1-甲基-3-丙基-1H-吡唑-5-甲酸乙酯 | 133261-07-1

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-甲基-3-丙基-1H-吡唑-5-甲酸乙酯
• 中文别名: 1-甲基-3-正丙基-吡唑-5-甲酸乙酯；1-甲基-3-丙基-1H-吡唑-5-羧酸乙酯
• 英文名称: 1-Methyl-3-n-propylpyrazole-5-carboxylic acid ethyl ester
• 英文别名: ethyl 1-methyl-3-propyl-1H-pyrazole-5-carboxylate；ethyl 1-methyl-3-n-propyl-pyrazole-5-carboxylate；ethyl 1-methyl-3-propyl-5-pyrazolecarboxylate；2-methyl-5-propyl-2H-pyrazole-3-carboxylic acid ethyl ester；ethyl 2-methyl-5-propylpyrazole-3-carboxylate
• CAS: 133261-07-1
• 化学式: C₁₀H₁₆N₂O₂
• mdl: MFCD08459062
• 分子量: 196.249
• InChiKey: ZPSRHLWRTVNGSM-UHFFFAOYSA-N

物化性质

• 沸点：
  302.0±30.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933199090
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 5-propyl-1H-pyrazole-3-carboxylate
Synonyms: Ethyl 5-propyl-2H-pyrazole-3-carboxylate

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

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Section 3. Composition/information on ingredients.
Ingredient name: Ethyl 5-propyl-1H-pyrazole-3-carboxylate
CAS number: 133261-07-1

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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.

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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.

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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.

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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, refrigerated.
Storage:

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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.

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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: C9H14N2O2
Molecular weight: 182.2

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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.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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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.

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

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1-甲基-3-丙基-1H-吡唑-5-甲酸乙酯 在 盐酸 、 氯化亚砜 、 硫酸 、 水 、 硝酸 作用下， 生成 1-methyl-4-nitro-3-propyl-1H-pyrazole-5-carbonyl chloride
  参考文献：
  名称：

  [EN] NOVEL COMPOUNDS FOR USE IN COGNITION IMPROVEMENT
  [FR] NOUVEAUX COMPOSÉS À UTILISER POUR AMÉLIORER LA COGNITION

  摘要：

  用于改善认知的新化合物。涉及具有多环结构和-(C=O)NRaRb基团的某些化合物，其中多环结构包括至少三个环系统，其中一个环系统是包含2至4个环的多环环系统；至少一个环是芳香环；结构中包含至少3个氮原子和1个氧原子。还涉及含有它们的药物组合物，以及它们在医学中的使用，特别是在治疗和/或预防伴有认知缺陷或损害的神经系统疾病或神经退行性疾病中的使用。

