7-硫唑嘌呤双环[4.2.0]辛烷-8-酮 | 34102-49-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 中文名称: 7-硫唑嘌呤双环[4.2.0]辛烷-8-酮
• 英文名称: 7-azabicyclo<4.2.0>octan-8-one
• 英文别名: (+/-)-7-azabicyclo[4.2.0]octan-8-one；7-azabicyclo[4.2.0]octan-8-one
• CAS: 34102-49-3
• 化学式: C₇H₁₁NO
• mdl: MFCD01863278
• 分子量: 125.17
• InChiKey: SQHJLZVUXVHXKC-UHFFFAOYSA-N

物化性质

• 熔点：
  48-50 °C
• 沸点：
  232.64°C (rough estimate)
• 密度：
  1.0459 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933790090

SDS

Name:	7-Azabicyclo[4.2.0]heptan-8-one 98% Material Safety Data Sheet
Synonym:	None Known
CAS:	34102-49-3

Section 1 - Chemical Product MSDS Name:7-Azabicyclo[4.2.0]heptan-8-one 98% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
34102-49-3	7-Azabicyclo[4.2.0]heptan-8-one	98%	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: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. 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 cool, dry place. Store in a tightly closed container.

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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# 34102-49-3: 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: Crystals
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 48-50 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: C7H11NO
Molecular Weight: 125.0831

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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:
Excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 34102-49-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
7-Azabicyclo[4.2.0]heptan-8-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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 34102-49-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 34102-49-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 34102-49-3 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：

  7-硫唑嘌呤双环[4.2.0]辛烷-8-酮 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 72.5h， 生成 1-(R)-cis-2-aminocyclohexanemethanol
  参考文献：
  名称：

  核苷的 1-[2-(羟甲基)环己基]嘧啶类似物的合成：比较研究

  摘要：

  报道了一系列新的嘧啶（环己烷衍生物）的 1,2-二取代碳核苷类似物的合成。对于尿苷类似物 5a 的合成，在氨基醇 3 的氨基上或在前身 β-内酰胺 1 的酰胺基上构建碱基比碱基与受保护的二醇缩合更有效。5a 的顺式构型通过 X 射线晶体学证实。化合物 5a 在尿嘧啶 5 位被 Cl、Br 和 I 卤化。

  DOI：

  10.1055/s-2004-831224
• 作为产物：
  描述：

  氯磺酰异氰酸酯 、 环己烷 生成 7-硫唑嘌呤双环[4.2.0]辛烷-8-酮
  参考文献：
  名称：

  Electron impact and ammonia chemical ionization mass spectra ofn-azabicyclo[m.2.0]alkan-(n + 1)-ones (m = 3-6,n = 6-9)

  摘要：

  AbstractElectron impact induced fragmentation of the title compounds obeys a route where the lactam moiety, OCNH, is cleaved first, with the accompanying formation of a cycloalkene ion. This can be verified by low‐resolution, high‐resolution, B/E and B2/E spectra as well as by collisional activation spectra of, for example, the ions m/z 82 and 67 from 7‐azabicyclo[4.2.0]octan‐8‐one and from cyclohexene. The only, and fairly weak, fragment ions including O and N are [C3H3O]+, [CkH2k‐2N]+ (k = 5–8) and [C3H6N]+. The ammonia chemical ionization spectra are also characteristic for all four lactams and show the same dominant ions in all cases, namely [M + 1]+, [M + 1 + NH3]+˙ and [2 M + 1]+˙.

  DOI：

  10.1002/oms.1210210202

文献信息

• 1,3-dipolar cycloadditions of 2-Ethoxy- and 2-(ethylthio)-1-azetines with nitrile oxides, nitrile ylides and nitrilimines: An unexpected 1,2,4-triazole formation.
  作者：Karl Hemming、Abdul-Bassett N. Luheshi、Alan D. Redhouse、Robert K. Smalley、J.Robin Thompson、Peter D. Kennewell、R. Westwood

  DOI：10.1016/s0040-4020(01)85755-0

  日期：1993.1

  1,3-dipolar cycloadditions with nitrile oxides and nitrile ylides to give stable 4,5-bicyclic cycloadducts. With nitrilimines, however, the expected 1,3-dipolar cycloadducts and/or unexpected ring-opened products, namely 1,2,4-triazoles, are formed depending on the nature of the nitrilimine N-substituent. In contrast, the azetines fail to react with nitrile sulphides, azomethine ylides, nitrones, aryl

  2-乙氧基和2-（乙硫基）-1-氮杂环丁烷容易与腈氧化物和腈发生1,3-偶极环加成反应，得到稳定的4,5-双环环加合物。然而，对于腈亚胺，取决于腈亚胺N-取代基的性质，形成了预期的1，3-偶极环加合物和/或未预期的开环产物，即1,2,4-三唑。相反，氮杂环丁烷不能与腈硫化物，甲亚胺基亚胺，硝酮，芳基叠氮化物和各种二烯反应。
• Photochemical Rearrangement of <i>N</i>-Chlorolactams: A Route to <i>N</i>-Heterocycles through Concerted Ring Contraction
  作者：Dana K. Winter、Alexandre Drouin、Jean Lessard、Claude Spino

  DOI：10.1021/jo100181h

  日期：2010.4.16

  We report a novel ring contraction allowing the direct conversion of N-chlorolactams to their corresponding ring-contraction N-heterocycles upon photolysis. Results show that the rearrangement occurs with a variety of N-chlorolactams and that the greater the substitution at the migrating carbon, the greater the yield of product. Importantly, stereochemistry at the migrating carbon is conserved in the

