葫芦脲 水合物 | 80262-44-8

• 物质功能分类: 催化剂及助剂 - 聚合物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 中文名称: 葫芦脲 水合物
• 中文别名: 瓜环葫芦脲CB[6]；瓜环葫芦脲；葫芦[6]脲十二水合物；葫芦脲[6]；葫芦脲；葫芦脲水合物；瓜环葫芦脲 CB[6]
• 英文名称: cucurbituril
• 英文别名: cucurbit[6]uril；CB[6]；3,5,8,10,13,15,18,20,23,25,28,30,31,33,35,37,41,43,45,47,49,51,53,55-tetracosazanonadecacyclo[25.3.3.36,7.311,12.316,17.321,22.22,31.226,33.13,30.15,8.110,13.115,18.120,23.125,28.135,41.137,55.143,45.147,49.151,53]hexacontane-34,36,38,39,40,42,44,46,48,50,52,54-dodecone
• CAS: 80262-44-8
• 化学式: C₃₆H₃₆N₂₄O₁₂
• 分子量: 996.835
• InChiKey: MSBXTPRURXJCPF-UHFFFAOYSA-N

物化性质

• 熔点：
  ~470 °C
• 密度：
  2.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.8
• 重原子数：
  72
• 可旋转键数：
  0
• 环数：
  18.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  283
• 氢给体数：
  0
• 氢受体数：
  12

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

---

Section 1: Product Identification
Chemical Name: Cucurbit[6]uril (CB[6]) hydrate, 99+%
CAS Registry Number: 80262-44-8
Formula: C36H36N24O12.xH2O
EINECS Number: none
Chemical Family: macrocyclic compounds
Synonym: CB[6]

---

Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 80262-44-8 100% no data no data

---

Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract.
Primary Routes of Exposure: Ingestion, inhalation, eyes
Eye Contact: Causes slight to mild irritation of the eyes.
Skin Contact: Causes slight to mild irritation of the skin.
Inhalation: Irritating to the nose, mucous membranes and respiratory tract.
Ingestion: No information available on the physiological effects of ingestion. May be harmful if swallowed.
Acute Health Affects: Irritating to skin, eyes and respiratory tract.
Chronic Health Affects: No information on long-term chronic effects.
NTP: No
IARC: No
OSHA: No

---

SECTION 4: First Aid Measures
Immediately flush the eyes with copious amounts of water for at least 10-15 minutes. A victim may need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area with water. Remove contaminated clothes if necessary. Seek medical assistance if
Skin Exposure:
irritation persists.
Remove the victim to fresh air. Closely monitor the victim for signs of respiratory problems, such as difficulty
Inhalation:
in breathing, coughing, wheezing, or pain. In such cases seek immediate medical assistance.
Seek medical attention immediately. Keep the victim calm. Give the victim water (only if conscious). Induce
Ingestion:
vomiting only if directed by medical personnel.

---

SECTION 5: Fire Fighting Measures
Flash Point: none
Autoignition Temperature: none
Explosion Limits: none
Extinguishing Medium: carbon dioxide, dry powder or foam
If this product is involved in a fire, fire fighters should be equipped with a NIOSH approved positive pressure
Special Fire Fighting Procedures:
self-contained breathing apparatus and full protective clothing.
Hazardous Combustion and If involved in a fire this material may emit irritating fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards.

---

SECTION 6: Accidental Release Measures
Spill and Leak Procedures: Small spills can be mixed with vermiculite or sodium carbonate and swept up.

---

SECTION 7: Handling and Storage
Handling and Storage: Store in a tightly sealed container. Keep in a cool, dry, well-ventilated area.

---

SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Always wear approved safety glasses when handling a chemical substance in the laboratory.
Skin Protection: Wear protective clothing and gloves.
Ventilation: Handle the material in an efficient fume hood.
If ventilation is not available a respirator should be worn. The use of respirators requires a Respirator
Respirator:
Protection Program to be in compliance with 29 CFR 1910.134.
Ventilation: Handle the material in an efficient fume hood.
Additional Protection: No additional protection required.

