(1S)-(+)-2-氮杂双环[2.2.1]庚-5-烯-3-酮 | 130931-83-8

• 物质功能分类: 医药中间体 - 原料药中间体
• 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: (1S)-(+)-2-氮杂双环[2.2.1]庚-5-烯-3-酮
• 中文别名: (1S,4R)-2-氮杂双环[2.2.1]庚烷-5-烯-3-酮
• 英文名称: (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one
• 英文别名: 2-azabicyclo[2.2.1]hept-5-en-3-one；Vince lactam；(1S,4R)-2-azabicyclo<2.2.1>hept-5-en-3-one；(1S)-(+)-2-azabicyclo[2.2.1]hept-5-en-3-one；(1S,4R)-2-azabicyclo[2.2.1]hept-5-en-3-one
• CAS: 130931-83-8
• 化学式: C₆H₇NO
• 分子量: 109.128
• InChiKey: DDUFYKNOXPZZIW-CRCLSJGQSA-N

物化性质

• 熔点：
  94-97 °C(lit.)
• 沸点：
  319.3±0.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2933790090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  应存于阴凉干燥环境中。

SDS

Name:	(+)-2-Azabicyclo[2.2.1]Hept-5-en-3-One 98% (HPLC) >95% e.e. Material Safety Data Sheet
Synonym:	None known
CAS:	130931-83-8

Section 1 - Chemical Product MSDS Name:(+)-2-Azabicyclo[2.2.1]Hept-5-en-3-One 98% (HPLC) >95% e.e. Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
130931-83-8	(+)-2-Azabicyclo[2.2.1]Hept-5-en-3-One	98	unlisted

Hazard Symbols: XN
Risk Phrases: 22 43

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed. May cause sensitization by skin contact.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May cause skin sensitization, an allergic reaction, which becomes evident upon re-exposure to this material.
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:
Repeated exposure may cause sensitization dermatitis.

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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.
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:

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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 agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate 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. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. 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# 130931-83-8: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: off-white to beige
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 92 - 100 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C6H7NO
Molecular Weight: 109.13

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 130931-83-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(+)-2-Azabicyclo[2.2.1]Hept-5-en-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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
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: XN
Risk Phrases:
R 22 Harmful if swallowed.
R 43 May cause sensitization by skin contact.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 130931-83-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 130931-83-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 130931-83-8 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

制备方法与用途

(1S)-(+)-2-氮杂双环[2.2.1]庚-5-烯-3-酮，又名(1S，4R)-2-氮杂双环[2.2.1]庚-5-烯-3-酮、氮杂双环或文斯内脂，是一种重要的有机合成中间体。它可用于合成阿巴卡韦和帕拉米韦等原料药。

反应信息

• 作为反应物：
  描述：

  (1S)-(+)-2-氮杂双环[2.2.1]庚-5-烯-3-酮 在 palladium 10% on activated carbon 盐酸 、 lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 2.0h， 生成 benzyl (1S,3R)-3-((diphenylmethylene)amino)cyclopentane-1-carboxylate
  参考文献：
  名称：

  Alkylamino, arylamino, and sulfonamido cyclopentyl amide modulators of chemokine receptor activity

  摘要：

  公式(I)的化合物是化学趋化因子受体活性调节剂，对预防或治疗某些炎症和免疫调节性疾病和疾病、过敏性疾病、包括过敏性鼻炎、皮炎、结膜炎和哮喘等特应性疾病，以及风湿性关节炎和动脉粥样硬化等自身免疫病理学，以及包含这些化合物的药物组合物，以及这些化合物和组合物在涉及化学趋化因子受体的疾病的预防或治疗中的用途。

  公开号：

  US20070117797A1
• 作为产物：
  描述：

  cis-1,2,3,6-tetrahydrophthalic anhydride 在 sodium tetrahydroborate 、 camphor-10-sulfonic acid 、 (4R,5R)-2,2-二甲基-a,a,a',a'-四苯基-1,3-二氧戊环-4,5-二甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 (1S)-(+)-2-氮杂双环[2.2.1]庚-5-烯-3-酮
  参考文献：
  名称：

