4-(4-氯苯基)环己基羧酸 | 95233-37-7

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(4-氯苯基)环己基羧酸
• 中文别名: (1s,4s)-4-(4-氯苯基)环丙烷-1-甲酸；4-(4-氯苯基)环己烷羧酸；4-(4-氯苯基)环己基-1-羧酸；4-(4-氯苯基)环己烷甲酸
• 英文名称: 4-(4-chlorophenyl)cyclohexane-1-carboxylic acid
• 英文别名: 4-(4-chlorophenyl)cyclohexanecarboxylic acid；4-(4-chlorophenyl)cyclohexylcarboxylic acid；trans-4-(p-chlorophenyl)cyclohexane carboxylic acid
• CAS: 95233-37-7
• 化学式: C₁₃H₁₅ClO₂
• mdl: MFCD00665919
• 分子量: 238.714
• InChiKey: NXXDIEYTMQYWJU-UHFFFAOYSA-N

物化性质

• 熔点：
  250 °C
• 沸点：
  387.1±42.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S22,S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2916399090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  室温且干燥

SDS

Name:	4-(4-Chlorophenyl)cyclohexanecarboxylic acid 97% Material Safety Data Sheet
Synonym:
CAS:	95233-37-7

Section 1 - Chemical Product MSDS Name:4-(4-Chlorophenyl)cyclohexanecarboxylic acid 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
95233-37-7	4-(4-Chlorophenyl)cyclohexanecarboxyli	97%	unlisted

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# 95233-37-7: 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: 255 - 257 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: C13H15ClO2
Molecular Weight: 238.71

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents, reducing agents.
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# 95233-37-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-(4-Chlorophenyl)cyclohexanecarboxylic acid - 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# 95233-37-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 95233-37-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 95233-37-7 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

制备方法与用途

用途：阿托伐醌中间体

反应信息

• 作为反应物：
  描述：

  4-(4-氯苯基)环己基羧酸 在 氢氧化钾 、 ammonium peroxydisulfate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 atovaquone
  参考文献：
  名称：

  Synthesis of atovaquone

  摘要：

  A short synthesis of atovaquone 1 is achieved via the radical coupling of the trans-1,4-sbustituted cyclohexyl mono-oxalate 2 and 2-chloronapthoquinone under phase transfer conditions. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01691-8
• 作为产物：
  描述：

  4-羟基环己甲酸甲酯 在 吡啶 、 水 、 1,3-丁二烯 、 nickel dichloride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 4-(4-氯苯基)环己基羧酸
  参考文献：
  名称：

  一种药物中间体4-(4-氯苯基)环己基-1-甲酸 的合成方法

  摘要：

  本发明属于药物中间体制备领域，尤其涉及一种药物中间体4‑(4‑氯苯基)环己基‑1‑甲酸的合成方法，先将化合物I在缚酸剂的存在下与R2SO2Cl反应，得到化合物II；再将化合物II与格氏试剂4‑氯苯基卤化镁在催化剂作用下，经催化偶联反应得到化合物III；最后将化合物III在碱液中水解，得到目标产物4‑(4‑氯苯基)环己基‑1‑甲酸。本发明反应路线中各步骤均为专一反应，不存在傅克反应中的邻位、间位问题，因此原材料的利用率高，总收率高，成本低。且本发明使用偶联技术进行主体结构的构建，避免了傅克反应中使用的大量路易斯酸量水解后形成的水解液需要特殊处理等问题，绿色环保，利于工业化生产。

  公开号：

  CN104628555B

文献信息

• [EN] TRICYCLIC HETEROCYCLIC COMPOUNDS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES TRICYCLIQUES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2011059784A1

  公开（公告）日：2011-05-19

  Disclosed are compounds of Formula (I) or stereoisomers or salts thereof, wherein: X1, X2, X3, W, Q1, Q2, and G2 are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

  揭示了Formula (I)的化合物或其立体异构体或盐，其中：X1、X2、X3、W、Q1、Q2和G2在此处被定义。还揭示了将这些化合物用作G蛋白偶联受体S1P1的选择性激动剂的方法，以及包含这些化合物的药物组合物。这些化合物在治疗、预防或减缓多种治疗领域的疾病或疾病的进展方面是有用的，如自身免疫疾病和血管疾病。
• Photoredox/Cobalt Dual‐Catalyzed Decarboxylative Elimination of Carboxylic Acids: Development and Mechanistic Insight
  作者：Kaitie C. Cartwright、Ebbin Joseph、Chelsea G. Comadoll、Jon A. Tunge

