蒎酮酸 | 473-72-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 蒎酮酸
• 英文名称: pinonic acid
• 英文别名: Pinonsaeure；2-(3-acetyl-2,2-dimethylcyclobutyl)acetic acid
• CAS: 473-72-3
• 化学式: C₁₀H₁₆O₃
• mdl: MFCD00066726
• 分子量: 184.235
• InChiKey: SIZDUQQDBXJXLQ-UHFFFAOYSA-N

物化性质

• 熔点：
  104～107℃
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38

SDS

Name:	cis-Pinonic acid 98% Material Safety Data Sheet
Synonym:	cis-3-Acetyl-2,2-dimethylcyclobutaneacetic aci
CAS:	473-72-3

Section 1 - Chemical Product MSDS Name:cis-Pinonic acid 98% Material Safety Data Sheet
Synonym:cis-3-Acetyl-2,2-dimethylcyclobutaneacetic aci

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
473-72-3	cis-Pinonic acid, 98%	98%	207-471-3

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
Causes gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation.
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:
Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. Get medical aid if cough or other symptoms appear.
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.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

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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:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower.
Exposure Limits CAS# 473-72-3: Personal Protective Equipment Eyes: Wear chemical splash goggles.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear a chemical apron.
Respirators:
A NIOSH/MSHA approved air purifying dust or mist respirator or European Standard EN 149.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white to pale yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 104 - 107 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: C10H16O3
Molecular Weight: 184.23

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Not available.
Incompatibilities with Other Materials:
Strong 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# 473-72-3: GU0200000 LD50/LC50:
Not available.
Carcinogenicity:
cis-Pinonic acid, 98% - 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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 473-72-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 473-72-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 473-72-3 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：

  蒎酮酸 在 氢氧化钾 、 silver nitrate 作用下， 以 乙醚 为溶剂， 生成 3-(3-Acetyl-2,2-dimethyl-cyclobutyl)-propionic acid methyl ester
  参考文献：
  名称：

  Meikle,P.I.; Whittaker,D., Journal of the Chemical Society. Perkin transactions II, 1974, p. 318 - 321

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(3-乙酰基-2,2-二甲基环丁基)乙醛 在 氢氧化钾 、 乙醇 、 氧气 作用下， 生成 蒎酮酸
  参考文献：
  名称：

  溶液中亚硝基衍生物的光化学—XXX：温度对萜烯自由基加成反应和2-铵亚硝基链烷烃反应的影响

  摘要：

  研究了温度对铝自由基引发的光致加成反应的三个单萜的影响。N-亚硝基哌啶与樟脑和松烯的光加成反应，得到了α-哌啶叔亚硝基链烷烃，是由1,2-加成反应生成的主要加合物。烯的添加需要低温（−40°）才能抑制C自由基中间体的环丁烷开环途径。由于这些α-哌啶亚硝基链烷烃的官能团可呈现顺式-共面构型，因此它们容易发生裂解反应，得到相应的肟和铵盐。随着光解温度的升高，除松油外，环丁烷开环途径逐渐主导了反应，从而增加了8-亚硝基-p的含量。进行溶剂分解和消除反应的-薄荷烯衍生物。提出了一种机械解释，该解释支持C-自由基中间体的均相开环过程。结果建立了逐步添加到烯烃的诊断规则。追加了从商业sample烯样品中高效制备三环素的方法。

  DOI：

  10.1016/0040-4020(75)80237-7

文献信息

• Identification and Quantification of Aerosol Polar Oxygenated Compounds Bearing Carboxylic or Hydroxyl Groups. 1. Method Development
  作者：M. Jaoui、T. E. Kleindienst、M. Lewandowski、E. O. Edney