  的非还原对映体选择性开环ñ -二异丙与α，α，α'，α'-四芳基-1,3-二氧戊环-4,5- dimethanolate（甲基磺酰基）二甲

  摘要：

  二环丙氧基钛TADDOLate将双环和三环内消旋-N-（甲基磺酰基）二甲酰亚胺1a-f对映体转化为异丙基[（磺酰胺基）羰基]-羧酸盐2a-f（产率为75-92％；参见方案3）。产物的对映体比例在86:14至97：3之间，并且从CH 2 Cl 2 /己烷中重结晶得到对映体纯的磺酰胺基酯2（方案3）。对映选择性与所用TADDOL的对映体过量显示线性关系（图3）。还原酯基和羧酰胺基（LiAlH 4）和酰亚胺开环的产物2中磺酰胺基（Red-Al）的额外还原裂解分别得到羟基磺酰胺3和氨基醇4（流程4）。磺酰胺基酯2的绝对构型是通过化学相关性（与2a，b；方案6），对3e的樟脑酸酯的X射线分析（图1）以及对羟基苯甲酸酯的19 F-NMR分析确定的羟基磺酰胺3的较硬酯（表1）。对于伯醇和胺的的绝对构型的分配的一般建议式HXCH 2 CHR 1 - [R 2，X = O，NH，建议（见11在表1中）。从2

  DOI：

  10.1002/hlca.19960790328

文献信息

• [EN] HORMONE RECEPTOR MODULATORS FOR TREATING METABOLIC MUTAGENIC AND FIBROTIC CONDITIONS AND DISORDERS<br/>[FR] MODULATEURS DU RÉCEPTEUR HORMONAL POUR LE TRAITEMENT D'ÉTATS ET DE TROUBLES MÉTABOLIQUES MUTAGÈNES ET FIBROTIQUES
  申请人：ARDELYX INC

  公开号：WO2019055808A1

  公开（公告）日：2019-03-21

  The invention relates to activators of FXR useful in the treatment of autoimmune disorders, liver disease, intestinal disease, kidney disease, cancer, and other diseases in which FXR plays a role, having the Formula (I): wherein L1, A, X1, X2, Y1, Y2, Y3, Y4, R1, R2, and R3 are described herein.

  这项发明涉及FXR的激活剂，可用于治疗自身免疫性疾病、肝病、肠道疾病、肾脏疾病、癌症以及FXR发挥作用的其他疾病，其化学式为（I）：其中L1、A、X1、X2、Y1、Y2、Y3、Y4、R1、R2和R3如本文所述。
• Benzoxazinyl-amidocyclopentyl-heterocyclic modulators of chemokine receptors
  申请人：Goble D. Stephen

  公开号：US20070238723A1

  公开（公告）日：2007-10-11

  Cyclopentyl compounds linked to a benzoxazinyl group through an amido moiety utilizing the ring nitrogen of the benzoxazine, and further substituted with a heterocyclic moiety, such compounds represented by formula I: which are used to modulate the CCR-2 chemokine receptor to prevent or treat inflammatory and immunoregulatory disorders and diseases, allergic diseases, atopic conditions including allergic rhinitis, dermatitis, conjunctivitis, and asthma, as well as autoimmune pathologies such as rheumatoid arthritis and atherosclerosis; and pharmaceutical compositions comprising these compounds and the use of these compounds and compositions.

