N-叔丁氧羰基吡咯烷-2-硼酸 | 149682-75-7

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 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: N-叔丁氧羰基吡咯烷-2-硼酸
• 中文别名: 1-Boc-吡咯烷-2-硼酸；N-叔丁氧羰基-吡咯烷-2-硼酸
• 英文名称: 1-N-Boc-pyrrolidin-2-ylboronic acid
• 英文别名: [1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-2-yl]boronic acid
• CAS: 149682-75-7
• 化学式: C₉H₁₈BNO₄
• 分子量: 215.057
• InChiKey: UIIUYLRUCQCTST-UHFFFAOYSA-N

物化性质

• 沸点：
  349.2±52.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（轻微、加热）、DMSO（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 1-N-Boc-pyrrolidin-2-ylboronic acid
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-Boc-pyrrolidin-2-ylboronic acid
CAS number: 149682-75-7

---

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.
Storage: Store in closed vessels, under −20◦C.

---

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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H18BNO4
Molecular weight: 215.1

---

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.

---

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：

  N-叔丁氧羰基吡咯烷-2-硼酸 在 bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridyl]phenyl]iridium(1+); 2-(2-pyridyl)pyridine; hexafluorophosphate 、 tetraaqua[4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]nickel(II) chloride 作用下， 以 2-甲基四氢呋喃 、 甲醇 为溶剂， 反应 24.5h， 生成 (±)-tert-butyl 2-(3-phenylpropanoyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  通过酰亚胺的 N-C 裂解协同可见光光氧化还原/镍催化合成脂肪族酮

  摘要：

  开发了一种用于合成脂肪酮的亲电、酰亚胺基、可见光促进的光氧化还原/镍催化交叉偶联反应。该协议通过 N-C(O) 键激活进行，由于吸电子基团使氮上的孤对电子离域，金属插入该键的激活能较低，从而使金属插入该键成为可能。交叉偶联反应操作简单且温和，在环境温度下进行，并且对多种官能团表现出耐受性。

  DOI：

  10.1021/acs.orglett.7b00989
• 作为产物：
  描述：

  硼酸三甲酯 在 仲丁基锂 、 盐酸 作用下， 以 四氢呋喃 、 环己烷 、 水 为溶剂， 反应 3.5h， 以88%的产率得到N-叔丁氧羰基吡咯烷-2-硼酸
  参考文献：
  名称：

  [EN] HETEROCYCLIC BORONIC ACID COMPOUNDS
  [FR] COMPOSÉS HETEROCYCLIQUES D'ACIDE BORONIQUE

  摘要：

  提供具有以下式I的二肽酶IV（DPP-IV）抑制化合物：其中n为1至3；X为CH2；S；O；CF2或C（CH3）2；Z为H；卤素；羟基；（C1-6）烷氧基；（C1-12）烷基；（C3-12）环烷基；苯基；或杂环芳基；其中苯基和杂环芳基可以选择性地为单取代或独立地多取代为R7；可选地，X与相邻环碳和Z一起形成融合的环丙基；并且可选地，含有X的环中的一个键为双键；以及CriRii，R1，R1，R3，R4和R5如本文所述。描述了制备这些化合物的方法，以及使用具有这些化合物的配方I中的药物组合来治疗糖尿病，特别是II型糖尿病，以及其他相关疾病的方法，这些药物组合包含这些化合物。还描述了含有这些化合物与其他抗糖尿病药物组合的药物组合。

  公开号：

  WO2005047297A1
• 作为试剂：
  描述：

  、 N-叔丁氧羰基吡咯烷-2-硼酸 在 N-叔丁氧羰基吡咯烷-2-硼酸 作用下， 以90的产率得到[(2R)-1-[(2S)-2-氨基-3-甲基丁酰基]吡咯烷-2-基]硼酸
  参考文献：
  名称：

  Org. Process Res. Dev. 2002, 6, 814-816

  摘要：

  DOI：

文献信息

• A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters
  作者：Fabio Lima、Upendra K. Sharma、Lars Grunenberg、Debasmita Saha、Sandra Johannsen、Joerg Sedelmeier、Erik V. Van der Eycken、Steven V. Ley

  DOI：10.1002/anie.201709690

  日期：2017.11.20

  either boronic acids or esters. This system enabled a wide range of alkyl boronic esters and aryl or alkyl boronic acids to react with electron-deficient olefins via radical addition to efficiently form C-C coupled products in a redox-neutral fashion. The Lewis base catalyst was shown to form a redox-active complex with either the boronic esters or the trimeric form of the boronic acids (boroxines) in

