2-[(二甲基氨基)亚甲基]-1,3-环己二酮 | 85302-07-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基酰胺
• 中文名称: 2-[(二甲基氨基)亚甲基]-1,3-环己二酮
• 中文别名: 2-[(二甲基甲氨基)亚甲基]-1,3-烯己二酮
• 英文名称: 2-(dimethylaminomethylene)cyclohexane-1,3-dione
• 英文别名: 2-(dimethylamino)methylene-1,3-cyclohexanedione；2-dimethylaminomethylene-cyclohexan-1,3-dione；2-[(dimethylamino)methylidene]cyclohexane-1,3-dione；2-[(Dimethylamino)methylene]-1,3-cyclohexanedione；2-(dimethylaminomethylidene)cyclohexane-1,3-dione
• CAS: 85302-07-4
• 化学式: C₉H₁₃NO₂
• mdl: MFCD00172118
• 分子量: 167.208
• InChiKey: USUMAAZJCOVPIN-UHFFFAOYSA-N

物化性质

• 熔点：
  116 °C(Solv: chloroform (67-66-3); ligroine (8032-32-4))
• 沸点：
  274.5±40.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.555
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2922399090
• WGK Germany：
  3

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 2-Dimethylaminomethylenecyclohexane-1,3-Dione
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.
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
Acute toxicity, Oral (Category 4), H302
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
Xn Harmful R22
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)
H302 Harmful if swallowed.
Precautionary statement(s) none
Supplemental Hazard none
Statements
Other hazards
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.

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SECTION 3: Composition/information on ingredients
Substances
Molecular weight : 167,21 g/mol
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
2-Dimethylaminomethylenecyclohexane-1,3-Dione
Acute Tox. 4; H302 <= 100 %
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
2-Dimethylaminomethylenecyclohexane-1,3-Dione
Xn, R22 <= 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
Flush eyes with water as a precaution.
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
Nature of decomposition products not known.
Advice for firefighters
Wear self-contained breathing apparatus for firefighting 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. 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.
Storage class (TRGS 510): Non Combustible Solids
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
Complete suit protecting against chemicals, 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 No data available
point
f) Initial boiling point and No data available
boiling range
g) Flash point No data available
h) Evaporation 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
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
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.
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
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
No data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Acute Tox. Acute toxicity
H302 Harmful if swallowed.
Full text of R-phrases referred to under sections 2 and 3
Xn Harmful
R22 Harmful if swallowed.
Further information
Copyright 2014 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  2-[(二甲基氨基)亚甲基]-1,3-环己二酮 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-苯基-6,7-二氢-1H-吲唑-4(5H)-酮
  参考文献：
  名称：

  Nagarajan, Kuppuswamy; Arya, Vishwa Prakash; Shenoy, Sharada J., Journal of Chemical Research, Miniprint, 1986, # 5, p. 1401 - 1443

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-环己二酮 、 N,N-二甲基甲酰胺二甲基缩醛 以 neat (no solvent) 为溶剂， 反应 2.0h， 以80%的产率得到2-[(二甲基氨基)亚甲基]-1,3-环己二酮
  参考文献：
  名称：

  L-脯氨酸催化活化甲基酮或活性亚甲基化合物和 DMF-DMA 以合成 (2E)-3-Dimethylamino-2-propen-1-ones

  摘要：

  据报道，在甲基酮或活性亚甲基化合物与 DMF-DMA（N，N-二甲基甲酰胺二甲基乙缩醛）反应中发生亲核和亲电双重活化的级联有机催化。L-脯氨酸在共价和非共价同步模式下作为一种有效的有机催化剂，用于各种芳基、杂芳基和苯乙烯基甲基酮、环酮和 1,3-二酮与 DMF-DMA 的两亲性活化，以实现方便的合成多功能合成子 (2E)-1-芳基/杂芳基/苯乙烯基-3-(二甲氨基)-2-丙烯-1-酮、(E)-α-[(二甲氨基)甲叉]环烷酮和(E)-2-(在无溶剂条件下以高产率制备二甲氨基)甲亚基-1,3-二酮。

