1-[(4-硝基苯基)磺酰基]吡咯烷 | 175278-37-2

• 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: 1-[(4-硝基苯基)磺酰基]吡咯烷
• 英文名称: 1-((4-nitrophenyl)sulfonyl)pyrrolidine
• 英文别名: 1-[(4-Nitrophenyl)sulfonyl]pyrrolidine；1-(4-nitrophenyl)sulfonylpyrrolidine
• CAS: 175278-37-2
• 化学式: C₁₀H₁₂N₂O₄S
• mdl: MFCD00277216
• 分子量: 256.282
• InChiKey: FFCUNTGOHGZCQO-UHFFFAOYSA-N

物化性质

• 熔点：
  151 °C
• 沸点：
  424.8±47.0 °C(Predicted)
• 密度：
  1.432±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2935009090

SDS

Name:	1-[(4-Nitrophenyl)sulfonyl]pyrrolidine 97% Material Safety Data Sheet
Synonym:
CAS:	175278-37-2

Section 1 - Chemical Product MSDS Name:1-[(4-Nitrophenyl)sulfonyl]pyrrolidine 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
175278-37-2	1-[(4-Nitrophenyl)sulfonyl]pyrrolidine	97%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 175278-37-2: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 151 - 153 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H12N2O4S
Molecular Weight: 256

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Reducing agents, acids, bases, strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 175278-37-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-[(4-Nitrophenyl)sulfonyl]pyrrolidine - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 175278-37-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 175278-37-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 175278-37-2 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1-[(4-硝基苯基)磺酰基]吡咯烷 在 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以648 mg的产率得到4-(吡咯烷-1-磺酰基)-苯胺
  参考文献：
  名称：

  基于降冰片基的碳环核苷类似物作为细胞周期蛋白依赖性激酶 2 抑制剂的优化。

  摘要：

  我们报告了降冰片基部分作为细胞周期蛋白依赖性激酶 2 (CDK2) 抑制剂的新型结构基序的发现，该基序是通过筛选碳环核苷类似物文库确定的。通过使用药物化学方法将三个微摩尔命中扩展为一系列 16 种新化合物。它们对 CDK2 具有显着的微摩尔活性，并且该系列中最好的化合物达到了 IC 50190 纳米。通过建模和对接在分子细节中探索结合模式。使用基于量子力学的评分来合理化亲和力。总之，所发现的 9-羟甲基降冰片基部分通过联合实验-理论努力表明能够作为 CDK2 抑制剂的新取代基。这一发现为探索化学空间以寻找更有效的靶向这一类重要蛋白激酶的衍生物打开了大门。

  DOI：

  10.1002/jmr.2842
• 作为产物：
  描述：

  四氢吡咯 、 对硝基苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以98%的产率得到1-[(4-硝基苯基)磺酰基]吡咯烷
  参考文献：
  名称：

  高通量筛选和细胞外相关激酶5（ERK5）抑制剂的命中验证

  摘要：

  细胞外相关激酶5（ERK5）是癌症治疗的有希望的目标。基于IMAP FP渐进结合系统，针对ERK5开发了高通量筛选，并用于从57 617种化合物的文库中鉴定命中。筛选命中明显有四个不同的化学系列。命中的重新合成和重新测定表明，一个系列没有返回活性化合物，而三个系列返回了活性命中。结构活性研究表明，4-苯甲酰基吡咯-2-羧酰胺药效团具有很好的进一步开发潜力。鉴定了最小的激酶结合药效基团，关键实例证明了对ERK5的选择性优于p38α激酶。

  DOI：

  10.1021/acscombsci.5b00155

文献信息

• Iodine-catalyzed sulfonylation of sulfonyl hydrazides with <i>tert</i>-amines: a green and efficient protocol for the synthesis of sulfonamides
  作者：Jinyang Chen、Xiaoran Han、Lan Mei、Jinchuan Liu、Kui Du、Tuanwu Cao、Qiang Li

  DOI：10.1039/c9ra07361b

  日期：——

  This study provides a direct, sustainable and eco-friendly method for the synthesis of various sulfonamides via the sulfonylation of sulfonyl hydrazides with tert-amines. The method utilizes sulfonyl hydrazides to oxidize and couple with tertiary amines through selective cleavage of C–N bonds. In this reaction, molecular iodine was used as the catalyst and t-butyl hydroperoxide was used as the oxidant