---

SECTION 9: Physical and Chemical Properties
Color and Form: white powder
Molecular Weight: 996.82
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: none
Solubility in Water: insoluble

---

SECTION 10: Stability and Reactivity
Stability: air and moisture stable
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: none
Incompatibility: strong oxidizing agents
Decomposition Products: carbon monoxide, carbon dioxide, nitrogen oxides, and organic fumes

---

SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files.
Carcinogenic Effects: no data
Mutagenic Effects: no data
Tetratogenic Effects: no data

---

SECTION 12: Ecological Information
Ecological Information: No information available

---

SECTION 13: Disposal Considerations
Disposal: Dispose of according to local, state and federal regulations.

---

SECTION 14: Transportation
Shipping Name (CFR): Non-hazardous
Hazard Class (CFR): NA
Additional Hazard Class (CFR): NA
Packaging Group (CFR): NA
UN ID Number (CFR): NA
Shipping Name (IATA): Non-hazardous
Hazard Class (IATA): NA
Additional Hazard Class (IATA): NA
Packaging Group (IATA): NA
UN ID Number (IATA): NA

---

SECTION 15: Regulatory Information
TSCA: Not listed in the TSCA inventory
SARA (Title 313): Not regulated under SARA 313
Second Ingredient: none

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

葫芦脲（CB[n\）是一类在分子识别方面具有潜在应用价值的工具分子。近年来，通过已开发的CB[n]功能性客体分子及外部刺激响应原理的核酸超分子研究，已经在多个领域取得了实际应用。

反应信息

• 作为反应物：
  描述：

  葫芦脲 水合物 在 ammonium persulfate 、 水 作用下， 反应 6.0h， 生成
  参考文献：
  名称：

  Monofunctionalised cucurbit[6]uril synthesis using imidazolium host–guest complexation

  摘要：

  单羟基化的葫芦烷[6]尿素（CB[6]）首次通过在量身定制的双咪唑离子客体存在下对CB[6]进行控制氧化而制备，已通过1H NMR、ESI-MS和X射线晶体学进行了验证。此外，单羟基化的CB[6]也可以轻松进行进一步的化学修饰。

  DOI：

  10.1039/c2cc17433b
• 作为产物：
  描述：

  1,6-己二胺 生成 葫芦脲 水合物
  参考文献：
  名称：

  US2013/195751

  摘要：

  公开号：
• 作为试剂：
  描述：

  对三氟甲氧基苯胺 、 5-chloro-1H-pyrrole-2-carboxylic acid 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium pyrosulfite 、 葫芦脲 水合物 、 copper(I) bromide 作用下， 以 neat (no solvent) 为溶剂， 反应 1.0h， 以81%的产率得到5-chloro-N-(4-(trifluoromethoxy)phenyl)thiophene-2-sulfonamide
  参考文献：
  名称：

  芳香族磺酰胺的机械化学合成

  摘要：

  开发了一种三组分 Pd 催化的 K 2 S 2 O 5和胺与芳基溴化物或芳族羧酸的氨基磺酰化反应。开发该策略是为了利用机械能并适应伯胺和仲脂肪族和芳族胺，为各种磺胺类药物提供新的捷径。对反应范围和局限性的研究表明，它可以容忍广泛的官能团和许多结构模式。反应放大到克级。

  DOI：

  10.1039/d1cc03224k

文献信息

• A three dimensional framework induced by π···π stacking of 2,2′-(Alkylene-1,6-diyl)diisoquinolinium from Q[6]-based Pseudorotaxane
  作者：Zhi-Fang Fan、Xin Xiao、Yun-Qian Zhang、Sai-Feng Xue、Qian-Jiang Zhu、Zhu Tao、Gang Wei

  DOI：10.1007/s10847-011-9981-y

  日期：2011.12

  (K6)@(Q[6])}2+·2Br−·7(H2O). The compound 1 has a novel three-dimensional framework constructed of two different channels―one containing stacked isoquinolyl moieties from the K6@Q[6] pseudorotaxanes and the other containing the bromide anions. 1H NMR spectra analysis was performed and confirmed the pseudorotaxane interaction model in which the 2,2′-(alkylene-1,6-diyl)diisoquinolinium guest threads into the

