4-羟苄基丙二酸二甲酯 | 51947-45-6

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 4-羟苄基丙二酸二甲酯
• 中文别名: 4-羟基二苄基丙二酸二甲酯
• 英文名称: dimethyl (4-hydroxyphenyl)methylenemalonate
• 英文别名: 2-(4-hydroxybenzylidene)malonic acid dimethyl ester；dimethyl 2-(4-hydroxybenzylidene)malonate；dimethyl 4-hydroxybenzylidenemalonate；dimethyl (p-hydroxybenzylidene)malonate；4-hydroxybenzylidene-malonic acid dimethyl ester；dimethyl para-hydroxybenzalmalonate；Dimethyl ((4-hydroxyphenyl)methylene)malonate；dimethyl 2-[(4-hydroxyphenyl)methylidene]propanedioate
• CAS: 51947-45-6
• 化学式: C₁₂H₁₂O₅
• mdl: MFCD00043985
• 分子量: 236.224
• InChiKey: SVNROXUQMHLOTA-UHFFFAOYSA-N

物化性质

• 熔点：
  155-160 °C
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2918290000
• 储存条件：
  存放于阴凉干燥处。

SDS

Name:	4-Hydroxy Benzylidene Malonic Acid Dimethyl Ester 97+% Material Safety Data Sheet
Synonym:	2-[(4-Hydroxyphenyl)methylene] Propanedioic Acid Dimethyl Ester; Dimethyl 2-[(4-Hydroxyphenyl)methylene]propane Dioate
CAS:	51947-45-6

Section 1 - Chemical Product MSDS Name:4-Hydroxy Benzylidene Malonic Acid Dimethyl Ester 97+% Material Safety Data Sheet
Synonym:2-[(4-Hydroxyphenyl)methylene] Propanedioic Acid Dimethyl Ester; Dimethyl 2-[(4-Hydroxyphenyl)methylene]propane Dioate

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
51947-45-6	4-Hydroxy Benzylidene Malonic Acid Dim	97+	257-539-1

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

---

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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. 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. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

---

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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 51947-45-6: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: yellow-green
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 157.00 - 160.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: <0.1% (20 c)
Specific Gravity/Density:
Molecular Formula: C12H12O5
Molecular Weight: 236.22

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 51947-45-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Hydroxy Benzylidene Malonic Acid Dimethyl Ester - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

---

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.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 51947-45-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 51947-45-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 51947-45-6 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-羟苄基丙二酸二甲酯 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以97%的产率得到dimethyl 4-hydroxybenzylmalonate
  参考文献：
  名称：

  螺内[4.5]癸烷结构合成生物碱和萜烯的分子内对-苯酚烯丙基化自由基环化策略

  摘要：

  该温斯腾-正宗反应的辻-特罗斯特变体已被研究用于AC螺环环系的合成9轴承的季碳在fawcettimine类型发现石松生物碱magellanine 1和lycojaponicumin乙2和cyclopiane双萜如conidiogenone 3。B环的环用于合成三环ABC芯证实利用5-外型-trig自由基伯碳基团环化到用三-产生的环己二烯酮Ñ -butylgermanium氢化物（9  →  11）。

  DOI：

  10.1016/j.tetlet.2017.07.003
• 作为产物：
  描述：

  对羟基苯甲醛 、 丙二酸二甲酯 在 哌啶鎓苯甲酸盐 作用下， 以 甲苯 为溶剂， 生成 4-羟苄基丙二酸二甲酯
  参考文献：
  名称：

  Design, Synthesis and In-vivo Hypoglycemic Evaluation of Novel Non - TZD'S in a Type - 2 Diabetic Model

  摘要：

  为了开发新型非 TZD 抗糖尿病化合物，设计了一系列异恶唑烷二酮类药物来靶向 PPAR-γ 受体。对从蛋白质数据库(2PRG)获得的罗格列酮与PPAR-γ受体的共结晶蛋白质结构进行对接研究。三个分子观察到与罗格列酮类似的相互作用；进一步合成3a、3b和3c并进行体内降血糖、总胆固醇(CHL)和甘油三酯(TG)评价。 14 天的治疗显示血糖水平显着降低，但在总 CHL 和 TG 降低效果方面并未达到理想的效果。 20 mg/kg/天的 3a、3b 和 3c 观察到的血糖降低分别为 53.96%、61.35%、61.32%，而 10mg/kg/天的标准吡格列酮则为 59.95%。

  DOI：

  10.2174/157340613804488468

文献信息

• Compounds, pharmaceutical compositions and methods for use in treating metabolic disorders
  申请人：Akerman Michelle

  公开号：US20060004012A1

  公开（公告）日：2006-01-05

  The present invention provides compounds useful, for example, for modulating insulin levels in a subject and that have the general formula Q-L 1 -P-L 2 -M-X-L 3 -A wherein the definitions of the variables Q, L 1 , P, L 2 , M, X, L 3 and A are provided herein. The present invention also provides compositions and methods for use of the compounds, for instance, for treatment of type II diabetes.

