四氢咔唑酮 | 15128-52-6

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 四氢咔唑酮
• 中文别名: 1,2,3,4-四氢卡唑-4-酮；1,2,3,4-四氢-4-氧卡唑；1,2,3,9-四氢-4H-2-咔唑-4-酮；1,2,3,9-四氢-4H-咔唑-4-酮；1,2,3,4-四氢咔唑-4-酮
• 英文名称: 1,2,3,9-tetrahydro-4H-carbazol-4-one
• 英文别名: 2,3-dihydro-1H-carbazol-4(9H)-one；4-Oxo-1,2,3,4-tetrahydrocarbazol；1,2,3,9-tetrahydrocarbazol-4-one；1,2-dihydro-4(3H)-carbazolone；1,2-dihydrocarbazol-4(3H)-one；1,2,3,9-Tetrahydro-4H-carbazol-4-on；1,2,3,4-tetrahydro-4-oxocarbazole；1-Oxo-1,2,3,4-tetrahydro-carbazol；4-oxo-1,2,3,4-tetrahydrocarbazole
• CAS: 15128-52-6
• 化学式: C₁₂H₁₁NO
• mdl: MFCD00173749
• 分子量: 185.225
• InChiKey: DSXKDTZEIWTHRO-UHFFFAOYSA-N

物化性质

• 熔点：
  224-226°C
• 沸点：
  386.3±11.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶，加热）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 安全说明：
  S26,S36
• 海关编码：
  2933990090
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  Refrigerator

SDS

1,2,3,4-Tetrahydrocarbazol-4-one Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 1,2,3,4-Tetrahydrocarbazol-4-one

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 1,2,3,4-Tetrahydrocarbazol-4-one
Percent: >98.0%(GC)
CAS Number: 15128-52-6
Synonyms: 1,2,3,4-Tetrahydro-4-oxocarbazole
C12H11NO
Chemical Formula:

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
1,2,3,4-Tetrahydrocarbazol-4-one

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Crystal- Powder
Form:
Colour: White - Pale reddish yellow
No data available
Odour:
1,2,3,4-Tetrahydrocarbazol-4-one

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
pH: No data available
Melting point/freezing point:226°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx)
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
No data available
IARC =
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed
1,2,3,4-Tetrahydrocarbazol-4-one

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

制备方法

卡维地洛蒽丹西酮中间体的制备方法。

用途简介

暂无具体内容。

反应信息

• 作为反应物：
  描述：

  四氢咔唑酮 在 palladium on activated charcoal 1-十二烯十二碳烯α-十二碳烯α-十二碳烯 作用下， 以 三甘醇二甲醚 为溶剂， 生成 4-羟基咔唑
  参考文献：
  名称：

  β3肾上腺素能受体激动剂LY377604及其代谢物4-羟基咔唑的合成，碳14和氘标记

  摘要：

  14C-放射性标记的 4-羟基咔唑的合成是从苯胺-[U-14C] 开始的，基于氯化锌引发的苯腙-[U-14C] 和环己烷-1,3-二酮制备的苯腙的 Fischer 环化。所得四氢氧代咔唑使用碳载钯进行脱氢-芳构化。然后将芳构化的 4-羟基咔唑-[4b,5,6,7,8,8a-14C] 用于合成 14C 标记的 β3 肾上腺素能受体激动剂 LY377604。在 LY377604 的咔唑片段中引入四个氘是通过对所得四溴化物的初始溴化和随后的催化氘化实现的。类似的方法用于将 4-羟基咔唑转化为其四氘同位素。版权所有 © 2005 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.935
• 作为产物：
  描述：

  4-羟基咔唑 生成 四氢咔唑酮
  参考文献：
  名称：

  Process for the preparation of 4-hydroxycarbazole

  摘要：

  本发明提供了一种通过对1,2,3,4-四氢-4-氧基咔唑进行脱水反应制备4-羟基咔唑的方法，其中反应在水性碱性溶液中进行，使用雷尼镍作为催化剂。

  公开号：

  US04273711A1

文献信息

• Cyclodextrin-Grafted Silica-Supported Pd Nanoparticles: An Efficient and Versatile Catalyst for Ligand-Free C−C Coupling and Hydrogenation
  作者：Katia Martina、Francesca Baricco、Marina Caporaso、Gloria Berlier、Giancarlo Cravotto

  DOI：10.1002/cctc.201501225

  日期：2016.3.18

  irradiation has been shown to have a beneficial effect on catalyst preparation. The catalyst exhibited excellent activity in ligand‐free C−C Suzuki and Heck couplings with a large number of aryl iodide and bromides, in which microwave irradiation use cuts down reaction time. Pd/Si‐CD have shown high activity and selectivity in the hydrogenation reaction, and the semihydrogenation of phenyl acetylene was also

  二氧化硅是一种用途极为广泛的载体，能够容纳金属纳米颗粒（NP）并增强其稳定性和反应性。在这项研究中，我们已经为Pd NPs制备了一种新型的环糊精/二氧化硅载体，我们将其称为Pd / Si-CD。在常规条件下已经在该载体上高效且均匀地浸渍了小钯纳米颗粒，并且已经证明超声辐射对催化剂的制备具有有益的作用。该催化剂在无配体的CC Suzuki和Heck偶联以及大量的芳基碘和溴化物中表现出出色的活性，其中微波辐射的使用缩短了反应时间。Pd / Si-CD在氢化反应中显示出高活性和选择性，
• Condensed Heteroaromatic Ring Systems; XVII:¹Palladium-Catalyzed Cyclization of β-(2-Halophenyl)amino Substituted α,β-Unsaturated Ketones and Esters to 2,3-Disubstituted Indoles
  作者：Takao Sakamoto、Tatsuo Nagano、Yoshinori Kondo、Hiroshi Yamanaka

  DOI：10.1055/s-1990-26835

  日期：——

  Palladium-catalyzed cyclization of β-(2-halophenyl)amino substituted α,β-unsaturated ketones and esters, prepared from 2-haloanilines by three different methods, gave 2,3-disubstituted indoles.

