1-苯基-1-氰基环戊烷 | 77-57-6

• 物质功能分类: 化学试剂 - 有机试剂 - 氰化物/腈
• 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: 1-苯基-1-氰基环戊烷
• 中文别名: 1-苯基环戊烷甲腈；1-苯基环戊腈；1-苯基-1-环戊烷甲腈
• 英文名称: 1-phenyl-1-cyclopentanecarbonitrile
• 英文别名: 1-phenylcyclopentane-1-carbonitrile；1-Phenylcyclopentanecarbonitrile
• CAS: 77-57-6
• 化学式: C₁₂H₁₃N
• 分子量: 171.242
• InChiKey: GDXMFFGTPGAGGX-UHFFFAOYSA-N

物化性质

• 沸点：
  135-140 °C (10 mmHg)
• 密度：
  1.03
• 稳定性/保质期：

  与强氧化剂反应。

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R20/21/22,R36/37/38
• 海关编码：
  29269095
• WGK Germany：
  3
• 危险类别：
  6.1
• 包装等级：
  III
• 危险品运输编号：
  3276
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H312,H315,H319,H332,H335
• 储存条件：
  密封贮藏，存放在阴凉干燥的地方。

SDS

Name:	1-PHENYL-1-CYCLOPENTANECARBONITRILE Material Safety Data Sheet
Synonym:
CAS:	77-57-6

Section 1 - Chemical Product MSDS Name:1-PHENYL-1-CYCLOPENTANECARBONITRILE Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
77-57-6	1-PHENYL-1-CYCLOPENTANECARBONITRILE		201-038-2

Hazard Symbols: XN
Risk Phrases: 20/21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Potential Health Effects
The toxicological properties of this material have not been investigated. Use appropriate procedures to prevent opportunities for direct contact with the skin or eyes and to prevent inhalation.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids.
Skin:
Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
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.
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:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

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Section 7 - HANDLING and STORAGE
Handling:
Not available.
Storage:
Not available.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate general or local exhaust ventilation to keep airborne concentrations below the permissible exposure limits.
Exposure Limits CAS# 77-57-6: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves and clothing to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
Wear a NIOSH/MSHA or European Standard EN 149 approved full-facepiece airline respirator in the positive pressure mode with emergency escape provisions.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Not available.
Color: Not available.
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 135.0 - 142.0 deg C @ 10.00mmHg
Freezing/Melting Point: 0 deg C
Autoignition Temperature: Not available.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H13N
Molecular Weight: 171.24

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Not available.
Incompatibilities with Other Materials:
Strong oxidizing agents - strong bases.
Hazardous Decomposition Products:
Not available.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 77-57-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-PHENYL-1-CYCLOPENTANECARBONITRILE - 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
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
IMO
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
RID/ADR
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 77-57-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 77-57-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 77-57-6 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

化学性质：沸点为135-142℃（1.33kPa）。

用途：用作止咳药“咳美芬”和“咳必清”的中间体。

生产方法：通过1,4-二溴丁烷与氰苄的环合反应制得。具体步骤如下：将氰苄加入干燥的反应锅中，搅拌下慢慢加入氢氧化钠并加热至50-55℃，保温2小时后，缓缓滴加1,4-二溴丁烷。继续自然升温至85-90℃，保温4小时后，加水进行分层，并减压蒸馏得到产物1-苯基-1-氰基环戊烷。

反应信息

• 作为反应物：
  描述：

  1-苯基-1-氰基环戊烷 在 sodium hydride 、 sodium iodide 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 17.0h， 以61 mg的产率得到环戊基苯
  参考文献：
  名称：

  氢化物-碘化物复合材料的氢化物还原

  摘要：

  氢化钠（NaH）在化学合成中被广泛用作布朗斯台德碱，并与各种布朗斯台德酸发生反应，而它几乎不通过将氢化物传递给极性π亲电试剂来充当还原剂。这项研究提出了在LiI或NaI存在下，NaH使腈，酰胺和亚胺发生的一系列还原反应。这种非常简单的方案使NaH具有前所未有的独特的氢化物-给体化学反应性。

  DOI：

  10.1002/anie.201600305
• 作为产物：
  描述：

  苯乙腈 在 氨 、 sodium amide 作用下， 生成 1-苯基-1-氰基环戊烷
  参考文献：
  名称：

  Aminoesters of Substituted Alicylic Carboxylic Acids¹

  摘要：

  DOI：

  10.1021/ja01203a077

文献信息

• Inhibitors of acyl-CoA:cholesterol acyltransferase. 4. A novel series of urea ACAT inhibitors as potential hypocholesterolemic agents
  作者：Bharat K. Trivedi、Ann Holmes、Terri L. Stoeber、C. John Blankley、W. Howard Roark、Joseph A. Picard、Mary K. Shaw、Arnold D. Essenburg、Richard L. Stanfield、Brian R. Krause

  DOI：10.1021/jm00074a011

  日期：1993.10

  We have synthesized a series of N-phenyl-N'-aralkyl and N-phenyl-N'-(1-phenylcycloalkyl)ureas as inhibitors of acyl-CoA:cholesterol acyltransferase (ACAT). This intracellular enzyme is thought to be responsible for the esterification of dietary cholesterol; hence inhibition of this enzyme could reduce diet-induced hypercholesterolemia. For this series of compounds, the in vitro ACAT inhibitory activity

