3-methyl-2-thiophenecarboxaldoxime | 41056-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-methyl-2-thiophenecarboxaldoxime
• 英文别名: N-hydroxy(3-methylthiophen-2-yl)methanimine；3-methylthiophene-2-oxime；3-methylthiophene-2-carbaldehyde oxime；3-Methylthiophene-2-carboxaldehyde oxime；N-[(3-methylthiophen-2-yl)methylidene]hydroxylamine
• CAS: 41056-90-0
• 化学式: C₆H₇NOS
• mdl: MFCD00832733
• 分子量: 141.194
• InChiKey: ZZGCONMEXMLKLV-UHFFFAOYSA-N

物化性质

• 沸点：
  235.4±28.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 3-Methylthiophene-2-carbaldehyde oxime
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 3-Methylthiophene-2-carbaldehyde oxime
CAS number: 41056-90-0

---

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: C6H7NOS
Molecular weight: 141.2

---

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, sulfur 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：

  3-methyl-2-thiophenecarboxaldoxime 在 草酰氯 、 2,3-bis(4-methoxyphenyl)cyclopropenone 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以85%的产率得到3-甲基噻吩-2-腈
  参考文献：
  名称：

  环丙烯酮催化醛肟和伯酰胺直接转化为腈

  摘要：

  报道了使用环丙烯酮作为有机催化剂将醛肟和伯酰胺有效转化为腈类。反应在温和条件下顺利进行，催化剂负载量为 5 mol%，在一次操作中以优异的产率 (78-​​94%) 得到腈。该方法同样适用于带有芳香族、杂环和脂肪族部分的醛肟和伯酰胺。方便的催化程序拓宽了环丙烯酮在有机合成中的应用范围。

  DOI：

  10.1002/ejoc.201300059
• 作为产物：
  描述：

  3-甲基噻吩醛 在 盐酸羟胺 、 sodium carbonate 作用下， 以 正己烷 、 水 为溶剂， 反应 2.0h， 生成 3-methyl-2-thiophenecarboxaldoxime
  参考文献：
  名称：

  通过串联化学-酶级联对醛类到腈类的无氰转化和酰胺的一锅法合成进行编程

  摘要：

  腈由于其多功能转化而被广泛应用于合成药物、农用化学品和材料。尽管已经开发了多种将腈基引入有机分子的方法，但其中大多数都需要使用剧毒化学品、过渡金属或苛刻的条件。在这项工作中，我们报道了一种更环保的化学酶级联反应，可以从容易获得的醛中合成烷基腈和芳基腈，并通过人工酶级联进一步转化为相应的酰胺。设计了一个双相反应系统，通过简单的相分离来桥接化学合成和酶催化。双相系统主要完美避免了羟胺对恶臭假单胞菌醛肟脱水酶的失活(OxdF1) 和来自Aurantimonas manganoxydans ATCC BAA-1229 (NHase1229) 的腈水合酶。对于各种腈的合成，通过化学-酶级联获得了大约 60% 的中等分离产率。有趣的是，在大肠杆菌细胞中，通过 OxdF1 和 NHase1229 的协同催化，脱水和水合这两个看似矛盾的反应依次进行合成酰胺。在一升规模下，苯甲酰胺的分离产率约为 62%。此

  DOI：

  10.1039/d2ra03256b

文献信息

• Cyclopropenone-Catalyzed Direct Conversion of Aldoximes and Primary Amides into Nitriles
  作者：Ankita Rai、Lal Dhar S. Yadav

  DOI：10.1002/ejoc.201300059

  日期：2013.4

  Efficient conversion of aldoximes and primary amides into nitriles by employing cyclopropenone as an organocatalyst is reported. The reaction proceeds smoothly under mild conditions with 5 mol-% catalyst loading to afford nitriles in excellent yields (78–94 %) in a single operation. This method is equally applicable to both aldoximes and primary amides bearing aromatic, heterocyclic, and aliphatic

  报道了使用环丙烯酮作为有机催化剂将醛肟和伯酰胺有效转化为腈类。反应在温和条件下顺利进行，催化剂负载量为 5 mol%，在一次操作中以优异的产率 (78-​​94%) 得到腈。该方法同样适用于带有芳香族、杂环和脂肪族部分的醛肟和伯酰胺。方便的催化程序拓宽了环丙烯酮在有机合成中的应用范围。
• Systematic Structure-Activity Relationship (SAR) Exploration of Diarylmethane Backbone and Discovery of A Highly Potent Novel Uric Acid Transporter 1 (URAT1) Inhibitor
  作者：Wenqing Cai、Jingwei Wu、Wei Liu、Yafei Xie、Yuqiang Liu、Shuo Zhang、Weiren Xu、Lida Tang、Jianwu Wang、Guilong Zhao

  DOI：10.3390/molecules23020252

  日期：——

  In order to systematically explore and better understand the structure-activity relationship (SAR) of a diarylmethane backbone in the design of potent uric acid transporter 1 (URAT1) inhibitors, 33 compounds (1a–1x and 1ha–1hi) were designed and synthesized, and their in vitro URAT1 inhibitory activities (IC50) were determined. The three-round systematic SAR exploration led to the discovery of a highly

