1-Boc-3-氰基-4-吡咯烷酮 | 175463-32-8

• 物质功能分类: 有机原料 - 杂环化合物
• 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-Boc-3-氰基-4-吡咯烷酮
• 中文别名: 1-BOC-3-氰基-4-吡咯烷；4-氰基-1-N-(叔丁氧羰基)吡咯烷-3-酮；1-N-叔丁氧羰基-4-氰基-3-吡咯烷酮；1-N-Boc-3-氰基-吡咯烷酮-4；1-N-BOC-3-氰基-吡咯烷酮；3-氰基-4-氧代吡咯烷-1-甲酸叔丁酯；4-氧-3-氰基-1-N-BOC-吡咯烷；1-N-Boc-3-氰基-4-吡咯烷酮；3-氰-4-吡咯烷酮；1-Boc-3-氰-4-吡咯烷酮；1-N-BOC-3-氰基-4-吡咯烷酮
• 英文名称: tert-butyl 3-cyano-4-oxopyrrolidine-1-carboxylate
• 英文别名: 1-(N-tert-butoxycarbonyl)-4-cyanopyrrolidine-3-one；N-tert-butoxycarbonyl-4-cyano-3-pyrrolidone
• CAS: 175463-32-8
• 化学式: C₁₀H₁₄N₂O₃
• mdl: MFCD01318456
• 分子量: 210.233
• InChiKey: RKUQLKRPWWYRIG-UHFFFAOYSA-N

物化性质

• 熔点：
  160-167°C
• 沸点：
  360.7±42.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)
• LogP：
  1.11 at 20℃
• 稳定性/保质期：
  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  70.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  6.1
• 危险类别码：
  R20/21/22,R36/37/38
• 危险品运输编号：
  UN3439
• 海关编码：
  2933990090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  保存方法：密封、阴凉、通风和干燥处。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: tert-Butyl 3-cyano-4-oxopyrrolidine-1-carboxylate
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

---

Section 3. Composition/information on ingredients.
Ingredient name: tert-Butyl 3-cyano-4-oxopyrrolidine-1-carboxylate
CAS number: 175463-32-8

---

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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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.
Storage: Store in closed vessels.

---

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
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H14N2O3
Molecular weight: 210.2

---

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.

---

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

制备方法与用途

用途

1-Boc-3-氰基-4-吡咯烷酮主要用于合成新型萘啶类抗菌剂，同时也可用于合成含有苄基肟部分的吉美沙星衍生物。

反应信息

• 作为反应物：
  描述：

  1-Boc-3-氰基-4-吡咯烷酮 在 肼 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以80%的产率得到3-氨基-5-叔丁氧羰基-吡咯并[3,4-C]吡唑
  参考文献：
  名称：

  新型5,6,5-和5,5,6-三环吡咯烷类作为有效和选择性DPP-4抑制剂的发现

  摘要：

  确定了新型有效和选择性的5,6,5-和5,5,6-三环吡咯烷二肽基肽酶IV（DPP-4）抑制剂。结构-活性关系（SAR）的工作重点是提高内在的DPP-4抑制能力，增加蛋白酶的选择性，并展示出清洁的离子通道和细胞色素P450谱，同时力图获得适合于人类每周一次给药的药代动力学谱。

  DOI：

  10.1016/j.bmcl.2016.04.020
• 作为产物：
  描述：

  N-tert-butoxycarbonyl-2-(2-cyanoethyl)aminoacetic acid ethyl ester 在 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以75%的产率得到1-Boc-3-氰基-4-吡咯烷酮
  参考文献：
  名称：

  7- (3-aminopyrrolo [3,4-c] pyrazol-5 (2H, 4H, 6H) -yl) -6-fluoro-4-oxo-1,4-dihydroquinoline-3 - 的合成和体外抗菌活性羧酸衍生物

  摘要：

  一系列新型7-(3-氨基吡咯并[3,4-c]吡唑-5(2H,4H,6H)-基)-6-氟-4-氧代-1,4-二氢喹啉-3-羧酸衍生物通过 1H-NMR、MS 和 HRMS 设计、合成和表征。评估了这些氟喹诺酮类药物对代表性革兰氏阳性和革兰氏阴性菌株的体外抗菌活性。一般而言，所有目标化合物对受试革兰氏阴性菌株均表现出较弱的效力，但大多数对包括耐甲氧西林金黄色葡萄球菌（MRSA）和包括耐甲氧西林的表皮葡萄球菌在内的金黄色葡萄球菌的生长表现出良好的抑制作用表皮葡萄球菌 (MRSE) (MIC: 0.125-8 µg/mL)。特别是，化合物 9g 比吉米沙星 (GM)、莫西沙星 (MX)、加替沙星 (GT) 和左氧氟沙星 (LV) 对金黄色葡萄球菌的效力高 2 至 32 倍。

