2-乙酰基-4-氰基苯酚 | 35794-84-4

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物 - 酚及其卤化、磺化、硝化或亚硝化衍生物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-乙酰基-4-氰基苯酚
• 中文别名: 2-乙酰基对氰基苯酚；3-乙酰基-4-羟基苯腈
• 英文名称: 2-hydroxy-5-cyanoacetophenone
• 英文别名: 3-Acetyl-4-hydroxy-benzonitrile；2-Acetyl-4-cyanophenol；3-acetyl-4-hydroxybenzonitrile
• CAS: 35794-84-4
• 化学式: C₉H₇NO₂
• mdl: MFCD00100432
• 分子量: 161.16
• InChiKey: HSZUUVJFZOGAMB-UHFFFAOYSA-N

物化性质

• 熔点：
  103 °C
• 沸点：
  313.5±32.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温且干燥环境下使用。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 2-Acetyl-4-cyanophenol
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 2-Acetyl-4-cyanophenol
CAS number: 35794-84-4

---

Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

---

Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

---

Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

---

Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

---

Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

---

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C9H7NO2
Molecular weight: 161.2

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-乙酰基-4-氰基苯酚 在 sodium azide 、 ammonium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以56%的产率得到1-[2-hydroxy-5-(1H-tetrazol-5-yl)-phenyl]-ethanone
  参考文献：
  名称：

  羧基查耳酮的合成与构效关系：CysLT1（LTD4）受体拮抗剂的新系列。

  摘要：

  一系列新的2-，3-和4-（2-喹啉基甲氧基）-和3-和4- [2-（2-喹啉基）乙烯基]-取代的2'-，3的合成及CysLT1拮抗活性描述了'-，4'-或5'-羧基查耳酮。结构-活性关系研究表明，优选带负电的（酸性）部分，尽管在某些情况下腈或酯类似物也具有中等活性。喹啉部分可以在3-或4-位被取代。用其他芳香族基团取代该杂环会导致化合物具有可比的亲和力[2-（7-氯喹啉），1-（1-甲基-2-苯并咪唑）或1-（2-苯并噻唑）]或具有较低的活性[1 -（1-乙氧基乙基）-2-苯并咪唑，2-萘基或苯基]。喹啉和查耳酮部分可以通过乙烯基或甲氧基间隔基连接。对于3-和4-取代的查耳酮，查耳酮B环上的酸性部分可以连接至2'-，3'-，4'-或5'-位置。没有一般模式可以指定哪个取代位置产生最有效的化合物。该系列包含几种有效的CysLT1受体拮抗剂，其K（D）值接近纳摩尔范围，通过[3H] LTD4

  DOI：

  10.1021/jm960628d
• 作为产物：
  描述：

  4-羟基苯甲腈 在 aluminum (III) chloride 、 sodium hydroxide 作用下， 生成 2-乙酰基-4-氰基苯酚
  参考文献：
  名称：

  苯并吡喃衍生物作为KATP通道开放剂的设计，合成及生物学评价

  摘要：

  为了完成SAR并发现新的有效PCO和选择性PCO，对克罗马卡林的C-4和C-2替代品进行了一些更改。合成并评价了一系列与cromakalim结构相关的4-氨基酸取代的-2,2-二烷基苯并二氢吡喃，作为ATP敏感的钾通道开放剂（8a-1）。初步生物学测试表明，这些化合物对KCl收缩的大鼠主动脉条显示出对轻度松弛活性的作用。化合物8b（IC50 =0.25μM），8f（IC50 =6.44μM）和8j（IC50 =8.65μM）表现出值得称赞的钾通道开放活性。除了抗高血压外，这些化合物还可被视为进一步开发心肌抗缺血药物的主要候选药物。

  DOI：

  10.2174/157018010791306560
• 作为试剂：
  描述：

  2-乙酰基-4-氰基苯酚 、 1,3-二甲氧基乙酮 在 2-乙酰基-4-氰基苯酚 作用下， 以61的产率得到6-cyano-3,4-dihydro-2,2-bis(methoxymethyl)-2H-1-benzopyran-4-one
  参考文献：
  名称：

  J. Med. Chem. 1996, 39, 3797-3805

  摘要：

  DOI：

文献信息

• Chroman derivative and pharmaceutical use thereof
  申请人：Japan Tobacco Inc.

  公开号：US05719155A1

  公开（公告）日：1998-02-17

  Chroman derivatives of the formula \x9bI! ##STR1## wherein R.sup.1 is a cyano, a nitro, a trihalomethyl, a trihalomethoxy or a halogen atom; R.sup.2 is a lower alkoxyalkyl, an aryloxyalkyl or a dialkoxyalkyl; R.sup.3 is a lower alkoxyalkyl or an aryloxyalkyl; R.sup.4 is a hydroxy, a formyloxy or a lower alkanoyloxy; X is N--H, an N--optionally substituted lower alkyl, an oxygen atom, a sulfur atom or a single bond; and Y is an optionally substituted aromatic ring residue or an optionally substituted heterocyclic residue, pharmaceutically acceptable salts thereof and pharmaceutical use thereof. The compound of the present invention and pharmaceutically acceptable salts thereof have selective and excellent coronary vasodilating action and extremely weak hypotensive action. Accordingly, it is possible to selectively increase the coronary blood flow without causing a sudden hypotention causative of tachycardia which has a detrimental effect on the heart, and they are useful as a coronary vasodilator, in particular, an agent for the prophylaxis and treatment of cardiovascular disorders such as angina pectoris and heart failure.