  环戊基化合物通过酰胺基团与苯并噁唑基团相连，利用苯并噁唑环的环氮原子，并进一步用杂环基团取代，这些化合物由式I表示： 用于调节CCR-2趋化因子受体，以预防或治疗炎症和免疫调节性疾病和疾病，过敏性疾病，包括过敏性鼻炎，皮炎，结膜炎和哮喘，以及类风湿性关节炎和动脉粥样硬化等自身免疫病理病变；以及包含这些化合物的药物组合物和这些化合物和组合物的使用。
• A Mitsunobu reaction to functionalized cyclic and bicyclic N-arylamines
  作者：Daniel M. Gill、Matthew Iveson、Ian Collins、Alan M. Jones

  DOI：10.1016/j.tetlet.2017.12.017

  日期：2018.1

  The scope of an unexpected Mitsunobu cyclisation to prepare N-arylated Fsp3-enriched azacycles was investigated. In the current study, we have identified whether a pKa-dependent Mitsunobu cyclodehydration or a pKa-independent Mitsunobu intramolecular reaction was in operation. A Mitsunobu reaction, creating a leaving group, followed by intramolecular nucleophilic displacement was determined to be the

  研究了意外的Mitsunobu环化以制备富含N-芳基化的F sp 3的氮杂环的范围。在当前的研究中，我们已经确定是否正在运行p Ka依赖的Mitsunobu环脱水或p Ka依赖的Mitsunobu分子内反应。Mitsunobu反应，产生离去基团，随后帧内分子亲核置换被确定为主要的途径。
• Carbocyclic Ribosylamines:  Synthesis of 5-Substituted Carbocyclic β-Ribofuranosylamines
  作者：James T. Slama、Nimish Mehta、Ewa Skrzypczak-Jankun

  DOI：10.1021/jo060920l

  日期：2006.9.1

  exo-face of the olefin, yielding hydroxylation products that can be converted into analogues of carbocyclic ribosides. Conversely, a sterically small protecting group permits OsO4 approach from the endo-face, yielding hydroxylation products analogous to carbocyclic lyxosides. A key intermediate for carbocyclic sugar production, (1S,2S,3R, 4R,5S)-1-(tert-butyloxycarbonyl)amino-5-bromo-2,3-(dimethylmeth

  开发了5'-取代的碳环核苷类似物的5-取代的环戊胺前体的合成。我们表明，的OsO的立体化学4的顶部溴化内酰胺的催化的羟基化，7-溴-2-氮杂双环[2.2.1]庚-5-烯-3-酮，可以通过内酰胺的适当选择控制NH保护基。较大的立体基团将羟基化作用引导至烯烃的外表面，从而产生可以转化为碳环核糖苷类似物的羟基化产物。相反，空间小的保护基团允许OsO 4从内表面进入，产生类似于碳环lyxosides的羟基化产物。碳环糖生产的关键中间体（1 S，2 S，3 R，4 R，5 S）-1-（叔丁氧基羰基）氨基-5-溴-2,3-（二甲基亚甲基）二氧基-4-羟甲基环戊烷是从对映体纯的内酰胺开始合成的，（1 S）-（+）-2-氮杂双环[2.2.1]庚-5-烯-3-酮，分七个步骤，总收率为21％。
• [EN] NOVEL DIPEPTIDYL PEPTIDASE IV INHIBITORS; PROCESSES FOR THEIR PREPARATION AND COMPOSITIONS THEREOF<br/>[FR] NOUVEAUX INHIBITEURS DE DIPEPTIDYLE PEPTIDASE IV, LEUR PROCEDES DE PREPARATION ET COMPOSITIONS EN COMPORTANT
  申请人：GLENMARK PHARMACEUTICALS LTD

  公开号：WO2005075426A1

  公开（公告）日：2005-08-18

  The present invention relates to novel dipeptidyl peptidase IV (DPP-IV) inhibitors or general formula (1) useful for treating diabetes, non-insulin dependent diabetes mellitus, impaired glucose tolerance, inflammatory bowel disease, ulcerative colitis,Chron’s disease, obesity, and metabolic syndrome.

  本发明涉及一种新型二肽基肽酶IV（DPP-IV）抑制剂，其一般式（1）用于治疗糖尿病、非胰岛素依赖型糖尿病、糖耐量受损、炎症性肠病、溃疡性结肠炎、克罗恩病、肥胖症和代谢综合征。