  本发明提供了一种有用的化合物，例如，用于调节受试者体内胰岛素水平的化合物，其具有以下一般公式 Q-L1-P-L2-M-X-L3-A 其中变量Q、L1、P、L2、M、X、L3和A的定义在此处提供。本发明还提供了用于这些化合物的组合物和方法，例如，用于治疗2型糖尿病。
• Quinoline derivatives and medicinal use thereof
  申请人：——

  公开号：US20030212100A1

  公开（公告）日：2003-11-13

  A quinoline derivative represented by the following formula (1): 1 allows PPAR&agr; or &ggr; which is an intranuclear transcription factor, to function strongly and is low in toxicity. By using this compound as an active ingredient, there can be provided a preventive or therapeutic agent for various diseases related to PPAR&agr; or &ggr;.

  由以下式（1）表示的喹啉衍生物，可以使作为细胞核转录因子的PPAR&agr;或&ggr;功能强大且毒性低。通过使用这种化合物作为活性成分，可以提供与PPAR&agr;或&ggr;相关的各种疾病的预防或治疗剂。
• Gadolinium triflate catalyzed alkylation of pyrroles: efficient synthesis of 3-oxo-2,3-dihydro-1H-pyrrolizine derivatives
  作者：Canan Unaleroglu、Arife Yazici

  DOI：10.1016/j.tet.2007.04.018

  日期：2007.6

  Novel 2-alkylated pyrrole derivatives were synthesized regioselectively by Gd(OTf)3 catalyzed addition reactions of pyrrole to substituted dimethyl 2-benzylidenemalonate derivatives under mild reaction conditions. 2-Alkylated pyrrole derivatives are used for the construction of the 3-oxo pyrrolizine skeleton. Intramolecular cyclization of alkylated pyrrole derivatives afforded new diastereoselective

  在温和的反应条件下，通过Gd（OTf）3催化的吡咯与取代的2-苄叉基丙二酸二甲酯的加成反应，区域选择性地合成了新型的2-烷基化吡咯衍生物。2-烷基化吡咯衍生物用于构建3-氧代吡咯嗪骨架。烷基化吡咯衍生物的分子内环化提供了新的非对映选择性的3-氧代-2,3-二氢-1 H-吡咯嗪衍生物，具有良好或高产率。
• The Most Potent Organophosphorus Inhibitors of Leucine Aminopeptidase. Structure-Based Design, Chemistry, and Activity
  作者：Jolanta Grembecka、Artur Mucha、Tomasz Cierpicki、Paweł Kafarski

  DOI：10.1021/jm030795v

  日期：2003.6.1

  phosphinate dipeptide analogues, which were synthesized and evaluated as inhibitors of the enzyme. The in vitro kinetic studies for the phosphinate dipeptide analogues revealed that these compounds belong to the group of the most effective LAP inhibitors found so far. Their further modification at the P1 position resulted in more active inhibitors, hPheP[CH(2)]Phe and hPheP[CH(2)]Tyr (K(i) values 66 nM and

  描述了一类新型的非常有效的细胞溶质亮氨酸氨基肽酶（LAP）抑制剂，该酶是金属蛋白酶家族的成员。牛晶状亮氨酸氨肽酶与亮氨酸的膦酸类似物（LeuP）配合的X射线结构用于新型LAP抑制剂的基于结构的设计，并用于分析其与酶结合位点的相互作用。通过修饰LeuP结构中的膦酸基团以寻找结合在酶S'侧的取代基来设计抑制剂。这产生了两类化合物，膦酰胺和次膦酸酯二肽类似物，它们被合成并被评估为酶的抑制剂。次膦酸酯二肽类似物的体外动力学研究表明，这些化合物属于迄今为止发现的最有效的LAP抑制剂。它们在P1位置的进一步修饰产生了更具活性的抑制剂hPheP [CH（2）] Phe和hPheP [CH（2）] Tyr（四种非对映异构体的混合物的K（i）值分别为66 nM和67 nM ）。如果考虑所有包含模拟LAP催化的反应过渡态的磷原子的化合物，则这些抑制剂对酶的结合亲和力最高。为了评估设计的LAP抑制剂的选择性，对
• Process for producing isoxazolidinedione compound
  申请人：Japan Tobacco Inc.

  公开号：US06248897B1

  公开（公告）日：2001-06-19

  The present invention relates to a novel method for producing a compound of the formula [11] wherein R is an optionally substituted aromatic hydrocarbon group, an optionally substituted alicyclic hydrocarbon group, an optionally substituted heterocyclic group or an optionally substituted condensed heterocyclic group, which is useful as a therapeutic agent for diabetes. The method of the present invention is an industrially utilizable method that enables efficient production of the objective compound [11] from &bgr;-methyl L-aspartate via an important intermediate compound [6] wherein R is as defined above, at high yield.

  本发明涉及一种生产化合物的新方法，该化合物的结构如下：其中R为可选择取代的芳香烃基、可选择取代的脂环烃基、可选择取代的杂环基或可选择取代的紧凑杂环基，该化合物可用作糖尿病的治疗剂。本发明的方法是一种工业可利用的方法，能够通过从β-甲基L-天冬氨酸经过一个重要的中间化合物（其中R如上定义）以高产率高效地生产目标化合物的方法。