苄基2-氰基-1-吡咯烷羧酸酯 | 119020-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苄基2-氰基-1-吡咯烷羧酸酯
• 中文别名: 1-CBZ-2-氰基吡咯烷
• 英文名称: benzyl 2-cyanopyrrolidine-1-carboxylate
• CAS: 119020-06-3
• 化学式: C₁₃H₁₄N₂O₂
• mdl: MFCD04115334
• 分子量: 230.266
• InChiKey: AUVGQGIWVNDVSL-UHFFFAOYSA-N

物化性质

• 沸点：
  403.6±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  | 室温 干燥 |

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 1-N-Cbz-2-cyanopyrrolidine
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 1-N-Cbz-2-cyanopyrrolidine
CAS number: 119020-06-3

---

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.

---

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.
Store in closed vessels.
Storage:

---

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
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C13H14N2O2
Molecular weight: 230.3

---

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

反应信息

• 作为反应物：
  描述：

  苄基2-氰基-1-吡咯烷羧酸酯 在 氨 、 sodium 、 1,2-二溴乙烷 、 锌 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 13.75h， 生成 hexahydro-3-oxo-3H-pyrrolo[1,2-c]imidazol-1-acetic acid methyl ester
  参考文献：
  名称：

  通过锌介导的α-氨基酸同系物立体选择性进入功能化的1,2-二胺。

  摘要：

  已经开发了由α-氨基酸进行的一般的立体选择性合成4,5-二取代的咪唑烷-2-酮的方法：关键步骤是溴乙酸在α-氨基腈上的布莱斯反应，并进一步还原。尽管用氰基硼氢化钠还原得到具有中等到良好的立体选择性的顺式和反式异构体6a-e的混合物，但是用液氨中的钠还原得到具有完全立体选择性的反式异构体8a-e。尿素的酸性水解得到4-氨基-吡咯烷酮，其可以是β，γ-二氨基酸或3-氨基吡咯烷的前体。

  DOI：

  10.1021/ol0708020
• 作为产物：
  描述：

  2-氨甲酰吡咯烷-1-羧酸苄酯 以 吡啶 、 二氯甲烷 为溶剂， 反应 2.67h， 以82%的产率得到苄基2-氰基-1-吡咯烷羧酸酯
  参考文献：
  名称：

  Inducible nitric oxide synthase dimerization inhibitors

  摘要：

  本发明涉及化合物和方法，用作一氧化氮合酶的抑制剂。本发明的某些化合物具有以下结构式： 其中T、X和Y分别选自CR 4 、N、NR 4 、S和O组成的群；U选自CR 10 和N组成的群；V选自CR 4 和N组成的群；W和W′分别选自CH 2 、CR 7 R 8 、NR 9 、O、N(O)、S(O) q 和C(O)组成的群；n、m和p分别是从0到5的整数；q为0、1或2；其他取代基如本文所定义。本发明的其他化合物具有如本文所定义的结构式。本文还公开了包含本发明化合物的药物组合物。

  公开号：

  US20060116515A1

文献信息

• Decarboxylative Cyanation of Aliphatic Carboxylic Acids via Visible-Light Flavin Photocatalysis
  作者：Nieves P. Ramirez、Burkhard König、Jose C. Gonzalez-Gomez

  DOI：10.1021/acs.orglett.9b00064

  日期：2019.3.1

  An operationally simple method is disclosed for the decarboxylative cyanation of aliphatic carboxylic acids at room temperature. Riboflavin tetraacetate, which is an inexpensive organic photocatalyst, promotes the oxidation of carboxylic acids upon visible-light activation. After decarboxylation, the generated radicals are trapped by TsCN, yielding the desired nitriles without any further additive

  公开了在室温下用于脂族羧酸的脱羧氰化的操作简单的方法。核黄素四乙酸酯是一种廉价的有机光催化剂，可在可见光激活时促进羧酸的氧化。脱羧后，在氧化还原中性过程中，生成的自由基被TsCN捕获，得到所需的腈，而无需任何其他添加剂。重要的是，该协议可以适应流量条件。
• Decarboxylative Alkynylation and Cyanation of Carboxylic Acids using Photoredox Catalysis and Hypervalent Iodine Reagents
  作者：Franck Le Vaillant、Jérôme Waser

  DOI：10.2533/chimia.2017.226

  日期：——

  in material and medicinal sciences. A convenient and straightforward access to both classes of compounds under mild conditions is, therefore, highly desirable. Herein, we disclose the decarboxylative alkynylation and cyanation of broadly available carboxylic acids using photoredox catalysis and hypervalent iodine reagents. Choices of both catalysts and reagents were crucial. Computational and experimental