  我们合成了一系列的N-苯基-N'-芳烷基和N-苯基-N'-（1-苯基环烷基）脲作为酰基辅酶A：胆固醇酰基转移酶（ACAT）的抑制剂。人们认为这种细胞内酶负责饮食中胆固醇的酯化。因此抑制这种酶可以减少饮食引起的高胆固醇血症。对于这一系列化合物，通过增加苯环上2,6-取代基的体积来提高体外ACAT抑制活性。此外，我们发现芳环的间距对于ACAT抑制活性至关重要。离必需的2,6-二异丙基苯基部分5个原子的苯环对于体外活性而言是最佳的。N'-苯基部分被α取代增强了体外效能。就苯基环烷基脲而言，ACAT抑制活性与环烷基环的大小无关。从该系列类似物中，发现在高胆固醇血症动物模型中以50 mg / kg的饮食施用时，具有出色的体外抑制ACAT效力的化合物25在体内可使血浆胆固醇降低73％。在此模型中，化合物25依赖于降低血浆胆固醇剂量，并且与Lederle ACAT抑制剂CL 277082一样有效。
• Synthesis of α-Aryl Nitriles through Palladium-Catalyzed Decarboxylative Coupling of Cyanoacetate Salts with Aryl Halides and Triflates
  作者：Rui Shang、Dong-Sheng Ji、Ling Chu、Yao Fu、Lei Liu

  DOI：10.1002/anie.201006763

  日期：2011.5.2

  Worth its salt: The palladium‐catalyzed decarboxylative coupling of the cyanoacetate salt as well as its mono‐ and disubstituted derivatives with aryl chlorides, bromides, and triflates is described (see scheme). This reaction is potentially useful for the preparation of a diverse array of α‐aryl nitriles and has good functional group tolerance. S‐Phos=2‐(2,6‐dimethoxybiphenyl)dicyclohexylphosphine)

  值得其盐：描述了氰基乙酸盐及其与芳基氯化物，溴化物和三氟甲磺酸酯的钯催化的脱羧偶联反应（参见方案）。该反应对于制备各种α-芳基腈具有潜在的实用性，并具有良好的官能团耐受性。S-Phos = 2-（（2,6-二甲氧基联苯）二环己基膦），Xant-Phos = 4,5-双（二苯基膦基）-9,9-二甲基x吨。
• Palladium-Catalyzed Distal <i>m</i>-C–H Functionalization of Arylacetic Acid Derivatives
  作者：Dasari Srinivas、Gedu Satyanarayana

  DOI：10.1021/acs.orglett.1c02460

  日期：2021.10.1

  Herein, we present m-C–H olefination on derivatives of phenylacetic acids by tethering with a simple nitrile-based template through palladium catalysis. Notably, the versatility of the method is evaluated with a wide range of phenylacetic acid derivatives for obtaining the meta-olefination products in fair to excellent yields with outstanding selectivities under mild conditions. Significantly, the

  在此，我们通过钯催化与简单的腈基模板连接，在苯乙酸衍生物上进行m -C-H 烯化。值得注意的是，该方法的多功能性是用范围广泛的苯乙酸衍生物来评估的，以便在温和的条件下以中等至极好的收率和出色的选择性获得间烯烃化产物。重要的是，本策略成功地用于合成药物/天然产物类似物（萘普生、布洛芬、扑热息痛和胆固醇）。
• Dihydroxypyrimidine carbonic acid derivatives and their use in the treatment, amelioration or prevention of a viral disease
  申请人：SAVIRA PHARMACEUTICALS GMBH

  公开号：US20140038990A1

  公开（公告）日：2014-02-06

  The present invention relates to a compound having the general formula (Di), (Dii), or (Diii), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, codrug, cocrystal, prodrug, tautomer, racemate, enantiomer, or diastereomer or mixture thereof, which are useful in treating, ameloriating or preventing a viral disease. Furthermore, specific combination therapies are disclosed.

  本发明涉及具有一般式（Di）、（Dii）或（Diii）的化合物，可选地为药学上可接受的盐、溶剂合物、多型体、共药、共晶、前药、互变异构体、消旋体、对映体或二对映体或其混合物，这些化合物在治疗、改善或预防病毒性疾病方面是有用的。此外，还披露了特定的联合疗法。
• Hydration of Cyanohydrins by Highly Active Cationic Pt Catalysts: Mechanism and Scope
  作者：Chengcheng Li、Xiao-Yong Chang、Luqiong Huo、Haibo Tan、Xiangyou Xing、Chen Xu

  DOI：10.1021/acscatal.1c02254

  日期：2021.7.16

  Cyanohydrins (α-hydroxy nitriles) are a special type of nitriles that readily decompose into hydrogen cyanide (HCN) and the corresponding carbonyl compounds. Hydration of cyanohydrins that are readily available through cyanation of aldehydes and ketones provides the most straightforward route to valuable α-hydroxyamides. However, due to low stability of cyanohydrins and deactivation of the catalysts

  氰醇（α-羟基腈）是一种特殊类型的腈，很容易分解成氰化氢 (HCN) 和相应的羰基化合物。可通过醛和酮的氰化轻松获得的氰醇的水合提供了获得有价值的 α-羟基酰胺的最直接途径。然而，由于氰醇的低稳定性和释放的 HCN 使催化剂失活，氰醇的催化直接水合仍然在很大程度上未解决。一般来说，含有较大取代基的氰醇，如α,α-二芳基氰醇，降解速度更快，因此更难水合。在这里，我们报告了对各种氰醇的水合表现出高反应性的阳离子铂催化剂的开发。2 OH)X(OTf) 揭示了一个催化循环，包括形成五元金属环中间体，然后通过 H 2 O攻击二级氧化膦 (PR 2 OH) 配体的磷进行水解。我们发现 Pt 催化剂甲轴承富电子，适当小的咬角双膦配体提供了一种用于氰醇的水合反应性超级。由A催化的水合反应在环境温度下进行，并与多种氰醇一起发生，包括最难的 α,α-二芳基氰醇，具有良好的转化率。

表征谱图