  DOI：10.1021/ac049919h

  日期：2004.8.1

  In this study, a new analytical technique was developed for the identification and quantification of multifunctional compounds containing simultaneously at least one hydroxyl or one carboxylic group, or both. This technique is based on derivatizing first the carboxylic group(s) of the multifunctional compound using an alcohol (e.g., methanol, 1-butanol) in the presence of a relatively strong Lewis acid (BF3) as a catalyst. This esterification reaction quickly and quantitatively converts carboxylic acids to their ester forms. The second step is based on silylation of the ester compounds using bis(trimethylsilyl) trifluoroacetamide (BSTFA) as the derivatizing agent. For compounds bearing ketone groups in addition to carboxylic and hydroxyl groups, a third step was used based on PFBHA derivatization of the carbonyls. Different parameters including temperature, reaction time, and effect due to artifacts were optimized. A GC/MS in EI and in methane-CI mode was used for the analysis of these compounds. The new approach was tested on a number of multifunctional compounds. The interpretation of their EI (70 eV) and CI mass spectra shows that critical information is gained leading to unambiguous identification of unknown compounds. For example, when derivatized only with BF3−methanol, their mass spectra comprise primary ions at m/z M•+ + 1, M•+ + 29, and M•+ − 31 for compounds bearing only carboxylic groups and M•+ + 1, M•+ + 29, M•+ − 31, and M+. − 17 for those bearing hydroxyl and carboxylic groups. However, when a second derivatization (BSTFA) was used, compounds bearing hydroxyl and carboxylic groups simultaneously show, in addition to the ions observed before, ions at m/z M•+ + 73, M•+ − 15, M•+ − 59, M•+ − 75, M•+ − 89, and 73. To the best of our knowledge, this technique describes systematically for the first time a method for identifying multifunctional oxygenated compounds containing simultaneously one or more hydroxyl and carboxylic acid groups.

  在本研究中，开发了一种新的分析技术，用于鉴定和定量含有至少一个羟基或一个羧基或两者的多官能团化合物。该技术基于首先使用醇（例如甲醇、1-丁醇）在相对较强的路易斯酸（BF3）催化下对多官能团化合物的羧基进行衍生化。这种酯化反应迅速且定量地将羧酸转化为酯形式。第二步是使用双(三甲基硅基)三氟乙酰胺（BSTFA）作为衍生化剂对酯化合物进行硅烷化。对于除羧基和羟基外还含有酮基的化合物，采用了基于PFBHA对羰基进行衍生化的第三步。优化了包括温度、反应时间和因人工产物引起的影响等多个参数。使用电子轰击源（EI）和甲烷化学电离（CI）模式的气相色谱/质谱法（GC/MS）分析了这些化合物。对多种多官能团化合物测试了新方法。对其EI（70 eV）和CI质谱的解释表明，获得了关键信息，从而能够明确鉴定未知化合物。例如，仅通过BF3−甲醇衍生化时，它们的质谱包含仅含有羧基的化合物的离子m/z M•+ + 1、M•+ + 29和M•+ − 31，以及同时含有羟基和羧基的化合物的离子m/z M•+ + 1、M•+ + 29、M•+ − 31和M•+ − 17。然而，当使用第二步衍生化（BSTFA）时，同时含有羟基和羧基的化合物除了之前观察到的离子外，还显示出m/z M•+ + 73、M•+ − 15、M•+ − 59、M•+ − 75、M•+ − 89和73的离子。据我们所知，这项技术首次系统地描述了一种鉴定同时含有一个或多个羟基和羧酸基团的多官能团含氧化合物的方法。
• Antibiotic oxazolidinone derivatives
  申请人：Zeneca Ltd.

  公开号：US06365751B1

  公开（公告）日：2002-04-02

  The invention concerns a compound of the formula (I): wherein, for example: R1 is of the formula —NHC(═O)Rb wherein Rb is, for example, (1-4C)alkyl; R2 and R3 are hydrogen or fluoro; R2 and R3 are hydrogen or fluoro; D is O; R4 and R5 are hydrogen, (1-4C)alkyl or AR-oxymethyl; AR is phenyl or phenyl(1-4C)alkyl; R6 is hydrogen; >A—B— is of the formula >C═C(Ra)—, >CHCHRa—, or >C(OH)CHRa— (> represents two single bonds) wherein Ra is hydrogen or (1-4C)alkyl; and pharmaceutically-acceptable salts thereof; processes for their preparation; pharmaceutical compositions containing them and their use as antibacterial agents.