  公开号：

  WO2016020307A1
• 作为产物：
  描述：

  3-正丙基吡唑-5-甲酸乙酯 以79的产率得到1-甲基-3-丙基-1H-吡唑-5-甲酸乙酯
  参考文献：
  名称：

  Pyrazolopyrimidinone antianginal agents

  摘要：

  该化合物的分子式为：##STR1## 其中R.sup.1是H，C.sub.1 -C.sub.3烷基，C.sub.3 -C.sub.5环烷基或C.sub.1 -C.sub.3全氟烷基；R.sup.2是H，C.sub.1 -C.sub.6烷基，可选择性地被OH取代，C.sub.1 -C.sub.3烷氧基或C.sub.3 -C.sub.6环烷基，或C.sub.1 -C.sub.3全氟烷基；R.sup.3是C.sub.1 -C.sub.6烷基，C.sub.3 -C.sub.6烯基，C.sub.3 -C.sub.6炔基，C.sub.3 -C.sub.7环烷基，C.sub.1 -C.sub.6全氟烷基或(C.sub.3 -C.sub.6环烷基)C.sub.1 -C.sub.6烷基；R.sup.4与其所连接的氮原子共同形成吡咯烷基，哌啶基，吗啉基或4-N-(R.sup.6)-哌嗪基团；R.sup.5是H，C.sub.1 -C.sub.4烷基，C.sub.1 -C.sub.3烷氧基，NR.sup.7 R.sup.8或CONR.sup.7 R.sup.8；R.sup.6是H，C.sub.1 -C.sub.6烷基，(C.sub.1 -C.sub.3烷氧基)C.sub.2 -C.sub.6烷基，羟基C.sub.2 -C.sub.6烷基，(R.sup.7 R.sup.8 N)C.sub.2 -C.sub.6烷基，(R.sup.7 R.sup.8 NCO)C.sub.1 -C.sub.6烷基，CONR.sup.7 R.sup.8，CSNR.sup.7 R.sup.8或C(NH)NR.sup.7 R.sup.8；R.sup.7和R.sup.8各自独立地是H，C.sub.1 -C.sub.4烷基，(C.sub.1 -C.sub.3烷氧基)C.sub.2 -C.sub.4烷基或羟基C.sub.2 -C.sub.4烷基；以及其药学上可接受的盐，是选择性cGMP PDE抑制剂，用于治疗心血管疾病，如心绞痛，高血压，心力衰竭和动脉粥样硬化。

  公开号：

  US05250534A1
• 作为试剂：
  描述：

  sodium ethanolate 、 2-戊酮 、 草酸二乙酯 、 甲基肼 、 、 在 initial mixture 、 ester enolate 、 甲酸 、 乙醇 、 甲苯 、 水 、 1-甲基-3-丙基-1H-吡唑-5-甲酸乙酯 、 1-甲基-5-丙基-1H-吡唑-3-甲酸乙酯 作用下， 以 乙醇 、 甲苯 、 水 、 甲酸 为溶剂， 反应 2.25h， 以98 g of the desired product were obtained in a purity of 98.9% by weight (determined by gas chromatography)的产率得到1-甲基-3-丙基-1H-吡唑-5-甲酸乙酯
  参考文献：
  名称：

  Process for the preparation of 1-alkyl-pyrazole-5-carboxylic acid esters

  摘要：

  1-烷基吡唑-5-羧酸酯是通过在溶剂存在下，将2,4-二酮羧酸酯的烯醇酸根与N-烷基肼盐反应制备而成。该过程以简单的方式特别经济地制备1-烷基吡唑-5-羧酸酯，并且只会产生少量不良异构体。

  公开号：

  US05977378A1

文献信息

• HIGHLY SELECTIVE and LONG-ACTING PDE5 MODULATORS
  申请人：Gant Thomas G.

  公开号：US20080194529A1

  公开（公告）日：2008-08-14

  Disclosed herein are substituted phosphodiesterase type 5 enzyme modulators of Formula I, processes of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.

  披露的是式I的取代的磷酸二酯酶5型酶调节剂，其制备过程，药物组合物及其用途。
• Comparison of different heterocyclic scaffolds as substrate analog PDE5 inhibitors
  作者：Helmut Haning、Ulrich Niewöhner、Thomas Schenke、Thomas Lampe、Alexander Hillisch、Erwin Bischoff

  DOI：10.1016/j.bmcl.2005.05.090

  日期：2005.9

  Several different heterocyclic systems were compared as PDE5 inhibitor scaffolds. In addition to the known 3H-imidazo[5,1-f][1,2,4]triazin-4-ones and pyrazolopyrimidinones, isomeric imidazo[1,5-a][1,3,5]triazin-4(3H)-ones were also shown to be potent and selective PDE inhibitor scaffolds with in vivo activity. SAR trends were elucidated for sulfonamide derivatives with generality across different scaffolds

  比较了几种不同的杂环系统作为PDE5抑制剂支架。除了已知的3H-咪唑并[5,1-f] [1,2,4]三嗪-4-酮和吡唑并吡喃二酮外，咪唑并[1,5-a] [1,3,5]三嗪-4（ 3H）-一也被证明是具有体内活性的有效的和选择性的PDE抑制剂支架。阐明了在不同支架上具有普遍性的磺酰胺衍生物的SAR趋势。
• Method of treating a patient having precancerous lesions with phenyl purinone derivatives
  申请人：Cell Pathways, Inc.