  DOI：

  10.1002/ejoc.201200778

文献信息

• [EN] TRICYCLIC COMPOUNDS AS ALLOSTERIC MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS<br/>[FR] COMPOSÉS TRICYCLIQUES COMME MODULATEURS ALLOSTÉRIQUES DES RÉCEPTEURS MÉTABOTROPES AU GLUTAMATE
  申请人：MERCK SHARP & DOHME

  公开号：WO2012006760A1

  公开（公告）日：2012-01-19

  The present invention describes and claims compounds of the Structural Formula (I), Structural Formula (II), or Structural Formula (III). In Formula (I), R1, R2, R3 and R3' are -H or methyl, or R3 and R3' taken together form a double bond, or R3' is -H and R2 and R3 taken together form a spiro-cyclopropyl substituent, R4 is -H or -F, and R5 is -H, methyl, -Cl or -Br. In Formula (II), R1 is -H, ethyl-, isopropyl-, cyclopropyl-, methyl- or methoxy-, R4 is -H or -F, and "Y" is: (a) -CH2-; (b) -CR6H-O-CR7R8-, wherein R6, R7, and R8 are independently -H or methyl; (c) -CR6H-N(R9)-CR7R8-, wherein R6, R7, and R8 are independently -H or methyl; (d) -CH2-C(R9)(R10)-C(R7)(R8)-, wherein R7, R8, R9 and R10 are independently -H or -methyl, or both R7 and R8 are -F, R9 and R10 are independently -H or -methyl, or both R9 and R10 are -F, or R9 and R10 taken together are (O=), which together with the carbon to which they are attached forms a carbonyl group.

  本发明描述和声明了结构式（I）、结构式（II）或结构式（III）的化合物。在结构式（I）中，R1、R2、R3和R3'为-H或甲基，或R3和R3'一起形成双键，或R3'为-H且R2和R3一起形成螺环丙基取代基，R4为-H或-F，R5为-H、甲基、-Cl或-Br。在结构式（II）中，R1为-H、乙基、异丙基、环丙基、甲基或甲氧基，R4为-H或-F，“Y”为：（a）-CH2-；（b）-CR6H-O-CR7R8-，其中R6、R7和R8独立地为-H或甲基；（c）-CR6H-N（R9）-CR7R8-，其中R6、R7和R8独立地为-H或甲基；（d）-CH2-C（R9）（R10）-C（R7）（R8）-，其中R7、R8、R9和R10独立地为-H或-甲基，或R7和R8都为-F，R9和R10独立地为-H或-甲基，或R9和R10都为-F，或R9和R10一起为（O=），与它们连接的碳一起形成羰基。
• [EN] BTK INHIBITORS<br/>[FR] INHIBITEURS DE BTK
  申请人：MERCK SHARP & DOHME

  公开号：WO2014116504A1

  公开（公告）日：2014-07-31

  The present invention provides Bruton's Tyrosine Kinase (Btk) inhibitor compounds according to Formula I or pharmaceutically acceptable salts thereof. Formula I or a pharmaceutically acceptable salt thereof or to pharmaceutical compositions comprising these compounds and to their use in therapy. In particular, the present invention relates to the use of Btk inhibitor compounds in the treatment of Btk mediated disorders.

  本发明提供了布鲁顿酪氨酸激酶（Btk）抑制剂化合物，该化合物符合公式I或其药用可接受的盐。公式I或其药用可接受的盐，或包含这些化合物的药物组合物及其在治疗中的用途。特别是，本发明涉及在治疗Btk介导的疾病中使用Btk抑制剂化合物。
• [EN] NEW THERAPEUTIC AGENTS FOR THE TREATMENT OF HAEMATOLOGICAL PATHOLOGIES<br/>[FR] NOUVEAUX AGENTS THÉRAPEUTIQUES POUR LE TRAITEMENT DE PATHOLOGIES HÉMATOLOGIQUES
  申请人：UNIV DEGLI STUDI DI PALERMO

