3-氯金刚烷-1-羧酸 | 34859-74-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 3-氯金刚烷-1-羧酸
• 中文别名: 3-氯金刚烷羧酸
• 英文名称: 3-chloroadamantane-1-carboxylic acid
• CAS: 34859-74-0
• 化学式: C₁₁H₁₅ClO₂
• mdl: MFCD00167831
• 分子量: 214.692
• InChiKey: GMOBHRQSNDDZAD-UHFFFAOYSA-N

物化性质

• 熔点：
  136 °C
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，没有已知危险反应。请避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.909
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2916209090
• 储存条件：
  保持贮藏器密封，储存在阴凉、干燥的地方，并确保工作间有良好的通风或排气装置。

SDS

Name:	3-Chloroadamantane-1-carboxylic acid 97% Material Safety Data Sheet
Synonym:
CAS:	34859-74-0

Section 1 - Chemical Product MSDS Name:3-Chloroadamantane-1-carboxylic acid 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
34859-74-0	3-Chloroadamantane-1-carboxylic acid	97%	unlisted

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. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes 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. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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:
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# 34859-74-0: 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: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 136 - 140 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: C11H15ClO2
Molecular Weight: 215

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents, bases.
Hazardous Decomposition Products:
Hydrogen chloride, chlorine, carbon monoxide, carbon dioxide, acrid smoke and fumes.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 34859-74-0: AU4452700 LD50/LC50:
Not available.
Carcinogenicity:
3-Chloroadamantane-1-carboxylic acid - 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
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: 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# 34859-74-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 34859-74-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 34859-74-0 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：

  3-氯金刚烷-1-羧酸 在 (trimethylstannyl)lithium 、 2-碘-1,1,1-三氟乙烷 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 3.25h， 生成 金刚烷
  参考文献：
  名称：

  Mechanistic definition of trimethylstannylation of 1,3-dihaloadamantanes: delocalized radical anions as possible intermediates

  摘要：

  A series of 1,3-dihaloadamantanes (3, X = Y = halogens) have been synthesized, characterized, and treated with (trimethylstannyl) alkali reagents (Me3SnM, M = Li or Na) in the absence and presence of tert-butylamine (TBA) and dicyclohexylphosphine (DCPH). The product distributions of these reactions have been established by C-13 and Sn-119 NMR spectroscopy and vapor-phase chromatographic analyses. Tin substitution via an S(RN)1-type pathway is shown to be a significant reaction for several of the derivatives of 3 (X = F, Y Br or I; X = Cl, Y = Br or I; X = Y = Br) but not for the bromo iodide or diiodide (3, X = Br, Y = I and X = Y = I). For the latter two compounds, the formation of 1,3-dehydroadamantane or propellane 8 is the predominant reaction product while tin substitution is insignificant. Propellane 8 formation is also a significant reaction product for some of the other dihalo derivatives of 3 (X = Cl, Y = I and X = Y = Br) but not for others (3, X = F, Y = Br or I and X = Cl, Y = Br). The mechanism of formation of 8 is perplexing in light of the trapping experiments in the presence of TBA and DCPH. A possible pathway is proposed in which the key intermediate is a delocalized radical anion.

  DOI：

  10.1021/jo00078a009
• 作为产物：
  描述：

  1-金刚烷甲酸 在 一氯化碘 作用下， 以 四氯化碳 为溶剂， 反应 5.0h， 以83%的产率得到3-氯金刚烷-1-羧酸
  参考文献：
  名称：

  金刚烷衍生物的液相卤化机理

  摘要：

  介绍了金刚烷衍生物卤化过程的新型机理表示。

  DOI：

  10.1016/s0040-4039(00)84269-0

文献信息

• Photoredox Synthesis of Arylhydroxylamines from Carboxylic Acids and Nitrosoarenes
  作者：Nadeem Sheikh、Daniele Leonori、Jacob Davies、Lucrezia Angelini、Mohammed Alkhalifah、Laia Sanz

  DOI：10.1055/s-0036-1591744

  日期：2018.2

  direct conversion of carboxylic acids into the corresponding alkylhydroxylamines using organo-photoredox catalysis is reported. The process relies in the generation of alkyl radicals via photoinduced oxidation-decarboxylation and their following reaction with nitrosoarenes. We have successfully applied this method to the late-stage modification of complex and biologically active acids and applied it in