  公开号：US06200980B1

  公开（公告）日：2001-03-13

  Derivatives of Phenyl Purinone are useful for the treatment of patients having precancerous lesions. These compounds are also useful to inhibit growth of neoplastic cells.

  苯基嘌呤酮衍生物对于治疗患有癌前病变的患者非常有用。这些化合物还可用于抑制肿瘤细胞的生长。
• Pyrazolopyrimidinone cGMP PDE5 inhibitors for the treatment of sexual dysfunction
  申请人：Pfizer Inc.

  公开号：US06251904B1

  公开（公告）日：2001-06-26

  Compounds of the formulae (IA) and (IB): wherein R1 is C1 to C3 alkyl optionally substituted with phenyl, Het or a N-linked heterocyclic group selected from piperidinyl and morpholinyl; wherein said phenyl group is optionally substituted by one or more substitutents selected from C1 to C4 alkoxy; halo; CN; CF3; OCF3 or C1 to C4 alkyl wherein said C1 to C4 alkyl group is optionally substituted by C1 to C4 haloalkyl or haloalkoxy either of which is substituted by one or more halo atoms; R2 is C1 to C6 alkyl and R13 is OR3 or NR5R6, or pharmaceutically or veterinarily acceptable salts thereof, or pharmaceutically or veterinarily acceptable solvates of either entity are potent and selective inhibitors of type 5 cyclic guanosine 3′,5′-monophosphate phosphodiesterase (cGMP PDE5) and have utility in the treatment of, inter alia, male erectile dysfunction (MED) and female sexual dysfunction (FSD).

  化合物的化学式（IA）和（IB）：其中R1是C1到C3烷基，可选择地被苯基、Het或从哌啶基和吗啉基中选择的N-连接的杂环基取代；其中所述苯基可选择地被来自C1到C4烷氧基、卤素、氰基、三氟甲基、三氟乙氧基或从C1到C4烷基中选择的一个或多个取代基取代，其中所述C1到C4烷基可选择地被C1到C4卤代烷基或卤代氧基取代，其中任一者被一个或多个卤原子取代；R2是C1到C6烷基，R13是OR3或NR5R6，或它们的药学或兽医学上可接受的盐，或者它们的药学或兽医学上可接受的溶剂，是强效且选择性的5′-环磷酸鸟苷3′,5′-单磷酸酯酶（cGMP PDE5）抑制剂，并在治疗男性勃起功能障碍（MED）和女性性功能障碍（FSD）等方面具有用途。
• [EN] PYRAZOLOPYRIMIDINONES FOR THE TREATMENT OF IMPOTENCE AND PROCESS FOR THE PREPARATION THEREOF<br/>[FR] PYRAZOLOPYRIMIDINONES POUR LE TRAITEMENT DE L'IMPUISSANCE ET PROCÉDÉ DE PRÉPARATION CORRESPONDANT
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2015114647A1

  公开（公告）日：2015-08-06

  The present invention relates to Pyrazolopyrimidinone compounds as PDE5 inhibitors with better IC50 value, good in vivo efficacy and PK profile and a process for the preparation thereof. The present invention covers the pyrazolo pyrimidinone based compounds that have been designed, synthesized and screened for PDE5 inhibitory activity and its PDE5 inhibitory potential is provided in this invention. These designer compounds have shown nanomolar potency when screened for PDE5 inhibitory activity and also shown better in vivo efficacy. These compounds can be used in the treatment of male erectile dysfunction or in the treatment of impotence.

  本发明涉及作为PDE5抑制剂的吡唑嘧啶酮化合物，具有更好的IC50值、良好的体内有效性和PK特性，以及其制备方法。本发明涵盖基于吡唑嘧啶酮的化合物，这些化合物已经被设计、合成和筛选用于PDE5抑制活性，其PDE5抑制潜力在本发明中提供。这些设计的化合物在筛选PDE5抑制活性时表现出纳摩尔级的效力，并且在体内表现出更好的有效性。这些化合物可以用于治疗男性勃起功能障碍或阳痿的治疗。