  本发明的化合物及其中医药学上可接受的盐具有选择性和优秀的心脏血管扩张作用，而且具有极其微弱的降压作用。因此，可以在不引起心动过速导致的有害心脏影响的突发性低血压的情况下，选择性地增加冠状动脉血流，并且它们作为心脏血管扩张剂特别有用，尤其是用于预防和治疗心绞痛和心力衰竭等心血管疾病的药物。
• HETEROCYCLIC COMPOUND
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2123652A1

  公开（公告）日：2009-11-25

  The present invention provides a compound having an ACC inhibitory action, which is useful for the prophylaxis or treatment of obesity, diabetes, hypertension, hyperlipidemia, cardiac failure, diabetic complications, metabolic syndrome, sarcopenia, cancer and the like, and has superior efficacy. The present invention provides a compound represented by the formula (I): wherein each symbol is as in the specification, or a salt thereof.

  本发明提供了一种具有ACC抑制作用的化合物，该化合物用于预防或治疗肥胖、糖尿病、高血压、高脂血症、心力衰竭、糖尿病并发症、代谢综合征、肌肉减少症、癌症等疾病，并具有优异的疗效。 本发明提供了一种由公式（I）表示的化合物： 其中每个符号如说明书所述，或其盐。
• Potent Inhibitors of Phosphatidylinositol 3 (PI3) Kinase that have Antiproliferative Activity Only When Delivered as Prodrug Forms
  作者：Nathan J. O'Brien、Syazwani Amran、Jelena Medan、Ben Cleary、Leslie W. Deady、Ian G. Jennings、Philip E. Thompson、Belinda M. Abbott

  DOI：10.1002/cmdc.201200583

  日期：2013.6

  Prodrugs for PI3K: A series of substituted analogues of the phosphatidylinositol 3 kinase (PI3K) inhibitor LY294002 were prepared and found to potently inhibit the isolated enzyme but not MCF7 cell proliferation. Two tetrazolyl‐substituted analogues were further derivatized as prodrugs resulting in restoration of cell‐based activity. These data provide a conceptual model for development of tumor‐targeting

  PI3K的前药：制备了磷脂酰肌醇3激酶（PI3K）抑制剂LY294002的一系列取代类似物，发现它们能有效抑制分离的酶，但不能抑制MCF7细胞的增殖。两个四唑基取代的类似物被进一步衍生为前药，从而恢复了基于细胞的活性。这些数据为细胞不可渗透的PI3K抑制剂的靶向肿瘤前药形式的开发提供了概念模型。
• An Efficient Microwave-Assisted Propylphosphonic Anhydride (T3P®)-Mediated One-Pot Chromone Synthesis via Enaminones
  作者：Manoranjan Behera、C. Balakrishna、Venu Kandula、Ramakrishna Gudipati、Satyanarayana Yennam、P. Devi

  DOI：10.1055/s-0036-1591898

  日期：2018.5

  An efficient synthesis of 4H-chromene-4-ones via enamino ketones, with cyclization by using T3P® under microwave heating is described. This is the first report for the synthesis of chromones by using T3P®. Significant features of this method include short reaction times and high-purity products.

  描述了通过烯氨基酮有效合成 4H-色烯-4-酮，并在微波加热下使用 T3P® 环化。这是使用 T3P® 合成色酮的第一份报告。该方法的显着特点包括反应时间短和产品纯度高。
• Synthesis of <scp> 2 <i>H</i> </scp> ‐benzo[ <i>g</i> ]furo/thieno/pyrrolo[2,3‐ <i>e</i> ]indazoles <i>via</i> Intramolecular Dehydrogenation Photocyclization
  作者：Wei Zhang、Ping Wang、Xi Zhang、Rui Wang、Tao Wang、Zhicun Liu、Zunting Zhang

  DOI：10.1002/cjoc.202100103

  日期：2021.8

  A catalyst-, acid- and base-free, environmental-friendly method for synthesis of 2H-benzo[g]furo[2,3-e]indazoles, 2H-benzo[g]thieno[2,3-e]indazoles and 2H-benzo[g]pyrrolo[2,3-e]indazoles via UV light irradiation of 3-phenyl-4-(2-heteroaryl)pyrazoles (aryl = furanyl, thiophenyl and N-methylpyrrolyl) in EtOH/H2O at room temperature under argon atmosphere was described. Irradiation of 3-(2-hydroxyphe

  经催化剂，酸和碱免费，对于2合成环境友好的方法ħ -苯并[克]呋喃并[2,3- ë ]吲唑，2 ħ苯并[克]噻吩并[2,3- ë ]吲唑和 2 H-苯并[ g ]吡咯并[2,3- e ]吲唑通过紫外光照射 3-苯基-4-（2-杂芳基）吡唑（芳基 = 呋喃基、噻吩和N-甲基吡咯基）在 EtOH/H 中描述了室温下氩气气氛下的2 O。的3-（2-羟基苯基）照射-4-（2-杂芳基）吡唑显示出高的化学-选择性以获得脱氢产物2 ħ苯并[g ]呋喃/噻吩/吡咯并[2,3 - e ]吲唑-10-醇。通过6π-电子环化、[1,5]-氢位移、吡唑互变异构、1,3-烯胺互变异构和H 2演化过程阐述了光环化的机理。