  我们在此报道了使用包含路易斯碱催化剂（例如奎宁环素-3-醇或4-二甲基氨基吡啶）和光氧化还原催化剂的双催化系统来从硼酸或酯产生碳自由基。该系统使多种烷基硼酸酯和芳基或烷基硼酸能够通过自由基加成与缺电子烯烃反应，以氧化还原中性的方式有效地形成CC偶联产物。路易斯碱催化剂显示出与溶液中的硼酸酯或硼酸（环硼氧烷）的三聚形式形成氧化还原活性络合物。
• Synthesis and biological activity of peptide proline-boronic acids as proteasome inhibitors
  作者：Liqiang Han、Yanzhao Wen、Ridong Li、Bo Xu、Zemei Ge、Xin Wang、Tieming Cheng、Jingrong Cui、Runtao Li

  DOI：10.1016/j.bmc.2017.05.049

  日期：2017.8

  and proteasome inhibition against three subunits. The results indicated that series II have much better biological activities than series I. The compound II-7 exhibited not only excellent biological activities with IC50 values of nM level in both cell and proteasome models, but also much better subunit selectivity. Thus, proline-boronic acid as warhead is reasonable in the design of proteasome inhibitors

  基于脯氨酸硼酸作为药效基团在激酶抑制剂中的应用以及我们先前的研究结果，以脯氨酸硼酸为战斗部，使用了两个系列的肽脯氨酸硼酸，二肽脯氨酸硼酸（I）和三肽设计并合成了脯氨酸硼酸（II）。首先评估所有合成的化合物对MGC803细胞的生物学活性，然后选择最佳的化合物II-7来测试其在六种人类肿瘤细胞系上的抗肿瘤谱以及对三个亚基的蛋白酶体抑制作用。结果表明，系列II具有比系列I更好的生物学活性。化合物II-7在细胞和蛋白酶体模型中不仅表现出优异的生物学活性（IC 50值为nM），而且亚单位选择性也好得多。因此，脯氨酸硼酸作为战斗部在蛋白酶体抑制剂的设计中是合理的。
• Generation of Functionalized Alkyl Radicals via the Direct Photoexcitation of 2,2′-(Pyridine-2,6-diyl)diphenol-Based Borates
  作者：Yusuke Miyamoto、Yuto Sumida、Hirohisa Ohmiya

  DOI：10.1021/acs.orglett.1c01996

  日期：2021.8.6

  was developed for the purpose of generating radicals via direct photoexcitation. These borates were prepared using 2,2′-(pyridine-2,6-diyl)diphenol as a tridentate ligand together with organoboronic acids or potassium trifluoroborates. The ready availability of organoboron compounds is a significant advantage of this direct photoexcitation protocol. The excited states of these borates can also serve

  为了通过直接光激发产生自由基，开发了一种新型烷基硼酸盐。这些硼酸盐是使用 2,2'-（吡啶-2,6-二基）二苯酚作为三齿配体与有机硼酸或三氟硼酸钾一起制备的。有机硼化合物的现成可用性是这种直接光激发方案的一个显着优势。这些硼酸盐的激发态也可以作为强还原剂，实现各种转变。
• The coupling of alkylboronic acids with α-(trifluoromethyl)styrenes by Lewis base/photoredox dual catalysis
  作者：Yuefeng Chen、Niannian Ni、Dongping Cheng、Xiaoliang Xu

  DOI：10.1016/j.tetlet.2020.152425

  日期：2020.10

  Under Lewis base/photoredox dual catalysis, the defluorinative alkylation of alkylboronic acids with α-(trifluoromethyl)styrenes has been reported. In this system, both primary and secondary alkyl radicals produced by alkylboronic acids can react with α-(trifluoromethyl)styrenes to generate alkylated gem-difluoroalkenes. In general, the method has mild conditions, a wide substrate scope, and good functional

  在路易斯碱/光氧化还原双重催化下，已经报道了烷基硼酸与α-（三氟甲基）苯乙烯的脱氟烷基化。在该系统中，烷基硼酸产生的伯烷基和仲烷基均可与α-（三氟甲基）苯乙烯反应生成烷基化的宝石-二氟烯烃。通常，该方法条件温和，底物范围宽，官能团耐受性好，为合成宝石-二氟烯烃提供了一条新途径。
• 脯氨酸硼酸类化合物及其制备方法和用途
  申请人：北京大学

  公开号：CN108929340B

  公开（公告）日：2019-12-13

  本发明提供了具有下述式(I)所示结构的化合物或其盐。该化合物是脯氨酸硼酸类蛋白酶体抑制剂化合物，具有良好的蛋白酶体抑制活性和优异的成药性。