-2-oxo-1,2-dihydro-1-pyridyl)-1,2-benziisothiazole 1,1-dioxide(BID-NPy)，很容易从 3-chloro-1,2-benzisothiazole 制备1,1-二氧化物和5-硝基-2-吡啶酮被证明是一种非常有用的缩合剂。以极好的收率获得了多种酯、二肽和内酯。此外，在天然存在的 (±)-(E)-8-dodecen-11-olide、recifeiolide 的新合成中，BID-NPy 成功地用于内酯化步骤。
• Synthese von<i>N</i>-(4-Aminobutyl)-16-aza-19-nonadecanlactam und<i>N</i>-(4-Aminobutyl)-17-aza-20-icosanlactam (Desoxoinandenin)
  作者：Rudolf Wälchli、Armin Giggisberg、Manfred Hesse

  DOI：10.1002/hlca.19840670819

  日期：1984.12.19

  Synthesis of N-(4-Aminobutyl)-16-aza-19-nonadecanelactam and N-(4-Aminobutyl)-17-aza-20-icosanelactam (Desoxoinandenine)

  的合成ñ - （4-氨基丁基）-16-氮杂-19- nonadecanelactam和ñ - （4-氨基丁基）-17-氮杂-20- icosanelactam（Desoxoinandenine）

表征谱图