  本发明涉及如下公式(I)的化合物：其中，例如：R1是如下公式的形式—NHC(═O)Rb，其中Rb例如为(1-4C)烷基；R2和R3是氢或氟；D是氧；R4和R5是氢，(1-4C)烷基或AR-甲氧基甲基；AR是苯基或苯基(1-4C)烷基；R6是氢；>A—B—是如下公式的形式>C═C(Ra)—, >CHCHR_a—, 或 >C(OH)CHR_a—（>代表两个单键），其中Ra是氢或(1-4C)烷基；以及它们的药用可接受盐；它们的制备过程；含有它们的药物组合物以及它们作为抗菌剂的用途。
• [EN] BICYCLIC IMIDAZOL DERIVATIVES AGAINST FLAVIVIRIDAE<br/>[FR] DERIVES DE L'IMIDAZOLE BICYCLIQUES DIRIGES CONTRE LES FLAVIVIRIDAE
  申请人：GENELABS TECH INC

  公开号：WO2005012288A1

  公开（公告）日：2005-02-10

  Disclosed are compounds, compositions and methods for treating Flaviviridae family virus infections.

  揭示了用于治疗黄病毒科病毒感染的化合物、组合物和方法。
• Analysis of α-acyloxyhydroperoxy aldehydes with electrospray ionization-tandem mass spectrometry (ESI-MSⁿ)
  作者：Bartłomiej Witkowski、Tomasz Gierczak

  DOI：10.1002/jms.3130

  日期：2013.1

  α‐acyloxyhydroperoxy aldehydes. Ionization conditions were optimized. [M + H]+ ions were not formed in ESI; consequently, α‐acyloxyhydroperoxy aldehydes were identified as their ammonia adducts for the first time. On the other hand, atmospheric‐pressure chemical ionization has led to decomposition of the compounds of interest. Analysis of the mass spectra (MS2 and MS3) of the [M + NH4]+ ions allowed recognizing

  用直接注入电喷雾串联质谱（ESI / MS n）以及液相色谱和质谱（LC / MS）分析了一系列α-酰氧基氢过氧醛。α-酰氧基氢过氧醛的标准品是在羧酸存在下，通过环己烯的液相臭氧分解法制得的。稳定的Criegee中间体（SCI）是臭氧攻击环己烯双键的副产物，它与选定的羧酸（SCI清除剂）反应，导致形成α-酰氧基氢过氧醛。优化电离条件。[M + H] +ESI中没有形成离子；因此，首次将α-酰氧基氢过氧醛鉴定为其氨加成物。另一方面，大气压化学电离导致目标化合物的分解。[M + NH 4 ] +的质谱（MS 2和MS 3）分析离子可以识别所有研究化合物共有的碎片化途径。为了深入了解片段化机制，还研究了许多同位素标记的类似物。为了确认这种断裂机理可以预测不同的α-酰氧基氢过氧醛的质谱，对α-pine烯（一种非常重要的次要有机气溶胶前体）进行了臭氧分解。用α-ne烯，顺式制备的两种铵阳离子化的α-
• Nickel-Catalyzed Decarboxylative Coupling of Redox-Active Esters with Aliphatic Aldehydes
  作者：Jichao Xiao、Zhenning Li、John Montgomery

  DOI：10.1021/jacs.1c11170

  日期：2021.12.22

  The addition of alkyl fragments to aliphatic aldehydes is a highly desirable transformation for fragment couplings, yet existing methods come with operational challenges related to the basicity and instability of the nucleophilic reagents commonly employed. We report herein that nickel catalysis using a readily available bioxazoline (BiOx) ligand can catalyze the reductive coupling of redox-active

  将烷基片段添加到脂肪醛中是非常理想的片段偶联转化，但现有方法面临与常用亲核试剂的碱性和不稳定性相关的操作挑战。我们在本文中报道，使用易于获得的生物恶唑啉 (BiOx) 配体进行镍催化可以催化氧化还原活性酯与脂肪醛的还原偶联，使用锌金属作为还原剂以提供甲硅烷基保护的仲醇。该协议操作简单，在温和的条件下进行，并容忍各种功能组。最初的机制研究表明存在一种激进的链途径。此外，

表征谱图