  公开号：WO2021038452A1

  公开（公告）日：2021-03-04

  The present invention relates to compounds having a tetracyclic system and the use thereof as new therapeutic agents in the treatment of acute myeloid leukemia (AML), preferably in FLT3/ITD hemizygote patients resistant to conventional therapies. The invention also relates to 5,7-dihydro-4H-[1,3]thiazolo[4,5-e]isoindol-2-amine compounds useful as intermediates for the synthesis of tetracyclic imidazo[2',1':2,3][1,3]thiazolo[4,5-e]isoindole compounds.

  该发明涉及具有四环系统的化合物及其作为新的治疗剂在治疗急性髓样白血病（AML）中的用途，优选用于对传统疗法具有抗药性的FLT3/ITD半合子患者。该发明还涉及5,7-二氢-4H-[1,3]噻唑并[4,5-e]异吲哚-2-胺化合物，可用作合成四环咪唑并[2',1':2,3][1,3]噻唑并[4,5-e]异吲哚化合物的中间体。
• Synthesis of some novel pyrazolo[1,5-<i>a</i>]quinazolines and their fused derivatives
  作者：Eman Ali Ragab、Nadia Hanafy Metwally、Mona Said Mohamed

  DOI：10.1080/00397911.2016.1257722

  日期：2017.1.17

  enamines of compounds 4a,b with each of hydrazine hydrate and guanidine hydrochloride afforded pyrazolo[4″,3″:5′,6′]pyrido[4′,3′:3,4]pyrazolo[1,5-a]quinazolin-8-ones 30a,b and pyrimido[5″,4″:5′,6′]pyrido[4′,3′:3,4]pyrazolo[1,5-a]quinazolin-9(10H)-ones 33a,b, respectively. The structures of all the newly synthesized compounds were elucidated by elemental analyses and spectral data. The plausible mechanisms

  摘要 通过 5-氨基-3-氰甲基-1H-吡唑-4-甲腈 (1) 与 1,3-环己二酮衍生物的烯胺酮的环缩合反应获得了新型吡唑并[1,5-a]喹唑啉-3-甲腈 4a,b 2a,b 在回流的冰醋酸中。化合物 4a、b 与各种芳香醛缩合得到相应的亚芳基衍生物 6a-j。另一方面，4a,b 与邻羟基苯甲醛缩合生成多杂环化合物 10a-h。化合物 4a、b 与芳基重氮氯化物偶联导致形成 2-芳基腙衍生物 12a-h。此外，化合物 4a、b 与异硫氰酸苯酯反应，然后加入氯乙酸乙酯和氯乙腈，得到基于吡唑并 [1,5-a] 喹唑啉核的多杂环化合物。化合物4a的反应，b 与异硫氰酸苯酯和元素硫反应得到噻唑-2-硫酮衍生物 25a,b。化合物4a、b的烯胺与水合肼和盐酸胍各自反应得到吡唑并[4″,3″:5',6']吡啶并[4',3':3,4]吡唑并[1,5- a]quinazolin-8-ones 30a,b
• 一种具有HDAC6抑制活性的硫醇类化合物及 其应用
  申请人：沈阳药科大学

  公开号：CN109384793B

  公开（公告）日：2021-05-07

  本发明属于医药技术领域，涉及一种具有抗肿瘤活性的硫醇类化合物，具体涉及含有6(7)‑取代‑N‑(6‑巯基己基)‑吡唑并[3,4‑e]吲唑‑3‑甲酰胺片段和吡唑并喹啉/异喹啉片段的硫醇类化合物及其药学上可接受的盐、水合物，及其包含所述化合物和其药学上可接受的盐、水合物作为活性成分的药物组合物，以及它们在制备组蛋白去乙酰化酶抑制剂，用于制备治疗和/或预防癌症药物中的用途。本发明所述化合物的结构如式I所示：其中，A、X、R如权利要求和说明书所述。