2-(氧杂环丁-3-亚基)乙酸甲酯 | 1105665-34-6

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-(氧杂环丁-3-亚基)乙酸甲酯
• 中文别名: 氧杂环丁基丙烯酸甲酯
• 英文名称: methyl 2-(oxetan-3-ylidene)acetate
• CAS: 1105665-34-6
• 化学式: C₆H₈O₃
• mdl: MFCD16140399
• 分子量: 128.128
• InChiKey: QUBZUQPHJXYCSI-UHFFFAOYSA-N

物化性质

• 熔点：
  47-52°C
• 沸点：
  188.2±33.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  储存条件：2-8°C，密封保存，干燥环境中使用。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Methyl 2-(3-oxetanylidene)acetate
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 1105665-34-6
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Skin irritation (Category 2), H315
Eye irritation (Category 2), H319
Specific target organ toxicity - single exposure (Category 3), Respiratory system, H335
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xi Irritant R36/37/38
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : 2-(3-Oxetanylidene)acetic acid methyl ester
Methyl 2-(oxetan-3-ylidene)acetate
Formula : C6H8O3
Molecular Weight : 128,13 g/mol
CAS-No. : 1105665-34-6
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
Methyl 2-(3-oxetanylidene)acetate
CAS-No. 1105665-34-6 Skin Irrit. 2; Eye Irrit. 2; STOT <= 100 %
SE 3; H315, H319, H335
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
Methyl 2-(3-oxetanylidene)acetate
CAS-No. 1105665-34-6 Xi, R36/37/38 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: 2 - 8 °C
Protect from light.
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing 47 - 52 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-(氧杂环丁-3-亚基)乙酸甲酯 在 盐酸 、 lithium hydroxide monohydrate 、 adenosine triphosphate 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 magnesium chloride 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 乙腈 为溶剂， 反应 11.0h， 生成
  参考文献：
  名称：

  基于氧杂环丁烷的聚酮化合物替代物探测聚酮化合物合酶中的底物结合

  摘要：

  聚酮化合物是一大类具有广泛结构和功能的生物活性天然产物。聚酮化合物由称为聚酮化合物合酶 (PKS) 的大型多域酶复合物生物合成。研究 PKS 时的主要挑战之一是其聚β-酮底物的高反应性。这阻碍了 PKS-聚酮化合物复合物的结构和机械表征，因此，关于 PKS 如何定位不稳定的底物以进行适当的催化，同时显示出高水平的区域和立体特异性，知之甚少。作为使用氧杂环丁烷作为羰基等排体来广泛询问 PKS 化学的总体计划的第一步，我们描述了基于氧杂环丁烷的 PKS 底物模拟物的开发和应用。这使得首次对与惰性扩展单元模拟物复合的酮合酶 (KS) 的酰基酶中间体进行结构测定。晶体结构与分子动力学模拟相结合，导致了 DpsC 独特活性的拟议机制，DpsC 是柔红霉素生物合成的引发酮合酶。基于氧杂环丁烷的聚酮化合物模拟物的成功应用表明，这类新型探针可以广泛应用于对迭代 PKS 的机械酶学感兴趣的更大的生物合成社区。

  DOI：

  10.1021/jacs.7b11793
• 作为产物：
  描述：

  3-氧杂环丁酮 、 甲氧羰基亚甲基三苯基正膦 以 二氯甲烷 为溶剂， 以80 %的产率得到2-(氧杂环丁-3-亚基)乙酸甲酯
  参考文献：
  名称：

  可见光诱导光催化脱羧Giese型反应合成多种氧杂环丁烷氨基酸

  摘要：

  已经证明了利用可见光诱导的光催化脱羧吉斯型反应来不同地合成通用的 3,3'-二取代氧杂环丁烷氨基酸。 3-亚甲基氧杂环丁烷衍生的底物可轻松一步获得，并且作为自由基受体具有高反应性，从而可以高产率生产多功能氧杂环丁烷γ-和α-氨基酸。初步揭示了一种独特的环应变释放驱动的自由基加成机制。通过在含氧杂环丁烷二肽和氮杂环丁烷氨基酸的合成中的应用，以及将产物转化为新型含氧杂环丁烷螺杂环药效团，进一步凸显了制备能力。

  DOI：

  10.1002/cjoc.202300750

文献信息

• Discovery and process development of a novel TACE inhibitor for the topical treatment of psoriasis
  作者：Jean-Guy Boiteau、Gilles Ouvry、Jean-Marie Arlabosse、Stéphanie Astri、Audrey Beillard、Yushma Bhurruth-Alcor、Laetitia Bonnary、Claire Bouix-Peter、Karine Bouquet、Marilyne Bourotte、Isabelle Cardinaud、Catherine Comino、Benoît Deprez、Denis Duvert、Angélique Féret、Feriel Hacini-Rachinel、Craig S. Harris、Anne-Pascale Luzy、Arnaud Mathieu、Corinne Millois、Nicolas Orsini、Jonathan Pascau、Artur Pinto、David Piwnica、Gaëlle Polge、Arnaud Reitz、Kevin Reversé、Nicolas Rodeville、Patricia Rossio、Delphine Spiesse、Samuel Tabet、Nathalie Taquet、Loïc Tomas、Emmanuel Vial、Laurent F. Hennequin

