金刚烷-1-甲酰肼 | 17846-15-0

• 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: 金刚烷-1-甲酰肼
• 中文别名: 金刚烷-1-羧肼
• 英文名称: adamantane-1-carbohydrazide
• 英文别名: adamantane-1-carboxylic acid hydrazide；1-adamantane carbohydrazide；damantane-1-carbohydrazide
• CAS: 17846-15-0
• 化学式: C₁₁H₁₈N₂O
• mdl: MFCD00154679
• 分子量: 194.277
• InChiKey: FJXQVRADKYKERU-UHFFFAOYSA-N

物化性质

• 熔点：
  151 °C
• 沸点：
  370.8±9.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.909
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2928000090

SDS

Name:	Adamantane-1-carbohydrazide 97% Material Safety Data Sheet
Synonym:
CAS:	17846-15-0

Section 1 - Chemical Product MSDS Name:Adamantane-1-carbohydrazide 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
17846-15-0	Adamantane-1-carbohydrazide	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. Wash mouth out with 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:
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.
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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
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# 17846-15-0: Personal Protective Equipment Eyes: Not available.
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: Solid
Color: beige
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 157 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: C11H18N2O
Molecular Weight: 194

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, acids, acid chlorides.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 17846-15-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Adamantane-1-carbohydrazide - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 17846-15-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 17846-15-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 17846-15-0 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：

  金刚烷-1-甲酰肼 在 盐酸 、 sodium nitrite 作用下， 以 水 、 甲苯 为溶剂， 反应 0.03h， 生成 1-adamantanecarbonyl azide
  参考文献：
  名称：

  [EN] FLOW CHEMISTRY SYNTHESIS OF ISOCYANATES
  [FR] SYNTHÈSE CHIMIQUE EN FLUX D'ISOCYANATES

  摘要：

  该披露提供了诸如流动化学等安全环保的方法，用于合成异氰酸酯，例如亚甲基二苯基二异氰酸酯、甲苯二异氰酸酯、己二胺二异氰酸酯、异佛尔酮二异氰酸酯和四甲基二异氰酸酯。

  公开号：

  WO2021119606A1
• 作为产物：
  描述：

  1-金刚烷甲酸 在 硫酸 、 肼 作用下， 以 乙醇 为溶剂， 反应 0.2h， 生成 金刚烷-1-甲酰肼
  参考文献：
  名称：

  Microwave Assisted Synthesis of New Adamantyltriazine Derivatives

  摘要：

  本文描述了利用传统方法和微波方法合成新的2-金刚烷基-1,2,4-三嗪衍生物，并获得了良好的产率。所提出的金刚烷基三嗪结构的表征采用MS、1H NMR和13C NMR光谱数据，并通过9c的X射线结构测定得到确认。

  DOI：

  10.2174/15701786113106660063

文献信息

• Synthesis and reactions of chroman-2-ols and their benzo analogs with N-nucleophiles
  作者：Irina А. Semenova、Kirill S. Korzhenko、Dmitry V. Osipov、Vitaly А. Osyanin、Yuri N. Klimochkin

  DOI：10.1007/s10593-020-02661-0

  日期：2020.3

  By the action of acetic acid on 2-morpholinochromanes, a series of chroman-2-ols were obtained in which the hydroxyl group is easily substituted by a primary or secondary amine or benzyl carbamate fragments. In the case of hydrazines and hydrazides of carboxylic acids, the corresponding hydrazones are isolated.

  通过乙酸对2-吗啉代苯并二氢吡喃的作用，获得了一系列的苯并二氢吡喃-2-醇，其中羟基容易被伯胺或仲胺或氨基甲酸苄酯片段取代。在肼和羧酸的酰肼的情况下，分离出相应的。
• In-silico identification of the binding mode of synthesized adamantyl derivatives inside cholinesterase enzymes
  作者：Amal Al-Aboudi、Raed A Al-Qawasmeh、Alaa Shahwan、Uzma Mahmood、Asaad Khalid、Zaheer Ul-Haq

  DOI：10.1038/aps.2014.173

  日期：2015.7

  To investigate the binding mode of synthesized adamantly derivatives inside of cholinesterase enzymes using molecular docking simulations. A series of hybrid compounds containing adamantane and hydrazide moieties was designed and synthesized. Their inhibitory activities against acetylcholinesterase (AChE) and (butyrylcholinesterase) BChE were assessed in vitro. The binding mode of the compounds inside cholinesterase enzymes was investigated using Surflex-Dock package of Sybyl7.3 software. A total of 26 adamantyl derivatives were synthesized. Among them, adamantane-1-carboxylic acid hydrazide had an almost equal inhibitory activity towards both enzymes, whereas 10 other compounds exhibited moderate inhibitory activity against BChE. The molecular docking studies demonstrated that hydrophobic interactions between the compounds and their surrounding residues in the active site played predominant roles, while hydrophilic interactions were also found. When the compounds were docked inside each enzyme, they exhibited stronger interactions with BChE over AChE, possibly due to the larger active site of BChE. The binding affinities of the compounds for BChE and AChE estimated were in agreement with the experimental data. The new adamantly derivatives selectively inhibit BChE with respect to AChE, thus making them good candidates for testing the hypothesis that BChE inhibitors would be more efficient and better tolerated than AChE inhibitors in the treatment of Alzheimer's disease.

