(1S,4R)-2-偶氮双环[2,2,1]庚烷-3-酮 | 134003-03-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: (1S,4R)-2-偶氮双环[2,2,1]庚烷-3-酮
• 中文别名: (1S,4R)-2-氮杂双氮杂[2.2.1]庚烷-3-酮
• 英文名称: (±)-2-azabicyclo[2.2.1]heptan-3-one
• 英文别名: 2-azabicyclo[2.2.1]heptan-3-one；rac-(1R,4S)-2-azabicyclo[2.2.1]hept-5-en-3-one；(1S,4R)-2-Azabicyclo[2.2.1]heptan-3-one
• CAS: 134003-03-5
• 化学式: C₆H₉NO
• 分子量: 111.144
• InChiKey: UIVLZOWDXYXITH-UHNVWZDZSA-N

物化性质

• 熔点：
  76.2 °C
• 沸点：
  208.27°C (rough estimate)
• 密度：
  1.0656 (rough estimate)
• 稳定性/保质期：

  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 安全说明：
  S24/25

SDS

Name:	(1S 4R)-2-Azabicyclo[2.2.1]Heptan-3-one 95% (98% E.E.) Material Safety Data Sheet
Synonym:	None Known
CAS:	134003-03-5

Section 1 - Chemical Product MSDS Name:(1S 4R)-2-Azabicyclo[2.2.1]Heptan-3-one 95% (98% E.E.) Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
134003-03-5	(1S,4R)-2-Azabicyclo[2.2.1]Heptan-3-on	95%	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 134003-03-5: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: white to off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 76.2 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: C6H9NO
Molecular Weight: 111.14

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 134003-03-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(1S,4R)-2-Azabicyclo[2.2.1]Heptan-3-one - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Not regulated as a hazardous material.

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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# 134003-03-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 134003-03-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 134003-03-5 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：

  (1S,4R)-2-偶氮双环[2,2,1]庚烷-3-酮 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 2,4,6-三异丙基苯磺酰氯 、 四丁基氟化铵 、 水 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 47.5h， 生成 N-1-{(1S,4R)-4-(hydroxymethyl)cyclopentyl}-5'-O-{bis(phenylthio)phosphoryl}-2',3'-O-isopropylideneadenosine
  参考文献：
  名称：

  循环 ADP-核糖的稳定和细胞类型选择性类似物的合成，Ca2+-Mobilizing 第二信使。N1-核糖部分的构效关系1

  摘要：

  我们以前开发了循环 ADP-碳环核糖 (cADPcR, 2) 作为稳定模拟的循环 ADP-核糖 (cADPR, 1)，Ca(2+) 动员第二信使。一系列 N1-核糖修饰的 cADPcR 类似物，设计为 cADPR 的新型稳定模拟物，它们是 2"-脱氧类似物 3、3"-脱氧类似物 4、3"-脱氧-2"-O-(甲氧基甲基) 类似物 5、3"-O-甲基类似物 6、2",3"-dideoxy 类似物 7 和 2",3"-dideoxydidehydro 类似物 8，使用与苯硫代磷酸酯型的关键分子内缩合反应成功合成我们研究了这些类似物和 cADPR 的构象，发现腺嘌呤和 N9-核糖部分之间以及腺嘌呤和 N1-核糖部分之间的空间排斥是构象的决定因素。Ca(2+)-动员效应被系统地评估使用三个不同的生物系统，即海胆卵、 NG108-15 神经元细胞和Jurkat T 淋巴细胞。这些 cADPR 类似物对

  DOI：

  10.1021/ja050732x
• 作为产物：
  描述：

  (1S)-(+)-2-氮杂双环[2.2.1]庚-5-烯-3-酮 在 偶氮二异丁腈 、 溴 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.25h， 生成 (1S,4R)-2-偶氮双环[2,2,1]庚烷-3-酮
  参考文献：
  名称：

  Evans, Chris; McCague, Ray; Roberts, Stanley M., Journal of the Chemical Society. Perkin transactions I, 1991, # 3, p. 656 - 657

  摘要：

  DOI：
• 作为试剂：
  描述：

  3-(4-氯苯基)戊二酸酐 在 叠氮基三甲基硅烷 、 (1S,4R)-2-偶氮双环[2,2,1]庚烷-3-酮 作用下， 以 氯仿 、 乙醚 、 水 为溶剂， 反应 1.75h， 生成
  参考文献：
  名称：