  我们报道了一种新颖的环收缩，其允许N-氯内酰胺在光解后直接转化为其相应的环收缩N-杂环。结果表明，各种N-氯内酰胺都发生了重排，并且在迁移的碳上取代量越大，产物的收率就越高。重要的是，产物中保留了迁移碳处的立体化学。分离出重排产物，其为氨基甲酸甲酯，收率从17％到58％不等，主要副产物为可回收的母体内酰胺。
• Highly Efficient Methanolysis of Bicyclic β-Lactams to β-Amino Ester Using Silica Chloride
  作者：Manisha Sathe、Ramarao Ghorpade、Mahabir Parshad Kaushik

  DOI：10.1246/cl.2006.1004

  日期：2006.9

  Silica chloride is used as an effective heterogeneous catalyst for the methanolysis of highly constrained cyclic β-lactam to afford β-amino ester under mild acidic conditions with quantitative yields.

  氯化硅作为一种有效的异相催化剂，可用于在弱酸性条件下对高度受限的环状 β-内酰胺进行甲醇分解，以获得定量的 β-氨基酯。
• 5-HT 3 RECEPTOR AGONIST, NOVEL THIAZOLE DERIVATIVE, AND INTERMEDIATE THEREFOR
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：EP0749966A1

  公开（公告）日：1996-12-27

  A 5-HT3 receptor agonist containing a thiazole derivative represented by general formula (I) as the effective ingredient; a specified compound useful as a 5-HT3 receptor agonist; and a specified thioamide derivative useful as an intermediate therefor. wherein each symbol represents the following meaning: Ring A: the following ring which may be substituted by one or more substituents selected from the group consisting of a halogen atom, a lower alkyl group and a lower alkoxyl group: 1) a benzene ring, or 2) a 5-membered or 6-membered unsaturated heterocyclic ring having one or two hetero atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, L1 and L2: one of them represents a single bond, and the other one represents non-existence, or an alkylene group having 1 to 4 carbon atoms or an alkenylene group having 2 to 5 carbon atoms, R: a group represented by one of the following formulae: L3: a lower alkylene group, L4: a single bond or a lower alkylene group, R1 and R2: the same or different and individually a hydrogen atom, a lower alkyl group or an amino-protecting group, R3: a hydrogen atom, a lower alkyl group, an oxo group or a protected or unprotected amino group, R4: non-existence or a hydrogen atom, a lower alkyl group, an aralkyl group or an amino-protecting group, Ring B: the following monocyclic or bicyclic ring which may contain an oxygen atom: 1) a nitrogen-containing saturated heterocyclic ring having 4 to 16 ring-forming atoms, or 2) a nitrogen-containing heterocyclic ring having one unsaturated bond and 4 to 16 ring-forming atoms, and Ring D: a saturated carbon ring having 4 to 8 ring-forming atoms,

  一种 5-HT3 受体激动剂，含有作为有效成分的通式(I)代表的噻唑衍生物；一种用作 5-HT3 受体激动剂的特定化合物；以及一种用作其中间体的特定硫酰胺衍生物。 其中各符号代表以下含义： 环 A：可被选自卤素原子、低级烷基和低级烷氧基的一个或多个取代基取代的下环： 1) 苯环，或 2) 5 元或 6 元不饱和杂环，其中有一个或两个杂原子，选自由氮原子、氧原子和硫原子组成的组、 L1 和 L2：其中一个代表单键，另一个代表不存在的键，或代表具有 1 至 4 个碳原子的亚烷基或具有 2 至 5 个碳原子的烯基、 R：由下式之一代表的基团： L3：低级亚烷基、 L4：单键或低级亚烷基、 R1和R2：相同或不同，各自为氢原子、低级烷基或氨基保护基团、 R3：一个氢原子、一个低级烷基、一个氧代基团或一个受保护或不受保护的氨基、 R4：不存在或为氢原子、低级烷基、芳烷基或氨基保护基团、 环 B：可含有一个氧原子的单环或双环： 1) 具有 4 至 16 个成环原子的含氮饱和杂环，或 2) 具有一个不饱和键和 4 至 16 个成环原子的含氮杂环，以及 环 D：具有 4 至 8 个成环原子的饱和碳环、
• Poly-β-peptides from functionalized β-lactam monomers and antibacterial compositions containing same
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US10323121B2

  公开（公告）日：2019-06-18

  Disclosed is a method of making β-polypeptides. The method includes polymerizing β-lactam-containing monomers in the presence of a base initiator and a co-initiator which is not a metal-containing molecule to yield the product β-polypeptides. Specifically disclosed are methods wherein the base initiator is potassium t-butoxide, lithium bis(trimethylsilyl)amide (LiN(TMS)2), potassium bis(trimethyl-silyl)amide, and sodium ethoxide, and the reaction is carried out in a solvent such as chloroform, dichloromethane, dimethylsulfoxide, or tetrahydrofuran.

  本发明公开了一种制造β-多肽的方法。该方法包括在碱引发剂和非含金属分子的助引发剂存在下，使含β-内酰胺的单体聚合，生成β-多肽。具体公开的方法是碱引发剂为叔丁醇钾、双（三甲基硅基）酰胺锂（LiN(TMS)2）、双（三甲基硅基）酰胺钾和乙醇钠，反应在氯仿、二氯甲烷、二甲亚砜或四氢呋喃等溶剂中进行。