  通过分子对接模拟研究合成的金刚烷衍生物在胆碱酯酶中的结合模式。设计并合成了一系列含有金刚烷和酰肼基团的杂化化合物，并在体外评估了它们对乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）的抑制活性。利用Sybyl7.3软件中的Surflex-Dock包研究了这些化合物在胆碱酯酶中的结合模式。总共合成了26种金刚烷衍生物。其中，金刚烷-1-羧酸酰肼对两种酶的抑制活性几乎相等，而另外10种化合物对BChE表现出中等的抑制活性。分子对接研究表明，化合物与活性位点周围残基之间的疏水相互作用起主导作用，同时也发现了亲水相互作用。当这些化合物对接在每种酶内部时，它们与BChE的相互作用更强于AChE，这可能是因为BChE的活性位点较大。对化合物对BChE和AChE的结合亲和力的估算与实验数据一致。新型的金刚烷衍生物对BChE相对于AChE具有选择性抑制作用，因此它们是检验以下假设的良好候选物：与AChE抑制剂相比，BChE抑制剂在治疗阿尔茨海默病方面更为有效且更易耐受。
• Synthesis of Dihydrothienopyridine Derivatives Fused with Triazole Rings
  作者：Péter Ábrányi-Balogh、Mátyás Milen、András Dancsó、Dávid Frigyes、László Pongó、György Keglevich

  DOI：10.1002/hc.21087

  日期：2013.5

  New dihydro[3,2-c][1,2,4]triazolo[4,3-a]pyridines were synthesized by the reaction of 4-(methylsulfanyl)-6,7-dihydrothieno[3,2-c]pyridine with acid hydrazides. One bis(dihydrothienotriazolo-pyridine) was also prepared. In a few cases, the corresponding intermediate could be detected by LC-MS. The bromophenyl derivative was involved in Suzuki and Sonogashira cross-coupling reactions. © 2013 Wiley Periodicals

  4-(甲基硫烷基)-6,7-二氢噻吩并[3,2-c]吡啶反应合成了新型二氢[3,2-c][1,2,4]三唑并[4,3-a]吡啶与酸酰肼。还制备了一种双(二氢噻吩并三唑并吡啶)。在少数情况下，可以通过 LC-MS 检测到相应的中间体。溴苯基衍生物参与 Suzuki 和 Sonogashira 交叉偶联反应。© 2013 Wiley Periodicals, Inc. 杂原子化学 24:226–233, 2013; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.21087
• Facile Synthesis of Hydrazine Derivatives of 5H-Pyrrolo[3,4-b]pyrazine and 1H-Pyrrolo[3,4-b]quinoxaline
  作者：Olga Hordiyenko、Igor Rudenko、Irina Zamkova、Oleksandr Denisenko、Angelina Biitseva、Axelle Arrault、Andrei Tolmachev

  DOI：10.1055/s-0033-1340042

  日期：——

  convenient and efficient route for the chemoselective synthesis of carbohydrazide, arenesulfonylhydrazide, and thiosemicarbazone derivatives of 5H-pyrrolo[3,4-b]pyrazine and 1H-pyrrolo[3,4-b]quinoxaline from the corresponding dinitriles and substituted hydrazines was elaborated. The synthesis of starting pyrazine-2,3-dicarbonitrile was sufficiently improved by using concentrated HCl as a catalyst. A convenient

  摘要 从相应的二腈和取代的肼类化合物化学选择性合成5 H-吡咯并[3,4- b ]吡嗪和1 H-吡咯并[3,4- b ]喹喔啉的碳酰肼，芳烃磺酰肼和硫代半脲衍生物的便捷有效途径被详细阐述。通过使用浓HCl作为催化剂，起始吡嗪-2，3-二腈的合成得到了充分改善。 从相应的二腈和取代的肼类化合物化学选择性合成5 H-吡咯并[3,4- b ]吡嗪和1 H-吡咯并[3,4- b ]喹喔啉的碳酰肼，芳烃磺酰肼和硫代半脲衍生物的便捷有效途径被详细阐述。通过使用浓HCl作为催化剂，起始吡嗪-2，3-二腈的合成得到了充分改善。
• Synthesis, characterization, cytotoxicity and antiangiogenic activity of copper(II) complexes with 1-adamantoyl hydrazone bearing pyridine rings
  作者：Marko V. Rodić、Vukadin M. Leovac、Ljiljana S. Jovanović、Vojislav Spasojević、Milan D. Joksović、Tatjana Stanojković、Ivana Z. Matić、Ljiljana S. Vojinović-Ješić、Violeta Marković

  DOI：10.1016/j.ejmech.2016.03.003

  日期：2016.6

  Investigation of anticancer potential of Cu(II) complexes, mode of cell death, apoptosis, and inhibition of angiogenesis were performed. All tested malignant cell lines (HeLa, LS174, A549, K562, and MDA-MB-231) showed high sensitivity to the examined Cu(II) complexes. It has been shown that the complexes induce apoptosis in the caspase 3-dependent manner, whereas the anti-angiogenic effects of 1, 2, and 3 have

  具有式[Cu II 2 Cu I 2（Addpy）2 Br 2（μ- Br 4）]的三齿N 2 O配体二（2-吡啶基）酮1-金刚烷基1-（Addpy）的三种新型铜配合物（1） ，catena -poly [CuCl（μ- Addpy）（μ- Cl）CuCl 2 ] n（2）和[Cu（Addpy）（NCS）2 ]（3）合成。复合物的特征在于X射线晶体学，光谱（UV-Vis，FTIR），电化学（CV）分析和磁化学测量。研究了铜（II）配合物的抗癌潜力，细胞死亡模式，细胞凋亡和血管生成的抑制作用。所有测试的恶性细胞系（HeLa，LS174，A549，K562和MDA-MB-231）均对所检查的Cu（II）复合物具有高敏感性。已经显示的是，复合物诱导细胞凋亡的胱天蛋白酶3依赖的方式，而的抗血管生成作用1，2，和3已经在将EA.hy926细胞中使用的管形成试验得到证实。