3-乙氧基苯甲酸甲酯 | 108593-47-1

• 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: 3-乙氧基苯甲酸甲酯
• 英文名称: methyl 3-ethoxybenzoate
• CAS: 108593-47-1
• 化学式: C₁₀H₁₂O₃
• mdl: MFCD00017263
• 分子量: 180.203
• InChiKey: IFLQNIVRGRISMD-UHFFFAOYSA-N

物化性质

• 沸点：
  100°C 2mm
• 密度：
  1.073±0.06 g/cm3(Predicted)
• 闪点：
  100°C/2mm
• 保留指数：
  1427
• 稳定性/保质期：

  常温常压下稳定，避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2918990090
• 危险性防范说明：
  P261,P301+P312,P302+P352,P304+P340,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  密封存储于阴凉、干燥的库房，并远离氧化剂。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Methyl 3-ethoxybenzoate
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: Methyl 3-ethoxybenzoate
CAS number: 108593-47-1

---

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: C10H12O3
Molecular weight: 180.2

---

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

---

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-乙氧基苯甲酸甲酯 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 生成 3-乙氧基苯酰肼
  参考文献：
  名称：

  Discovery of Acylsulfonohydrazide-Derived Inhibitors of the Lysine Acetyltransferase, KAT6A, as Potent Senescence-Inducing Anti-Cancer Agents

  摘要：

  A high-throughput screen designed to discover new inhibitors of histone acetyltransferase KAT6A uncovered CTX-0124143 (1), a unique aryl acylsulfonohydrazide with an IC50 of 1.0 mu M. Using this acylsulfonohydrazide as a template, we herein disclose the results of our extensive structure-activity relationship investigations, which resulted in the discovery of advanced compounds such as 55 and 80. These two compounds represent significant improvements on our recently reported prototypical lead WM-8014 (3) as they are not only equivalently potent as inhibitors of KAT6A but are less lipophilic and significantly more stable to microsomal degradation. Furthermore, during this process, we discovered a distinct structural subclass that contains key 2-fluorobenzenesulfonyl and phenylpyridine motifs, culminating in the discovery of WM-1119 (4). This compound is a highly potent KAT6A inhibitor (IC50 = 6.3 nM; K-D = 0.002 mu M), competes with Ac-CoA by binding to the Ac-CoA binding site, and has an oral bioavailability of 56% in rats.

  DOI：

  10.1021/acs.jmedchem.9b02071
• 作为产物：
  描述：

  氯乙烷 、 3-羟基苯甲酸甲酯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 3-乙氧基苯甲酸甲酯
  参考文献：
  名称：

  新型3-苯甲酰胺基苯甲酸衍生物作为法呢类X受体部分激动剂的设计，合成和生物学研究

  摘要：

  法尼醇X受体（FXR）是胆汁酸激活的核受体，调节胆汁酸和脂质的代谢，并维持内部环境的稳定性。FXR被认为是肝脏疾病（如药物性肝损伤，脂肪肝和胆汁淤积症）的治疗目标。先前报道的FXR部分激动剂6就其高强度和低分子大小而言是一种合适的先导化合物，而化合物6的对接研究则显示了一个较大的未占据的疏水口袋，这可能为结构活性关系提供了更多可能性（SAR ）学习。在这项研究中，我们基于铅化合物6进行了全面的SAR和分子建模研究。所有这些努力导致鉴定出一系列新的FXR部分激动剂。在该系列中，化合物41表现出最佳的活性，并且与FXR的结合口袋有很强的相互作用。此外，化合物41通过调节FXR相关基因的表达并提高抗氧化能力，保护小鼠免受对乙酰氨基酚诱导的肝毒性。总之，这些结果表明化合物41是一种有前途的FXR部分激动剂，适合进一步研究。

  DOI：

  10.1016/j.ejmech.2020.113106

文献信息

• Correlation of carbon-13 substituent-induced chemical shifts:Meta- andpara-substituted methyl benzoates
  作者：Miloš Buděšńský、Otto Exner

  DOI：10.1002/mrc.1260270612

  日期：1989.6

  Carbon‐13 NMR spectra are reported for 69 substituted methyl benzoates in deuteriochloroform or in its mixture with dimethyl sulphoxide‐d6. The substituent‐induced chemical shifts (SCS) of the CO carbon correlate poorly with dual substituent parameters (DSP) in all possible modifications, and for meta derivatives in particular this correlation is both overpara meterized and imprecise. A much better

  69 取代的苯甲酸甲酯在氘代氯仿中或其与二甲基亚砜-d6 的混合物中的碳 13 NMR 谱报告。在所有可能的修饰中，CO 碳的取代基诱导化学位移 (SCS) 与双取代基参数 (DSP) 的相关性很差，特别是对于间位衍生物，这种相关性既过度参数化又不精确。先前通过主成分分析 (PCA) 从更大的集合中导出的参数（指定为 Bm、Bp 和 Cp）获得了更好的相关性。CH3 碳的 SCS 与原始的简单哈米特方程非常相关，不需要 DSP 处理。在如此大的集合中，取代基的聚类并不重要。
• Product distribution in the metalation of some aromatic substrates with n-butyllithium
  作者：David A. Shirley、James R. Johnson、John P. Hendrix