  通过三种不同方法从2-卤苯胺制备的β-(2-卤苯基)氨基取代的α,β-不饱和酮和酯，在钯催化下进行环化反应，生成2,3-二取代的吲哚。
• Asymmetric Total Syntheses of Kopsane Alkaloids via a PtCl ₂ ‐Catalyzed Intramolecular [3+2] Cycloaddition
  作者：Xuelei Jia、Honghui Lei、Feipeng Han、Tao Zhang、Ying Chen、Zhengshuang Xu、Pratanphorn Nakliang、Sun Choi、Yian Guo、Tao Ye

  DOI：10.1002/anie.202005048

  日期：2020.7.27

  A concise and asymmetric total synthesis of five kopsane alkaloids that share a unique heptacyclic caged ring system was accomplished. The key transformation in the sequence involved a remarkable PtCl2‐catalyzed intramolecular [3+2] cycloaddition, which allowed for the rapid assembly of pentacyclic carbon skeletons bearing 2,3‐quaternary functionalized indoline. Expeditious construction of diverse

  一个共有一个独特的七环笼状环系统的五个古烷生物碱的简明和不对称全合成。该序列中的关键转化涉及一个显着的PtCl 2催化的分子内[3 + 2]环加成反应，该反应可快速组装带有2,3-四元功能化二氢吲哚的五环碳骨架。迅速构建具有出色的非对映选择性控制能力的各种二氢吲哚骨架，证明了这一关键转化的广泛范围和多功能性。
• Scope and Mechanistic Analysis for Chemoselective Hydrogenolysis of Carbonyl Compounds Catalyzed by a Cationic Ruthenium Hydride Complex with a Tunable Phenol Ligand
  作者：Nishantha Kalutharage、Chae S. Yi

  DOI：10.1021/jacs.5b06097

  日期：2015.9.2

  A cationic ruthenium hydride complex, [(C6H6)(PCy3)(CO)RuH](+)BF4(-) (1), with a phenol ligand was found to exhibit high catalytic activity for the hydrogenolysis of carbonyl compounds to yield the corresponding aliphatic products. The catalytic method showed exceptionally high chemoselectivity toward the carbonyl reduction over alkene hydrogenation. Kinetic and spectroscopic studies revealed a strong

  发现带有苯酚配体的阳离子氢化钌络合物 [(C6H6)(PCy3)(CO)RuH](+)BF4(-) (1) 对羰基化合物的氢解具有很高的催化活性，得到相应的脂肪族产品。该催化方法对羰基还原比烯烃氢化表现出极高的化学选择性。动力学和光谱研究揭示了苯酚配体对催化剂活性的强烈电子影响。4-甲氧基苯乙酮氢解的哈米特图显示了催化系统 1/pX-C6H4OH 的两个相反的线性斜率（对于 X = OMe、t-Bu、Et 和 Me，ρ = -3.3；对于 X = F、Cl 和 CF3)。对于由具有电子释放基团 (kH/kD = 1.7-2.5; X = OMe, Et) 的 1/pX-C6H4OH 催化的氢解反应，观察到正常的氘同位素效应，而对具有吸电子基团 (kH/kD = 0.6-0.7; X = Cl, ) 的 1/pX-C6H4OH 测量逆同位素效应。经验速率定律由 4-甲氧基苯乙酮的氢解确定：对于由
• Tandem Ullmann–Goldberg Cross-Coupling/Cyclopalladation-Reductive Elimination Reactions and Related Sequences Leading to Polyfunctionalized Benzofurans, Indoles, and Phthalanes
  作者：Faiyaz Khan、Mehvish Fatima、Moheb Shirzaei、Yen Vo、Madushani Amarasiri、Martin G. Banwell、Chenxi Ma、Jas S. Ward、Michael G. Gardiner

  DOI：10.1021/acs.orglett.9b02235

  日期：2019.8.16

  Cu[I]- and Pd[0]-based catalysts, compounds such as 1 and 7 engage in tandem Ullmann–Goldberg cross-coupling and cyclopalladation-reductive elimination reactions to give benzofurans such as 8. Related reactions involving hetero-Michael additions of o-halogenated phenols or anilines to propiolates and the Pd[0]-catalyzed cyclization of the resulting conjugates provide, in a one-pot process, alternately

  在暴露于基于Cu [I]和Pd [0]的催化剂组合时，化合物1和7会进行串联的Ullmann-Goldberg交叉偶联和环钯还原还原消除反应，得到苯并呋喃，例如8。涉及邻卤代酚或苯胺向丙酸酯的杂-迈克尔加成反应以及所得共轭物的Pd [0]催化环化的相关反应在一锅法中提供了交替官能化的苯并呋喃，吲哚或邻苯二甲酸。

表征谱图