  为了系统地探索和更好地理解二芳基甲烷骨架在设计强效尿酸转运蛋白 1 (URAT1) 抑制剂时的构效关系 (SAR)，设计并合成了 33 种化合物（1a-1x 和 1ha-1hi），并测定了它们的体外 URAT1 抑制活性 (IC50)。三轮系统的 SAR 探索导致发现了一种高效的新型 URAT1 抑制剂，1h，其效力分别比母体 lesinurad 和苯溴马隆强 200 倍和 8 倍（IC50 = 0.035 μM 对人 URAT1 1 小时 vs lesinurad 和苯溴马隆分别为 7.18 μM 和 0.28 μM）。化合物 1h 是迄今为止我们实验室发现的最有效的 URAT1 抑制剂，也可与目前正在临床试验中开发的最有效的抑制剂相媲美。
• 一种含二氢异噁唑的苯并咪唑类化合物及其 应用
  申请人：浙江工业大学

  公开号：CN104496976B

  公开（公告）日：2017-01-18

  本发明公开了一种含二氢异噁唑的苯并咪唑类化合物及其应用，所述含二氢异噁唑的苯并咪唑类化合物是式(Ⅰ)所示的1‑[3‑R‑二氢异噁唑‑5‑亚甲基]‑2‑三氟甲基‑1H‑苯并咪唑[d]，其中R取代基为取代苯基或2‑(3‑甲基噻吩)，取代苯基上的取代基为一个或多个，取代基各自独立选自下列之一：卤素、C1～C4的烷基、C1～C4的烷氧基、三氟甲基、氰基或二(C1～C2烷基)取代的氨基。所述的1‑[3‑R‑二氢异噁唑‑5‑亚甲基]‑2‑三氟甲基‑1H‑苯并咪唑[d]可应用于制备抗菌剂。本发明提供的1‑[3‑R‑二氢异噁唑‑5‑亚甲基]‑2‑三氟甲基‑1H‑苯并咪唑[d]对多种菌体菌(枯草芽孢杆菌、大肠杆菌、金黄色葡萄球菌、烟曲霉)有抑制作用，且合成工艺简单，易于产业化。
• 一种含异噁唑的苯并咪唑类化合物及其应用
  申请人：浙江工业大学

  公开号：CN104496975B

  公开（公告）日：2017-01-11

  本发明公开了一种含异噁唑的苯并咪唑类化合物及其应用，所述含异噁唑的苯并咪唑类化合物为式(Ⅰ)所示的1‑[3‑R‑异噁唑‑5‑亚甲基]‑2‑三氟甲基‑1H‑苯并咪唑[d]，其中R为取代苯基或2‑(3‑甲基噻吩)，取代苯基上的取代基为一个或多个，取代基各自独立选自卤素、C1～C4的烷基、C1～C4的烷氧基、三氟甲基或二(C1～C2烷基)取代的氨基。所述的1‑[3‑R‑异噁唑‑5‑亚甲基]‑2‑三氟甲基‑1H‑苯并咪唑[d]可用于制备抗菌剂。本发明提供的1‑[3‑R‑异噁唑‑5‑亚甲基]‑2‑三氟甲基‑1H‑苯并咪唑[d]对多种菌体菌(枯草芽孢杆菌、大肠杆菌、金黄色葡萄球菌、烟曲霉)有抑制作用，且合成工艺简单，易于产业化。
• Discovery of Natural Rosin Derivatives Containing Oxime Ester Moieties as Potential Antifungal Agents to Control Tomato Gray Mold Caused by <i>Botrytis cinerea</i>
  作者：Yanqing Gao、Renle Xu、Shihao Gu、Kun Chen、Jian Li、Xiaohua He、Shibin Shang、Zhanqian Song、Jie Song

  DOI：10.1021/acs.jafc.2c01532

  日期：2022.5.11

  series of dehydroabietyl oxime ester derivatives were synthesized using rosin as a raw material. Based on the evaluation and screening of in vitro antifungal activities against Botrytis cinerea (B. cinerea), Sclerotinia sclerotiorum, Valsa mali, Rhizoctonia solani, Fusarium oxysporum, and Alternaria alternata, compound 4f exhibited the best antifungal activity against B. cinerea, and its EC50 was 0.798

  受天然产物抗病原真菌应用的启发，以松香为原料合成了两个系列的脱氢枞基肟酯衍生物。通过对灰霉病菌、核盘菌、马里瓦尔萨、立枯病菌、尖孢镰刀菌和链格孢菌体外抗真菌活性的评价和筛选，化合物4f对灰霉病菌的抗真菌活性最好，其欧共体50为0.798 mg/L，低于阳性对照品醚菌酯（1.112 mg/L）。体内抗真菌活性结果表明，4f对番茄具有满意的保护和疗效。生理生化研究表明，化合物4f对灰霉病菌的作用机制是改变菌丝体的形态和超微结构，增加细胞膜的通透性，引起细胞核和线粒体功能障碍，从而导致细胞凋亡。此外，定性和定量构效关系研究表明，化合物4f之间的诱导和共轭相互作用与靶受体形成电子转移过程，从而达到抗真菌作用。这些结果表明，衍生自天然产物松香的化合物4f是一种新的潜在的抗灰霉病菌候选物。