  DOI：10.1016/0022-328x(68)80043-9

  日期：——

  The following compounds were metalated with n-butyllithium in ether and product isomer ratios determined with the aid of vapor phase chromatographic techniques: anisole, trifluoromethylbenzene, phenetole, m-cresol methyl ether, resorcinol dimethyl ether and biphenyl. The data with all substrates except biphenyl are in accord with the view of relative rate of attack of different ring positions controlled

  苯甲醚，三氟甲苯，苯乙醚，：下面的化合物用在醚中的正丁基锂和产物异构体用的气相色谱技术辅助确定比金属化米甲酚甲基醚，间苯二酚二甲醚和联苯基。除联苯外，所有底物的数据均符合不同环位置的相对进攻速率的观点，该相对位置的进攻速率受环取代基对环碳氢键“酸度”的感应影响所控制。
• Loss of benzene to generate an enolate anion by a site-specific double-hydrogen transfer during CID fragmentation of<i>o</i>-alkyl ethers of<i>ortho</i>-hydroxybenzoic acids
  作者：Athula B. Attygalle、Jason B. Bialecki、Upul Nishshanka、Carl S. Weisbecker、Josef Ruzicka

  DOI：10.1002/jms.1399

  日期：2008.9

  isomers showed peaks at m/z 77 for the phenyl anion and m/z 93 for the phenoxyl anion, in addition to that for the ortho-specific enolate anion. Under high collision energy, the ortho isomers also produce a peak at m/z 137 for an alkene loss. The spectra of meta and para compounds show a peak at m/z 92 for the distonic anion produced by the homolysis of the O-C bond. Moreover, a small peak at m/z 136 for

  碰撞诱导的衍生自邻烷氧基苯甲酸的阴离子的解离提供了一种生产气态烯醇式阴离子的简便方法。最初损失CO（2）后产生的烷氧基苯基阴离子通过邻位异构体所特有的双氢转移机理消除了苯分子，从而形成了烯醇式阴离子。氘标记研究证实，苯损失中转移的两个氢原子起源于烷基链的位置1和2。氢原子从C-1位置的初始转移形成了苯基阴离子和羰基化合物，两者均以离子/中性络合物的形式紧密结合。通过消除中性羰基化合物，该络合物要么直接断裂以生成苯基阴离子，或通过从C-2位置转移氢原子并在此过程中消除苯分子而形成烯酸酯阴离子。与将氘原子从C-2位置转移相比，当氘原子从C-1位置转移时观察到的明显的主要动力学同位素效应表明，第一次转移是速率确定步骤。量子力学计算表明，苯的中性损失是热力学上有利的过程。在所使用的条件下，除了邻位特异性烯醇根阴离子外，仅邻位异构体的光谱在m / z 77处显示出苯基阴离子峰，在苯氧基阴离子中显示出m
• Synthesis and Evaluation of 4-Hydroxyphenylacetic Acid Amides and 4-Hydroxycinnamamides as Antioxidants
  作者：Young-Sik Jung、Tae-Souk Kang、Joong-Ho Yoon、Bo-Young Joe、Hee-Jong Lim、Churl-Min Seong、Woo-Kyu Park、Jae-Yang Kong、Jungsook Cho、No-Sang Park

  DOI：10.1016/s0960-894x(02)00479-1

  日期：2002.9

  acid amides and 4-hydroxycinnamamides were synthesized and their antioxidant and neuroprotective activities were evaluated. Among the prepared compounds, 8b, and exhibited potent inhibition of lipid peroxidation in rat brain homogenates, and marked DPPH radical scavenging activities. Furthermore, and exhibited neuroprotective action against the oxidative damage induced by the exposure of primary cultured

  合成了4-羟基苯基乙酸酰胺和4-羟基肉桂酰胺，并评估了它们的抗氧化和神经保护活性。在制备的化合物中，8b在大鼠脑匀浆中显示出对脂质过氧化的有效抑制作用，并具有明显的DPPH自由基清除活性。此外，并表现出针对主要培养的大鼠皮层细胞暴露于H（2）O（2），黄嘌呤/黄嘌呤氧化酶或Fe（2 +）/抗坏血酸引起的氧化损伤的神经保护作用。根据这些结果，我们发现它是所测试化合物中最有效的抗氧化剂。
• 3-SUBSTITUTED-6-ARYL PYRIDINES
  申请人：Hutchinson Alan J.

  公开号：US20110281837A1

  公开（公告）日：2011-11-17

  3-substituted-6-aryl pyridines of Formula I are provided: wherein R 1 , R 2 , R 3 , R 8 , R 9 , A and Ar are defined herein. Such compounds are ligands of C5a receptors. Preferred compounds of Formula I bind to C5a receptors with high affinity and exhibit neutral antagonist or inverse agonist activity at C5a receptors. The present invention also relates to pharmaceutical compositions comprising such compounds, and to the use of such compounds in treating a variety of inflammatory, cardiovascular, and immune system disorders. In addition, the present invention provides labeled 3-substituted-6-aryl pyridines, which are useful as probes for the localization of C5a receptors.

  本发明提供了式I的3-取代-6-芳基吡啶化合物：其中R1、R2、R3、R8、R9、A和Ar的定义在此处。这些化合物是C5a受体的配体。式I的优选化合物具有高亲和力结合到C5a受体，并在C5a受体上表现出中性拮抗剂或反向激动剂活性。本发明还涉及包含这些化合物的制药组合物，以及将这些化合物用于治疗各种炎症、心血管和免疫系统疾病的用途。此外，本发明提供了标记的3-取代-6-芳基吡啶，可用作C5a受体定位的探针。

表征谱图