1-(2-甲氧基苯基)-5-氧代-3-吡咯烷羧酸 | 39629-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-(2-甲氧基苯基)-5-氧代-3-吡咯烷羧酸
• 中文别名: 1-(2-甲氧苯基)-5-氧代吡咯烷-3-羧酸
• 英文名称: 1-(2-methoxyphenyl)-5-oxopyrrolidine-3-carboxylic acid
• 英文别名: 1-(2-methoxy-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid；1-(2-Methoxy-phenyl)-5-oxo-pyrrolidin-3-carbonsaeure
• CAS: 39629-90-8
• 化学式: C₁₂H₁₃NO₄
• mdl: MFCD03724918
• 分子量: 235.24
• InChiKey: BQQBMILQUDEPIK-UHFFFAOYSA-N

物化性质

• 熔点：
  165 °C
• 沸点：
  523.5±45.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933790090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-(2-Methoxyphenyl)-5-oxopyrrolidine-3-carboxylic acid
Synonyms: 1-(2-Methoxyphenyl)-2-pyrrolidinone-4-carboxylic acid

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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: 1-(2-Methoxyphenyl)-5-oxopyrrolidine-3-carboxylic acid
CAS number: 39629-90-8

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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.
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: C12H13NO4
Molecular weight: 235.2

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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-(2-甲氧基苯基)-5-氧代-3-吡咯烷羧酸 在 palladium on activated charcoal 劳森试剂 、 lithium aluminium tetrahydride 、 氯化亚砜 、 ammonium formate 、 potassium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.5h， 生成 1-{3-[6-(2-methoxyphenyl)-3,6-diazabicyclo[3.2.1]oct-3-yl]propyl}-4,4-dimethyl-piperidine-2,6-dione
  参考文献：
  名称：

  3,6-二氮杂双环[3.2.1]辛烷的一般有效合成

  摘要：

  N 6取代的3,6-二氮杂双环[3.2.1]辛烷（6a – c）的合成方便高效，从适当取代的内酰胺开始，将其转化为亚硝胺，然后进行还原环化，得到3,6-重氮二氮杂双环[3.2.1]辛烷-2-酮。然后将这些双环内酰胺还原为相应的3,6-二氮杂双环[3.2.1]辛烷，并转化为所需的N 3，N 6-双取代的3,6-二氮杂双环[3.2.1]辛烷（7a – h），筛选α 1 -肾上腺素受体拮抗活性。

  DOI：

  10.1016/j.tet.2006.02.030
• 作为产物：
  描述：

  衣康酸 、 邻甲氧基苯胺 生成 1-(2-甲氧基苯基)-5-氧代-3-吡咯烷羧酸
  参考文献：
  名称：

  N-Aryl pyrrolidinonyl oxadiazoles as potent mGluR5 positive allosteric modulators

  摘要：

  A novel series of N-aryl pyrrolidinonyl oxadiazoles were identified as mGluR5 positive allosteric modulators (PAMs). Optimization of the initial lead compound 6a led to the identification of the 12c (-) enantiomer as a potent compound with acceptable in vitro clearance, CYP, hERG and PK properties. Para substituted N-aryl pyrrolidinonyl oxadiazoles are mGluR5 PAMs while the meta and ortho substituted N-aryl pyrrolidinonyl oxadiazoles are negative allosteric modulators (NAMs). Para fluoro substitution on the N-aryl group and meta chloro or methyl substituents on the aryl oxadiazole moiety are optimal for mGluR5 PAM efficacy. The existence of an exquisitely sensitive 'PAM to NAM switch' within this chemotype making it challenging for simultaneous optimization of potency and drug-like properties. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.094

文献信息

• The Reaction of Itaconic Acid with Primary Amines
  作者：Peter L. Paytash、Edward Sparrow、Joseph C. Gathe

  DOI：10.1021/ja01159a520

  日期：1950.3
• N-Aryl pyrrolidinonyl oxadiazoles as potent mGluR5 positive allosteric modulators
  作者：Mathivanan Packiarajan、Christine G. Mazza Ferreira、Sang-Phyo Hong、Andrew D. White、Gamini Chandrasena、Xiaosui Pu、Robbin M. Brodbeck、Albert J. Robichaud

  DOI：10.1016/j.bmcl.2012.06.094

  日期：2012.9

  A novel series of N-aryl pyrrolidinonyl oxadiazoles were identified as mGluR5 positive allosteric modulators (PAMs). Optimization of the initial lead compound 6a led to the identification of the 12c (-) enantiomer as a potent compound with acceptable in vitro clearance, CYP, hERG and PK properties. Para substituted N-aryl pyrrolidinonyl oxadiazoles are mGluR5 PAMs while the meta and ortho substituted N-aryl pyrrolidinonyl oxadiazoles are negative allosteric modulators (NAMs). Para fluoro substitution on the N-aryl group and meta chloro or methyl substituents on the aryl oxadiazole moiety are optimal for mGluR5 PAM efficacy. The existence of an exquisitely sensitive 'PAM to NAM switch' within this chemotype making it challenging for simultaneous optimization of potency and drug-like properties. (C) 2012 Elsevier Ltd. All rights reserved.
• A general and efficient synthesis of 3,6-diazabicyclo[3.2.1]octanes
  作者：Rakesh K. Singh、Sanjay Jain、Neelima Sinha、Anita Mehta、Fehmida Naqvi、Nitya Anand

  DOI：10.1016/j.tet.2006.02.030

  日期：2006.4

  A convenient and efficient synthesis of N6-substituted 3,6-diazabicyclo[3.2.1]octanes (6a–c) has been achieved starting from suitably substituted lactams, which were converted to nitroenamines followed by reductive cyclization to afford 3,6-diazabicyclo[3.2.1]octane-2-ones in good yields. These bicyclic lactams were then reduced to the corresponding 3,6-diazabicyclo[3.2.1]octanes and converted to the

  N 6取代的3,6-二氮杂双环[3.2.1]辛烷（6a – c）的合成方便高效，从适当取代的内酰胺开始，将其转化为亚硝胺，然后进行还原环化，得到3,6-重氮二氮杂双环[3.2.1]辛烷-2-酮。然后将这些双环内酰胺还原为相应的3,6-二氮杂双环[3.2.1]辛烷，并转化为所需的N 3，N 6-双取代的3,6-二氮杂双环[3.2.1]辛烷（7a – h），筛选α 1 -肾上腺素受体拮抗活性。