  作为Bürgenstock专栏2017年有机化学中的未来之星的一部分发布 抽象的 羟胺存在于生物活性化合物中，并用作制备含氮分子的基础。此处报道了使用有机光氧化还原催化将羧酸直接转化为相应的烷基羟胺的方法。该方法依赖于通过光诱导的氧化-脱羧作用及其随后与亚硝基芳烃的反应来产生烷基。我们已成功地将此方法应用于复杂的生物活性酸的后期修饰，并将其应用于新型自由基级联过程。 羟胺存在于生物活性化合物中，并用作制备含氮分子的基础。此处报道了使用有机光氧化还原催化将羧酸直接转化为相应的烷基羟胺的方法。该方法依赖于通过光诱导的氧化-脱羧作用及其随后与亚硝基芳烃的反应来产生烷基。我们已成功地将此方法应用于复杂的生物活性酸的后期修饰，并将其应用于新型自由基级联过程。
• Direct Hydrodecarboxylation of Aliphatic Carboxylic Acids: Metal- and Light-Free
  作者：Euan B. McLean、David T. Mooney、David J. Burns、Ai-Lan Lee

  DOI：10.1021/acs.orglett.1c04079

  日期：2022.1.21

  A mild and inexpensive method for direct hydrodecarboxylation of aliphatic carboxylic acids has been developed. The reaction does not require metals, light, or catalysts, rendering the protocol operationally simple, easy to scale, and more sustainable. Crucially, no additional H atom source is required in most cases, while a broad substrate scope and functional group tolerance are observed.

  已经开发了一种用于脂肪族羧酸直接加氢脱羧的温和且廉价的方法。该反应不需要金属、光或催化剂，使该协议操作简单、易于扩展且更具可持续性。至关重要的是，在大多数情况下不需要额外的 H 原子源，同时观察到广泛的底物范围和官能团耐受性。
• TRIAZOLE-ISOXAZOLE COMPOUND AND MEDICAL USE THEREOF
  申请人：JAPAN TOBACCO INC.

  公开号：US20160137639A1

  公开（公告）日：2016-05-19

  A compound represented by Formula [I]: or pharmaceutically acceptable salt thereof, wherein each symbol is as defined in the description.

  由式[I]表示的化合物： 或其药学上可接受的盐，其中每个符号如描述中所定义。
• Synthesis and Identification of Novel Berberine Derivatives as Potent Inhibitors against TNF-α-Induced NF-κB Activation
  作者：Yan-Xiang Wang、Lu Liu、Qing-Xuan Zeng、Tian-Yun Fan、Jian-Dong Jiang、Hong-Bin Deng、Dan-Qing Song

  DOI：10.3390/molecules22081257

  日期：——

  A preliminary mechanism study revealed that all of them could inhibit TNF-α-induced NF-κB activation via impairing IκB kinase (IKK) phosphorylation as well as cytokines interleukin (IL)-6 and IL-8 induced by TNF-α. Therefore, the results provided powerful information on further structural modifications and development of BBR derivatives into a new class of anti-inflammatory candidates for the treatment

  合成了在环D的取代基上定义的二十三种新的小碱（BBR）类似物，并评估了其抑制肿瘤坏死因子（TNF）-α诱导的核因子（NF）-κB活化的活性。结构-活性关系（SAR）分析表明，在9位上合适的叔/季碳取代基或10位上的刚性片段可能有利于增强其抗炎能力。其中，化合物2d，2e，2i和2j对NF-κB活化表现出令人满意的抑制作用，抑制率约为90％（5μM），远优于BBR。初步的机制研究表明，它们均可以通过削弱IκB激酶（IKK）磷酸化以及TNF-α诱导的细胞因子白介素（IL）-6和IL-8来抑制TNF-α诱导的NF-κB活化。所以，
• PhSO₂SCF₂H: A Shelf-Stable, Easily Scalable Reagent for Radical Difluoromethylthiolation
  作者：Dianhu Zhu、Xinxin Shao、Xin Hong、Long Lu、Qilong Shen

  DOI：10.1002/anie.201609468

  日期：2016.12.19

  A new shelf‐stable and easily scalable difluoromethylthiolating reagent S‐(difluoromethyl) benzenesulfonothioate (PhSO2SCF2H) was developed. PhSO2SCF2H is a powerful reagent for radical difluoromethylthiolation of aryl and alkyl boronic acids, decarboxylative difluoromethylthiolation of aliphatic acids, and a phenylsulfonyl‐difluoromethylthio difunctionalization of alkenes under mild reaction conditions

  开发了一种新的货架稳定且易于扩展的二氟甲基硫醇化试剂S-（二氟甲基）苯磺酸硫（PhSO 2 SCF 2 H）。PhSO 2 SCF 2 H是用于在温和的反应条件下进行芳基和烷基硼酸的自由基二氟甲硫基化，脂肪酸的脱羧二氟甲硫基化以及烯烃的苯磺酰基-二氟甲硫基二官能化的强大试剂。