  DOI：10.1002/chem.202001952

  日期：2020.9.25

  Recently, dual‐catalytic strategies towards the decarboxylative elimination of carboxylic acids have gained attention. Our lab previously reported a photoredox/cobaloxime dual catalytic method that allows the synthesis of enamides and enecarbamates directly from N‐acyl amino acids and avoids the use of any stoichiometric reagents. Further development, detailed herein, has improved upon this transformation's

  近来，用于羧酸脱羧消除的双重催化策略已引起关注。我们的实验室以前曾报道过光氧化还原/钴肟双催化方法，该方法可直接从N酰基氨基酸合成酰胺和烯甲酸酯，并避免使用任何化学计量试剂。本文详述的进一步开发改进了这种转化的用途，进一步的实验为反应机理提供了新的见解。这些新的发展和见识有望帮助扩大光氧化还原/钴双催化系统。
• [EN] FARNESOID X RECEPTOR AGONISTS AND USES THEREOF<br/>[FR] AGONISTES DU RÉCEPTEUR X FARNÉSOÏDE ET LEURS UTILISATIONS
  申请人：METACRINE INC

  公开号：WO2017049177A1

  公开（公告）日：2017-03-23

  Described herein are compounds that are farnesoid X receptor agonists, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders associated with farnesoid X receptor activity.

  本发明涉及法尼醇X受体激动剂化合物，制造此类化合物的方法，包含此类化合物的药物组合物和药品，以及使用此类化合物治疗与法尼醇X受体活性相关的状况、疾病或失调的方法。
• Ligand-controlled divergent dehydrogenative reactions of carboxylic acids via C–H activation
  作者：Zhen Wang、Liang Hu、Nikita Chekshin、Zhe Zhuang、Shaoqun Qian、Jennifer X. Qiao、Jin-Quan Yu

  DOI：10.1126/science.abl3939

  日期：2021.12.3

  inaccessible with existing carbonyl desaturation protocols. Product inhibition is overcome through ligand-promoted preferential activation of C(sp3)–H bonds over C(sp2)–H bonds or a tandem dehydrogenation or vinyl C–H alkynylation sequence. The dehydrogenation reaction is compatible with molecular oxygen as the terminal oxidant.

  通过亚甲基 C-H 活化将烷基链脱氢转化为烯烃仍然是一个重大挑战。我们报道了两类吡啶-吡啶酮配体，它们通过钯催化的β-亚甲基C-H活化羧酸实现不同的脱氢反应，从而直接合成α,β-不饱和羧酸或γ-亚烷基丁烯内酯。这对反应的定向性质允许在其他烯醇化官能团（例如酮）存在下对羧酸进行化学选择性脱氢，从而提供现有羰基去饱和方案无法实现的化学选择性。通过配体促进的 C(sp 3 )–H 键相对于 C(sp 2 )–H 键的优先激活或串联脱氢或乙烯基 C–H 炔基化序列来克服产物抑制。脱氢反应与分子氧作为末端氧化剂相容。
• Synthesis and Biological Evaluation of 4-(4-Chlorophenyl)cyclohexane Carbohydrazide Derivatives as Anti-Bacterial Agents
  作者：G. Venkatasatyanarayana、V. Lakshmana Rao、M. Thirumala Chary、B. Ram、B. Balram、E. Laxminarayana

  DOI：10.14233/ajchem.2015.18731

  日期：——

  The present paper describes the synthesis and antibacterial activity of novel hydrazone derivatives 4a-s derived from 4-(4-chlorophenyl)-cyclohexane carboxylic acid. All the ninteen newly synthesized novel hydrazone derivatives 4a-s were evaluated for their in vitro antibacterial activity against Staphylococcus aureus and S. pyogenes (Gram-positive bacteria) and Escherichia coli and Pseudomonas aeruginosa (Gram-negative bacteria). Antibacterial activity data revealed that the basic scaffold with R = nitrogen heterocyclic ring such as pyridine, quinoline, imidazole and indole showed significant antibacterial activity (excellent activity), whereas the hetrocyclic ring like benzo[b]furan, furan, thiophene moiety showed good antibacterial activity.

  本文介绍了由4-(4-氯苯基)-环己烷羧酸衍生得到的新型腙衍生物4a-s的合成及其抗菌活性。对所合成的十九种新型腙衍生物4a-s进行了体外抗菌活性测试，针对金黄色葡萄球菌和大肠杆菌（革兰氏阳性菌）以及铜绿假单胞菌和痢疾杆菌（革兰氏阴性菌）。抗菌活性数据显示，当R为含氮杂环如吡啶、喹啉、咪唑和吲哚时，基本骨架显示出显著的抗菌活性（优秀活性），而如苯并[b]呋喃、呋喃、噻吩等杂环则显示出良好的抗菌活性。