3-溴-1-氮杂环丁烷甲酸苄酯 | 939759-25-8

• 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: 3-溴-1-氮杂环丁烷甲酸苄酯
• 中文别名: 3-溴-1-氮杂啶羧酸苯基甲酯
• 英文名称: benzyl 3-bromoazetidine-1-carboxylate
• CAS: 939759-25-8
• 化学式: C₁₁H₁₂BrNO₂
• 分子量: 270.126
• InChiKey: SUBBMOROFINEHA-UHFFFAOYSA-N

物化性质

• 密度：
  1.546

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 3-Bromo-1-azetidinecarboxylic acid benzyl ester
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 3-Bromo-1-azetidinecarboxylic acid benzyl ester
CAS number: 939759-25-8

---

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.
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, refrigerated.
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: C11H12BrNO2
Molecular weight: 270.1

---

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 bromide.

---

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：

  3-溴-1-氮杂环丁烷甲酸苄酯 、 对甲苯磺酸甲酯 在 potassium phosphate 、 [4,4'-双(1,1-二甲基乙基)-2,2'-联吡啶]二氯化镍(II) 、 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 、 三(三甲基硅烷基)硅烷醇 、 四丁基溴化铵 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以63%的产率得到benzyl 3-methylazetidine-1-carboxylate
  参考文献：
  名称：

  金属光氧化还原催化的脂肪族溴化物的交叉电化学 Csp3-Csp3 偶联

  摘要：

  已经通过金属光氧化还原催化建立了将小烷基片段安装到药学相关脂肪族结构上的策略。在此，我们报告了三（三甲基甲硅烷基）硅烷醇可用作有效的卤素提取试剂，与光氧化还原和镍催化相结合，可实现 Csp3-Csp3 交叉亲电偶联的通用方法。在这项研究中，我们证明了各种脂肪族类药物基团可以与许多市售的小烷基亲电试剂成功偶联，包括甲苯磺酸甲酯和应变环烷基溴。此外，两个二级脂肪族碳中心的结合是有机分子构建的长期挑战，已通过多种结构形式实现。最后的，

  DOI：

  10.1021/jacs.8b12025

文献信息

• The Merger of Benzophenone HAT Photocatalysis and Silyl Radical-Induced XAT Enables Both Nickel-Catalyzed Cross-Electrophile Coupling and 1,2-Dicarbofunctionalization of Olefins
  作者：Alberto Luridiana、Daniele Mazzarella、Luca Capaldo、Juan A. Rincón、Pablo García-Losada、Carlos Mateos、Michael O. Frederick、Manuel Nuño、Wybren Jan Buma、Timothy Noël

  DOI：10.1021/acscatal.2c03805

  日期：2022.9.16

  A strategy for both cross-electrophile coupling and 1,2-dicarbofunctionalization of olefins has been developed. Carbon-centered radicals are generated from alkyl bromides by merging benzophenone hydrogen atom transfer (HAT) photocatalysis and silyl radical-induced halogen atom transfer (XAT) and are subsequently intercepted by a nickel catalyst to forge the targeted C(sp3)–C(sp2) and C(sp3)–C(sp3)

  已经开发了一种用于烯烃的交叉亲电偶联和 1,2-二碳官能化的策略。通过合并二苯甲酮氢原子转移 (HAT) 光催化和甲硅烷基自由基诱导的卤素原子转移 (XAT) 从溴代烷生成碳中心自由基，随后被镍催化剂拦截以形成目标 C(sp 3 )–C( sp 2 ) 和 C(sp 3 )–C(sp 3) 债券。温和的协议使用流动技术快速且可扩展，显示出广泛的官能团耐受性，并且适用于各种药物相关部分。机理研究表明，在光激发下，酮催化剂负责直接活化提供目标烷基自由基的硅基 XAT 试剂（HAT 介导的 XAT），并最终参与镍催化循环的转换。
• FUSED PYRIDONE COMPOUND, AND PREPARATION METHOD THEREFOR AND USE THEREOF
  申请人：SHANGHAI JEMINCARE PHARMACEUTICALS CO., LTD

  公开号：US20220389029A1

  公开（公告）日：2022-12-08

  Disclosed in the present invention are a fused pyridone compound, and a preparation method therefor and a use thereof. Specifically, the present invention discloses a compound of formula (I-B), an optical isomer thereof and a pharmaceutically acceptable salt thereof, and the use of the compound as a KRAS inhibitor.

  本发明公开了一种融合吡啶酮化合物及其制备方法和用途。具体地，本发明公开了一种I-B式化合物，其光学异构体和药学上可接受的盐，并将该化合物用作KRAS抑制剂。
• Flow photochemical Giese reaction via silane-mediated activation of alkyl bromides
  作者：Fabiola Fanini、Alberto Luridiana、Daniele Mazzarella、Antonella Ilenia Alfano、Perry van der Heide、Juan A. Rincón、Pablo García-Losada、Carlos Mateos、Michael O. Frederick、Manuel Nuño、Timothy Noël

  DOI：10.1016/j.tetlet.2023.154380

  日期：2023.3

  electron-poor olefins using alkyl bromides based on a UVA-induced silane-mediated XAT reaction. Our protocol is operationally simple, displays a broad scope and does not require a photocatalyst. Flow technology was used to reduce the reaction times and scale the process. Notably, a two-step protocol, combining the XAT protocol with a subsequent Horner-Wadsworth-Emmons reaction, has been developed to enable

  有机卤化物由于其低成本和广泛的可用性而在合成中作为基础材料发挥着关键作用。近年来，卤素原子转移 (XAT) 已成为在自由基过程中利用这些底物的可靠方法。在此，我们报告了基于 UVA 诱导的硅烷介导的 XAT 反应，使用烷基溴对缺电子烯烃进行加氢烷基化。我们的协议操作简单，显示范围广，不需要光催化剂。流动技术被用来减少反应时间和扩大过程。值得注意的是，已经开发了一个两步协议，将 XAT 协议与随后的 Horner-Wadsworth-Emmons 反应相结合，以实现 C(sp 3 ) –Br 键的烯丙基化。
• [EN] FUSED PYRIDONE COMPOUND, AND PREPARATION METHOD THEREFOR AND USE THEREOF<br/>[FR] COMPOSÉ DE PYRIDONE FUSIONNÉE, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION<br/>[ZH] 稠合吡啶酮类化合物及其制备方法和应用
  申请人：SHANGHAI JEMINCARE PHARMACEUTICALS CO LTD

  公开号：WO2021052499A1

  公开（公告）日：2021-03-25

  本发明公开了稠合吡啶酮类化合物及其制备方法和应用，具体地，本发明公开了式(I-B)所示化合物、其光学异构体及其药效上可接受的盐，以及该化合物作为KRAS抑制剂的应用。
• Reductive sp³–sp² Coupling Reactions Enable Late-Stage Modification of Pharmaceuticals
  作者：Katrina M. Mennie、Brandon A. Vara、Samuel M. Levi

  DOI：10.1021/acs.orglett.9b04320

  日期：2020.1.17

  Late-stage derivatization of pharmaceutically relevant scaffolds relies on the availability of highly functional-group tolerant reactions. Reactions that increase the sp(3) character of molecules enable the pursuit of more selective and well-tolerated pharmaceuticals. Herein, we report the use of sp(3)-sp(2) cross-electrophile reductive couplings to modify a generic ATP-competitive kinase inhibitor with a broad range of primary and secondary alkyl halide coupling partners.