  DOI：

  10.1002/ardp.201000160

文献信息

• [EN] 2-CYANOISOINDOLINE DERIVATIVES FOR TREATING CANCER<br/>[FR] DÉRIVÉS DE 2-CYANOISOINDOLINE POUR LE TRAITEMENT DU CANCER
  申请人：MISSION THERAPEUTICS LTD

  公开号：WO2017158388A1

  公开（公告）日：2017-09-21

  The invention relates to novel compounds of formula I which are inhibitors of deubiquitylating enzymes (DUBs) and/or desumoylating enzymes. In particular, the invention relates to the inhibition of ubiquitin C-terminal hydrolase 7 or ubiquitin specific peptidase 7 (USP7). The invention further relates to methods for the preparation of these compounds and to their use in the treatment of cancer.

  这项发明涉及公式I的新化合物，这些化合物是去泛素化酶（DUBs）和/或去泛素化酶的抑制剂。具体来说，该发明涉及抑制泛素C端水解酶7或泛素特异性肽酶7（USP7）。该发明还涉及这些化合物的制备方法以及它们在癌症治疗中的应用。
• [EN] PROCESS FOR PREPARING CHIRAL DIPEPTIDYL PEPTIDASE-IV INHIBITORS<br/>[FR] PROCÉDÉ DE PRÉPARATION D'INHIBITEURS CHIRAUX DE DIPEPTIDYL PEPTIDASE-IV
  申请人：MERCK SHARP & DOHME

  公开号：WO2016014324A1

  公开（公告）日：2016-01-28

  A process for preparing a compound of structural Formula Ia: comprising Boc deprotection with TFA of, reductive amination of:.

  制备结构式Ia化合物的过程：包括使用三氟乙酸对Boc进行去保护，还有还原胺化反应。
• 一类咪唑并芳环类化合物的制备和应用
  申请人：上海轶诺药业有限公司

  公开号：CN111039946A

  公开（公告）日：2020-04-21

  本发明提供了一类咪唑并芳环类化合物的制备和应用，具体地，本发明提供了一种如下式I所示的化合物，其中，各基团的定义如说明书中所述。所述的化合物具有TRK激酶抑制活性，可以作为治疗TRK功能异常相关疾病的药物组合物。
• Bicyclo-pyrazoles active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them
  申请人：——

  公开号：US20030171357A1

  公开（公告）日：2003-09-11

  Bicyclo-pyrazole compounds of formula (I), as herein defined, are useful for treating diseases linked to disregulated protein kinases.

  Bicyclo-pyrazole化合物的化学式（I），如本文所定义，可用于治疗与失调蛋白激酶相关的疾病。
• [EN] 6, 7 -DIHYDRO- 5H- PYRROLO [3, 4-D] PYRIMIDIN-4-YL] -QUINOLIN-3 -YLAMINE COMPOUNDS USEFUL AS FAAH MODULATORS AND USES THEREOF<br/>[FR] COMPOSÉS 6, 7 -DIHYDRO- 5H- PYRROLO [3, 4-D] PYRIMIDIN-4-YL] -QUINOLIN-3 -YLAMINE S'UTILISANT COMME MODULATEURS DE LA FAAH ET UTILISATIONS DESDITS COMPOSÉS
  申请人：RENOVIS INC

  公开号：WO2010059610A1

  公开（公告）日：2010-05-27

  Compounds are disclosed that have formula I: where A, B, L1, W, Y, R1, and R3 are as defined herein. The compounds and pharmaceutical compositions thereof are useful for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non- limiting example, pain, anxiety, depression, inflammation, cognitive disorders, weight and eating disorders, Parkinson's disease, Alzheimer's disease, spasticity, addiction, glaucoma, and others.

  揭示了具有化学式I的化合物：其中A、B、L1、W、Y、R1和R3如本文所定义。这些化合物及其药物组成物对于哺乳动物包括人类的各种疾病的预防和治疗是有用的，包括但不限于疼痛、焦虑、抑郁、炎症、认知障碍、体重和进食障碍、帕金森病、阿尔茨海默病、痉挛、成瘾、青光眼等。