2-(4-氟苯基)吡咯烷 | 72216-06-9

• 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: 2-(4-氟苯基)吡咯烷
• 中文别名: 2-(4-氟苯基)-吡咯烷
• 英文名称: 2-(4-fluorophenyl)pyrrolidine
• CAS: 72216-06-9
• 化学式: C₁₀H₁₂FN
• mdl: MFCD02663411
• 分子量: 165.21
• InChiKey: ZDCXMSDSTZZWAX-UHFFFAOYSA-N

物化性质

• 沸点：
  235.5±33.0 °C(Predicted)
• 密度：
  1.078±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(4-Fluorophenyl)pyrrolidine
Synonyms:

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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: 2-(4-Fluorophenyl)pyrrolidine
CAS number: 72216-06-9

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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: C10H12FN
Molecular weight: 165.2

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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, hydrogen fluoride.

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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：

  2-(4-氟苯基)吡咯烷 在 tris-(dibenzylideneacetone)dipalladium(0) 、 2-(二环己基膦基)联苯 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 23.17h， 生成 4-[2-(4-fluoro-phenyl)-pyrrolidin-1-yl]-pyridin-2-ylamine
  参考文献：
  名称：

  [EN] PYRIDYL UREAS AS MINERALOCORTICOID RECEPTOR ANTAGONISTS
  [FR] URÉES DE PYRIDYL COMME ANTAGONISTES DE RÉCEPTEUR MINÉRALOCORTICOÏDE

  摘要：

  矿物皮质激素受体拮抗剂，其中公式（1）是示例。

  公开号：

  WO2012064631A1
• 作为产物：
  描述：

  5-(4-fluorophenyl)-3,4-dihydro-2H-pyrrole 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 2.0h， 生成 2-(4-氟苯基)吡咯烷
  参考文献：
  名称：

  使用亚胺还原酶的药物相关手性2-芳基取代的吡咯烷的立体互补合成。

  摘要：

  探索天然存在的亚胺还原酶（IRED）的集合，确定了两个立体互补的IRED，它们对位阻2-芳基取代的吡咯啉的活性降低。使用（R）选择性ScIR和（S）选择性SvIR，以良好的收率（60-80％）立体互补合成了各种具有优异对映选择性（> 99％ee）的手性2-芳基取代的吡咯烷，证明了IRED的可行性用于产生药学上相关的手性2-芳基取代的吡咯烷中间体。

  DOI：

  10.1021/acs.orglett.0c00802
• 作为试剂：
  描述：

  2-(4-氟苯基)吡咯烷 、 7-(3,4-Dichlorophenyl)-4,7-dihydro-5-methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid 在 2-(4-氟苯基)吡咯烷 作用下， 生成 1-[[7-(3,4-Dichloro-phenyl)-4,7-dihydro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]carbonyl]-2-(4-fluoro-phenyl)pyrrolidine
  参考文献：
  名称：

  Heterocyclic dihydropyrimidine compounds

  摘要：

  新型杂环二氢嘧啶化合物，可用作钾通道功能抑制剂（特别是Kv1亚家族电压门控K+通道的抑制剂，特别是Kv1.5抑制剂，该抑制剂已与超快速激活延迟整流K+电流IKur相关联），使用这种化合物预防和治疗心律失常和IKur相关疾病的方法，以及含有这种化合物的药物组合物。

  公开号：

  US06706720B2

文献信息

• Palladium-catalyzed ortho-olefination of 2-arylpyrrolidines: A tool for increasing structural complexity in nitrogen heterocycles
  作者：Pablo D. Legarda、Alfonso García-Rubia、Ramón Gómez Arrayás、Juan C. Carretero

  DOI：10.1016/j.tet.2018.05.076

  日期：2018.7

  of the (2-pyridyl)sulfonyl unit as directing functionality and readily removable N-protecting group has enabled an efficient and practical transformation of 2-arylpyrrolidine derivatives into more complex tricyclic frameworks via palladium-catalyzed ortho-olefination with electron deficient alkenes and subsequent cyclization upon N-deprotection under mild conditions. The key cross coupling step in the

  （2-吡啶基）磺酰基单元作为直接官能团和易于除去的N-保护基团的双重作用使得能够通过钯催化的与缺电子烯烃的邻位烯烃化反应将2-芳基吡咯烷衍生物有效而实用地转化为更复杂的三环骨架。和随后在温和条件下在N-脱保护下环化。在三氟甲磺酸N-氟-2,4,6-三甲基吡啶鎓（[F +]）的存在下，关键的交叉偶联步骤既高效又可耐受两个偶联伙伴处的各种空间和电子变化。通过的还原条件适当选择，Ñ-磺酰基脱保护基可以选择性地形成苯并-稠合的吡咯烷或稠合的吡咯烷基-苯并氮杂framework骨架。
• [EN] SUBSTITUTED PYRAZOLO[1,5-A]PYRIDINE COMPOUNDS AS RET KINASE INHIBITORS<br/>[FR] COMPOSÉS SUBSTITUÉS DE PYRAZOLO[1,5-A]PYRIDINES COMME INHIBITEURS DE LA KINASE RET
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2017011776A1