  炔烃和腈是重要的官能团，可作为有机合成中的通用构建基块，并在材料和药物科学中得到应用。因此，非常需要在温和条件下方便且直接地获得两类化合物。在此，我们公开了使用光氧化还原催化和高价碘试剂对广泛可用的羧酸进行脱羧炔基化和氰化反应。催化剂和试剂的选择至关重要。计算和实验研究揭示了由试剂的氧化电位决定的两种不同的可能机理：自由基用于炔基化，离子用于氰化。
• Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation
  作者：Franck Le Vaillant、Matthew D. Wodrich、Jérôme Waser

  DOI：10.1039/c6sc04907a

  日期：——

  The one-step conversion of aliphatic carboxylic acids to the corresponding nitriles has been accomplished via the merger of visible light mediated photoredox and cyanobenziodoxolones (CBX) reagents. The reaction proceeded in high yields with natural and non-natural α-amino and α-oxy acids, affording a broad scope of nitriles with excellent tolerance of the substituents in the α position. The direct

  通过合并可见光介导的光氧化还原和氰基苯并酮（CBX）试剂，实现了脂肪族羧酸一步转化为相应的腈。天然和非天然 α-氨基酸和 α-含氧酸的反应以高产率进行，提供了广泛的腈类，并且对 α 位取代基具有优异的耐受性。还实现了二肽和药物前体的直接氰化。通过计算和实验研究了脱羧氰化的机理，并与之前开发的炔基化反应进行了比较。发现炔基化有利于直接自由基加成，而 CBX 进一步氧化成碳阳离子和氰化物加成似乎更有利于氰化。与通常假设的加成消除过程相反，提出了自由基与 EBX 试剂反应的协调机制。
• [EN] TETRA-SUBSTITUTED HETEROARYL COMPOUNDS AND THEIR USE AS MDM2 AND/OR MDM4 MODULATORS<br/>[FR] COMPOSÉS HÉTÉROARYLIQUES TÉTRASUBSTITUÉS ET LEUR UTILISATION COMME MODULATEURS DE MDM2 ET/OU MDM4
  申请人：NOVARTIS AG

  公开号：WO2011023677A1

  公开（公告）日：2011-03-03

  The invention relates to tetra-substituted heteroarylic compounds of the formula (I) wherein X1, X3 and X4 are independently C or N, Y is C-H, N-H or N, wherein the total number of nitrogen atoms represented by X1, X3, X4 and Y is 1 or 2; rings A and B are independently selected from phenyl or pyridyl; R1, R4, R', R", n and m are as defined herein. Such compounds are suitable for the treatment of a disorder or disease which is mediated by the activity of MDM2 and/or MDM4, or variants thereof.

  该发明涉及公式（I）的四取代杂芳基化合物，其中X1、X3和X4独立地为C或N，Y为C-H、N-H或N，其中由X1、X3、X4和Y表示的氮原子的总数为1或2；环A和环B独立地选自苯基或吡啶基；R1、R4、R'、R"、n和m如本文所定义。这些化合物适用于治疗由MDM2和/或MDM4的活性或其变体介导的疾病或疾病。
• C(sp³ )−H Cyanation Promoted by Visible-Light Photoredox/Phosphate Hybrid Catalysis
  作者：Takayuki Wakaki、Kentaro Sakai、Takafumi Enomoto、Mio Kondo、Shigeyuki Masaoka、Kounosuke Oisaki、Motomu Kanai

  DOI：10.1002/chem.201801746

  日期：2018.6.7

  reaction mechanism of photo‐induced DNA cleavage in nature, a C(sp3)−H cyanation reaction promoted by visible‐light photoredox/phosphate hybrid catalysis was developed. Phosphate radicals, generated by one‐electron photooxidation of phosphate salt, functioned as a hydrogen‐atom‐transfer catalyst to produce nucleophilic carbon radicals from C(sp3)−H bonds with a high bond‐dissociation energy. The resulting

  受自然界中光诱导的DNA裂解反应机制的启发，开发了由可见光光氧化还原/磷酸盐混合催化促进的C（sp 3）-H氰化反应。磷酸根盐的单电子光氧化产生的磷酸根基团起着氢原子转移催化剂的作用，从具有高键解离能的C（sp 3）-H键产生亲核碳根基。产生的碳自由基被氰基自由基源（TsCN）捕获，生成CH氰化产物。由于氰基的高功能基团耐受性和多功能性，该反应对于实现简化的构建基合成和药物样分子的后期功能化非常有用。