  介孔戊二酸酐酸酐合成γ-氨基酸和γ-内酰胺衍生物

  摘要：

  描述了由内消旋戊二酸酐合成γ-氨基酸和γ-内酰胺衍生物的第一种方法。TMSN 3的有机催化去对称性依赖于受控生成的聚苯乙烯键合碱介导的亲核叠氮化铵物种，以促进有效的甲硅烷基叠氮化。将酰基叠氮化物中间体进行Curtius重排以得到相应的异氰酸酯后，水解/醇解可提供均匀高收率的γ-氨基酸及其N受保护的同行。结果表明，相同的中间体原位经历了前所未有的脱羧-环化级联反应，无需使用任何其他活化剂即可提供合成有用的γ-内酰胺衍生物。机械学的见解在后一个过程中调用了非常规的γ- N-羧基酸酐（γ-NCA）的中介作用。在使用这种转化方法制备的实例中，有8种具有重大医学意义的API /分子。

  DOI：

  10.1002/chem.202003280

文献信息

• Indol-amide compounds as beta-amyloid inhbitors
  申请人：F. Hoffmann-La Roche AG

  公开号：EP2722329A1

  公开（公告）日：2014-04-23

  The present invention provides compounds of formula (I) wherein Z, R1, R2, and R3 are as described herein, as well as pharmaceutically acceptable salts and esters thereof. Further the present invention is concerned with the manufacture of the compounds of formula (I), pharmaceutical compositions comprising them and their use as medicaments for the treatment of Alzheimer's disease.

  本发明提供了式(I)的化合物 其中Z、R1、R2和R3如本文所述，以及药用可接受的盐和酯。此外，本发明还涉及式(I)化合物的制备、包含它们的药物组合物以及它们用于治疗阿尔茨海默病作为药物的使用。
• INHIBITORS OF POLY(ADP-RIBOSE)POLYMERASE
  申请人：Gandhi Virajkumar B.

  公开号：US20080161280A1

  公开（公告）日：2008-07-03

  Inhibitors of poly(ADP-ribose)polymerase, ways to make them and methods of treating patients using them are disclosed.

  聚(ADP核糖)聚合酶抑制剂、制备方法以及利用它们治疗患者的方法被披露。
• CARBAZOLE-CONTAINING AMIDES, CARBAMATES, AND UREAS AS CRYPTOCHROME MODULATORS
  申请人：ReSet Therapeutics, Inc.

  公开号：US20150284362A1

  公开（公告）日：2015-10-08

  The subject matter herein is directed to carbazole-containing amide, carbamate, and urea derivatives and pharmaceutically acceptable salts or hydrates thereof of structural formula I wherein the variable R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , A, D, E, G, J, L, M, Q, a, and b are accordingly described. Also provided are pharmaceutical compositions containing the compounds of formula I to treat a Cry-mediated disease or disorder, such as diabetes, complications associated with diabetes, Cushing's syndrome, NASH, NAFLD, asthma, and COPD.

  本文涉及含有咔唑基的酰胺、碳酸酯和脲衍生物，以及其结构式I中的药用可接受盐或水合物，其中变量R1、R2、R3、R4、R5、R6、R7、A、D、E、G、J、L、M、Q、a和b分别描述。还提供了含有式I化合物的药物组合物，用于治疗Cry介导的疾病或紊乱，如糖尿病、与糖尿病相关的并发症、库欣综合征、NASH、NAFLD、哮喘和COPD。
• Enzymatic Method for the Synthesis of Blockbuster Drug Intermediates - Synthesis of Five-Membered Cyclic γ-Amino Acid and γ-Lactam Enantiomers
  作者：Enikő Forró、Ferenc Fülöp

  DOI：10.1002/ejoc.200800723

  日期：2008.11

  A very efficient enzymatic method was developed for the synthesis of cyclic γ-lactam and γ-amino acid enantiomers, intermediates for drugs with a prominent turnover (e.g., abacavir and carbovir), through the CAL-B-catalysed enantioselective (E > 200) hydrolysis of the corresponding N-Boc protected and unprotected racemic γ-lactams with H2O in iPr2O. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim

  开发了一种非常有效的酶促方法，用于通过 CAL-B 催化的对映选择性 (E > 200) 合成环状 γ-内酰胺和 γ-氨基酸对映体，它们是具有显着转化率的药物中间体（例如阿巴卡韦和卡波韦）在 iPr2O 中用 H2O 水解相应的 N-Boc 保护和未保护的外消旋 γ-内酰胺。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• NOVEL SUBSTITUTED INDANES, METHOD FOR THE PRODUCTION THEREOF, AND USE THEREOF AS DRUGS
  申请人：Schwink Lothar

  公开号：US20120022039A1

  公开（公告）日：2012-01-26

  The invention relates to substituted indanes and derivatives thereof, to physiologically acceptable salts and physiologically functional derivatives thereof, to the production thereof, to drugs containing at least one substituted indane according to the invention or derivative thereof, and to the use of the substituted indanes according to the invention and to derivatives thereof as MCH antagonists.

  该发明涉及取代吲哚烷及其衍生物，以及其生理上可接受的盐和生理功能衍生物，以及其生产，包含至少一种根据该发明的取代吲哚烷或其衍生物的药物，以及将根据该发明的取代吲哚烷及其衍生物用作MCH拮抗剂。