  公开（公告）日：2017-01-19

  Provided herein are compounds of the General Formula I: and stereoisomers and pharmaceutically acceptable salts or solvates thereof, in which A, B, D, E, X1, X2, X3 and X4 have the meanings given in the specification, which are inhibitors of RET kinase and are useful in the treatment and prevention of diseases which can be treated with a RET kinase inhibitor, including diseases or disorders mediated by a RET kinase.

  本文提供了一般式I的化合物及其立体异构体和药用可接受的盐或溶剂，其中A、B、D、E、X1、X2、X3和X4的含义如规范中所述，这些化合物是RET激酶的抑制剂，可用于治疗和预防可以用RET激酶抑制剂治疗的疾病，包括由RET激酶介导的疾病或紊乱。
• NOVEL INHIBITORS
  申请人：Heiser Ulrich

  公开号：US20110092501A1

  公开（公告）日：2011-04-21

  The invention relates to novel pyrrolidine derivatives of formula (I): wherein R 1 , R 2 and R 3 are as defined herein, as inhibitors of glutaminyl cyclase (QC, EC 2.3.2.5). QC catalyzes the intramolecular cyclization of N-terminal glutamine residues into pyroglutamic acid (5-oxo-prolyl, pGlu*) under liberation of ammonia and the intramolecular cyclization of N-terminal glutamate residues into pyroglutamic acid under liberation of water.

  本发明涉及新颖的吡咯烷衍生物，其具有如下公式(I)：其中R1、R2和R3如本文所述定义，作为谷氨酰胺环化酶（QC，EC 2.3.2.5）的抑制剂。谷氨酰胺环化酶催化N末端谷氨酰胺残基形成焦谷氨酸（5-氧代脯氨酸，pGlu*）的分子内环化，并释放氨，以及催化N末端谷氨酸残基形成焦谷氨酸的分子内环化，并释放水。
• A General Approach to Stereospecific Cross-Coupling Reactions of Nitrogen-Containing Stereocenters
  作者：Xinghua Ma、Haoran Zhao、Meruyert Binayeva、Glenn Ralph、Mohamed Diane、Shibin Zhao、Chao-Yuan Wang、Mark R. Biscoe

  DOI：10.1016/j.chempr.2020.02.002

  日期：2020.3

  A novel strategy employing cyclohexyl spectator ligands in Stille cross-coupling reactions has been developed as a general solution to the long-standing challenge of conducting stereospecific cross-coupling reactions at nitrogen-containing stereocenters. This method enables direct access to enantioenriched products that are difficult (or impossible) to obtain via alternative preparative methods. Selective

  作为在含氮立体中心进行立体定向交叉偶联反应的长期挑战的常规解决方案，已开发出在Stille交叉偶联反应中采用环己基旁观者配体的新策略。该方法使得能够直接获得难以（或不可能）通过替代制备方法获得的对映体富集的产品。在利用活化的和未活化的烷基单元之间的细微电子差异的反应条件下，可以实现单个仲烷基单元的选择性和可预测的转移。通过这种方法，在所有研究的实例中，对映体富集的α-甲锡烷基化的含氮立体中心都经历了Pd催化的芳构化和酰化反应，并具有极高的立体保真度。我们通过立体定向反应中使用α-苯乙烯基吡咯烷，氮杂环丁烷和开链（苄基和非苄基）亲核试剂来证明这一过程。该过程将有助于快速可靠地获得具有氮取代的立体中心的对映体富集的化合物，该化合物在从药物发现过程中出现的生物活性化合物中构成普遍存在的结构基序。
• Hydrogen bond directed aerobic oxidation of amines <i>via</i> photoredox catalysis
  作者：Hongyu Wang、Yunquan Man、Kaiye Wang、Xiuyan Wan、Lili Tong、Na Li、Bo Tang

  DOI：10.1039/c8cc06603e

  日期：——

  An application of H-bonding interactions for directing the α-C–H oxidation of amines to amides and amino-ketones catalyzed by an organic photocatalyst is reported. The high efficiency of this method is demonstrated by the aerobic oxidation of pyrrolidines, diarylamines and benzylamines bearing urea groups with high yields and a wide substrate scope.

  据报道，在有机光催化剂的催化下，H键相互作用可指导胺的α-C–H氧化为酰胺和氨基酮。带有脲基团的吡咯烷，二芳基胺和苄基胺的好氧氧化具有高收率和广泛的底物范围，证明了该方法的高效率。