  DOI：10.1016/j.bmc.2017.07.054

  日期：2018.2

  in-house research programs. In this article, we present the discovery of clinical candidate 26a. Starting from hits plagued with poor solubility or genotoxicity, 26a was identified through thorough multiparameter optimisation. Showing robust in vivo activity in an oxazolone-mediated inflammation model, the compound was selected for development. Following a polymorph screen, the hydrochloride salt was

  靶向TNFα途径是治疗牛皮癣的有效方法。在这一途径中，TACE成为可药物治疗的目标，并且一直是内部研究计划的重点。在本文中，我们介绍了临床候选药物26a的发现。从溶解度或基因毒性差的命中开始，通过彻底的多参数优化确定了26a。在恶唑酮介导的炎症模型中显示出强大的体内活性，因此选择了该化合物进行开发。经过多晶型物筛选后，选择盐酸盐，并有效地进行了合成，以API的总收率达到47％。
• A Direct Synthesis of Highly Substituted π‐Rich Aromatic Heterocycles from Oxetanes
  作者：Alexander R. White、Ryan A. Kozlowski、Shiou‐Chuan Tsai、Christopher D. Vanderwal

  DOI：10.1002/anie.201704119

  日期：2017.8.21

  five-membered heterocycles has driven the development of new methods for their synthesis for more than a century. Here, we disclose a general and reliable reaction manifold for the construction of highly substituted heterocycles through a facile Lewis-acid-catalyzed oxetane rearrangement. Notably, this methodology employs a keto-oxetane motif as a 1,4-dicarbonyl surrogate, which can be synthesized using

  超过一个世纪以来，普遍使用富含π的五元杂环。在这里，我们公开了一种通过可靠的路易斯酸催化的氧杂环丁烷重排构建高度取代的杂环的通用而可靠的反应流形。值得注意的是，该方法采用酮-氧杂环丁烷基序作为1,4-二羰基替代物，可以使用稳固的烷基化或烯基化反应合成，因此无需通过缩聚原料接触1,4-二羰基化合物。我们利用这种反应性来生成各种取代的呋喃和吡咯，并扩展了这种方法以生产其苯并稠合的形式。
• D3 AND 5-HT2A RECEPTOR MODULATORS
  申请人：Gobbi Luca

  公开号：US20100075983A1

  公开（公告）日：2010-03-25

  The present invention provides compounds of the general formula (I) wherein X, n and R 1 are as described herein, as well as pharmaceutically acceptable salts and esters thereof, methods for their manufacture, pharmaceutical compositions containing them and their use as medicaments. The active compounds of the present invention are dual modulators of the serotonin 5-HT 2a and dopamine D 3 receptors, useful in the treatment and/or the prevention of cognitive disorders, drug addiction, depression, anxiety, drug dependence, dementias, memory impairment, psychotic disorders comprising schizophrenia, schizoaffective disorders, bipolar disease, mania, psychotic depression, and psychoses comprising paranoia and delusions.

  本发明提供了一般式(I)的化合物，其中X、n和R1如本文所述，以及其药学上可接受的盐和酯，其制备方法，含有它们的药物组合物以及它们作为药物的用途。本发明的活性化合物是血清素5-HT2a和多巴胺D3受体的双调节剂，在认知障碍、药物成瘾、抑郁症、焦虑症、药物依赖、痴呆症、记忆障碍、包括精神分裂症、情感性精神障碍、双相情感障碍、躁狂症、精神抑郁症以及偏执狂和妄想的精神病等的治疗和/或预防中有用。
• Synthesis of oxetane/azetidine containing spirocycles
  作者：Rosalie Hamill、Benjamin Jones、Christopher M. Pask、Visuvanathar Sridharan

  DOI：10.1016/j.tetlet.2019.03.042

  日期：2019.4

  Oxetane-benzopyran spirocycles were synthesised via a palladium catalysed cyclisation-cross coupling cascade reaction whilst oxetane/azetidine-pyrrolidino isoindolone spirocycles were synthesised via a silver catalysed 1,3-dipolar cycloaddition reaction followed by a palladium catalysed carbonylation-amination process.

  氧杂环丁烷-苯并吡喃螺环是通过钯催化的环化-偶联偶合级联反应合成的，而氧杂环丁烷/氮杂环丁烷-吡咯烷基异吲哚酮螺环是通过银催化的1,3-偶极环加成反应合成的，然后是钯催化的羰基化-胺化工艺。
• [EN] HETEROCYCLIC COMPOUNDS USEFUL AS MK2 INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES UTILES COMME INHIBITEURS DE MK2
  申请人：NOVARTIS AG

  公开号：WO2009010488A1

  公开（公告）日：2009-01-22

  The present invention describes tetracyclic compounds of formula (IA) or (IB), wherein the symbols R, X, A, Y, R2, R3 and D are as defined in the specification, their use in the treatment of certain diseases, e.g. depending on MK-2 or TNF activity, and ways of manufacturing them.

  本发明描述了式（IA）或（IB）的四环化合物，其中符号R、X、A、Y、R2、R3和D如规范中所定义，它们在治疗某些疾病中的用途，例如取决于MK-2或TNF活性，并制造它们的方法。