  该研究为通过磺酰肼与叔胺磺酰化合成各种磺胺类药物提供了一种直接、可持续和环保的方法。该方法利用磺酰肼氧化并通过选择性裂解 C-N 键与叔胺偶联。在该反应中，分子碘用作催化​​剂，叔丁基过氧化氢用作氧化剂。
• TBAI-catalyzed selective synthesis of sulfonamides and β-aryl sulfonyl enamines: coupling of arenesulfonyl chlorides and sodium sulfinates with <i>tert</i>-amines
  作者：Hongmei Jiang、Xiaoyue Tang、Zhihui Xu、Huixian Wang、Kang Han、Xiaolan Yang、Yuanyuan Zhou、Yong-Lai Feng、Xian-Yong Yu、Qingwen Gui

  DOI：10.1039/c8ob02992j

  日期：——

  A simple, practical and metal-free method has been developed for the synthesis of sulfonamides and β-arylsulfonyl enamines via the selective cleavage of C–N and C–H bonds through the iodine-catalyzed oxidation of arenesulfonyl chlorides and sodium sulfinates with tert-amines. The method uses commercially available inexpensive catalysts and oxidants, and has a wide substrate scope and operational simplicity

  一种简单，实用和不含金属的方法已被开发用于磺酰胺和β-芳基磺酰基的烯胺的合成通过的C-N和C-H键的选择性裂解通过芳烃磺酰基氯化物和钠基亚磺酸盐的碘催化氧化用叔-胺类。该方法使用可商购的廉价催化剂和氧化剂，并且具有广泛的底物范围和操作简便性。
• Neuropeptide Y antagonists
  申请人：Pfizer Inc.

  公开号：US06407120B1

  公开（公告）日：2002-06-18

  The compound is a neuropeptide Y antagonist and is effective in treating feeding disorders, cardiovascular diseases and other physiological disorders.

  这种化合物是一种神经肽Y拮抗剂，对治疗进食障碍、心血管疾病和其他生理紊乱有效。
• A New Method for the Preparation of Nitrogen-containing Cyclic Compounds from<i>p</i>-Nitrobenzenesulfonamide and Alkyl Bis(diphenylphosphinite)s by Oxidation–Reduction Condensation Using 1-Azidoadamantane
  作者：Teruaki Mukaiyama、Kiichi Kuroda、Hidenori Aoki

  DOI：10.1246/cl.2005.1644

  日期：2005.12

  A new and efficient method was established for the preparation of nitrogen-containing cyclic compounds from p-nitrobenzenesulfonamide, bisphosphinites, and 1-azidoadamantane in good yields under ne...

  建立了一种以对硝基苯磺酰胺、双亚膦酸盐和1-叠氮基金刚烷为原料制备含氮环状化合物的新方法，该方法收率良好，且...
• Late-stage oxidative C(sp3)–H methylation
  作者：Kaibo Feng、Raundi E. Quevedo、Jeffrey T. Kohrt、Martins S. Oderinde、Usa Reilly、M. Christina White

  DOI：10.1038/s41586-020-2137-8

  日期：2020.4.30

  molecules1,2,3. However, existing methylation methods show limited scope and have not been demonstrated in complex settings1. Here we report a regioselective and chemoselective oxidative C(sp3)–H methylation method that is compatible with late-stage functionalization of drug scaffolds and natural products. This combines a highly site-selective and chemoselective C–H hydroxylation with a mild, functional-group-tolerant

  通常被称为“神奇的甲基效应”，甲基基团的安装——尤其是与杂原子相邻的 (α)——已被证明可以显着提高生物活性分子1,2,3的效力。然而，现有的甲基化方法显示范围有限，尚未在复杂环境中得到证实1。在这里，我们报告了一种区域选择性和化学选择性氧化 C( sp 3 )-H 甲基化方法，该方法与药物支架和天然产物的后期功能化兼容。这结合了高度位点选择性和化学选择性的 C-H 羟基化与温和的、官能团耐受的甲基化。使用小分子锰催化剂，Mn(CF 3PDP），在低负载（底物/催化剂比率为 200）下，在杂环核上提供靶向 C-H 羟基化，同时保留电子中性和富电子芳基。氟或路易斯酸辅助形成反应性亚胺或氧鎓中间体使得能够使用温和亲核的有机铝甲基化试剂，该试剂在基底上保留其他亲电子功能。我们展示了这个后期 C( sp 3)–H 甲基化在 41 个底物上，包含 16 个不同的药用重要核心，包括富电子芳基、杂环、羰