  设计、合成并引入了 2,2'-(己烷-1,6-二基) 二异喹啉鎓 (K6) 的溴化物盐，构建了由 2,2'-(亚烷基-来自基于 Q[6] 的假轮烷的 1,ω-二基）二异喹啉鎓。该化合物的晶体结构表明，基于Q[6]-2,2'-(亚烷基-1,6-二基)二异喹啉鎓假轮烷的组装骨架具有(K6)@(Q[6] )}2+·2Br-·7(H2O)。化合物 1 具有由两个不同通道构成的新型三维框架——一个包含来自 K6@Q[6] 假轮烷的堆叠异喹啉基部分，另一个包含溴阴离子。进行了 1H NMR 光谱分析并证实了假轮烷相互作用模型，其中 2,2'-(亚烷基-1, 6-diyl)diisoquinolinium 客体穿入 Q[6] 的空腔，空腔内包含烷基链，两端异喹啉基部分从两个开口处突出。对水溶液中主客体包合物的吸收分光光度法和荧光光谱分析发现，复合物在主客体摩尔比为 1:1 时最稳定。在这个比率下，复合物的结合常数
• Catalytic Self-Threading:  A New Route for the Synthesis of Polyrotaxanes
  作者：Dönüs Tuncel、Joachim H. G. Steinke

  DOI：10.1021/ma034294v

  日期：2004.1.1

  Main chain and branched polyrotaxanes have been synthesized in which polymerization and rotaxane formation occur simultaneously, due to the presence of the catalytically active self-threading macrocycle cucurbit[6]uril. Using monomers that contain stopper groups to prevent the catalytic macrocycle from noncatalytic threading, it was possible to prepare polyrotaxanes in high yields with molecular weights

  已经合成了主链和支链聚轮烷，由于存在催化活性的自穿环大环葫芦[6] uril，聚合和轮烷同时发生。使用含有终止基团的单体来防止催化性大环化合物非催化性穿线，可以高收率制备分子量高达39000的聚轮烷。这些聚轮烷在结构上是完美的，因为每个结构重复单元上正好有两个大环环入。对聚合机理的研究表明，催化剂葫芦[6]尿素对所用单体的结构高度敏感，而设计较差的单体可能会导致完全失活。详细讨论了该机制的功能。
• An adamantane-based disubstituted binding motif with picomolar dissociation constants for cucurbit[n]urils in water and related quaternary assemblies
  作者：E. Babjaková、P. Branná、M. Kuczyńska、M. Rouchal、Z. Prucková、L. Dastychová、J. Vícha、R. Vícha

  DOI：10.1039/c6ra23524g

  日期：——

  A non-axial centerpiece based on 1,3-disubstituted adamantane was designed, and three new guests were prepared. In the structure of the heterotritopic guests, the central adamantane site was combined with two terminal butyl or 1-adamantyl sites. The new central binding motif displayed an extraordinarily high affinity towards CB8 (Ka = (5.3 ± 0.3) × 1012 M−1 in water) to allow formation of quaternary

  设计了一种基于1,3-二取代金刚烷的非轴心组件，并准备了三位新宾客。在杂三位客体的结构中，金刚烷的中心位点与两个末端的丁基或1-金刚烷基位点结合在一起。新的中央结合基序表现出对CB8的极高亲和力（K a =（5.3±0.3）×10 12 M -1在水中），以允许形成具有取决于大环化合物性质的几何形状的四级组装体。根据单独的结合强度，用CB8代替CB7导致四元组装的反向排列；IE，β-CD在中央部位被两个CB7单元封端，而CB8更喜欢在中央部位被两个β-CD单元封端。
• Selective molecular recognition of methylated lysines and arginines by cucurbit[6]uril and cucurbit[7]uril in aqueous solution
  作者：Mona A. Gamal-Eldin、Donal H. Macartney

  DOI：10.1039/c2ob27007b

  日期：——

  The trend in KCB[7] of LysMe3 > LysMe2 > LysMe > Lys follows the recognition pattern of the chromodomain HP1 and other LysMen protein readers. With CB[6], protonation of the guest carboxylate group is required for the formation of inclusion complexes with the LysMen series. The CB[7] host also displays modest selectivity between the asymmetric ((2.0 ± 0.3) × 103 dm3 mol−1) and symmetric ((6.1 ± 0.6)

  葫芦[7]脲选择性结合后生标记Ñ ε，Ñ ε，Ñ ε -trimethyllysine（LysMe 3，ķ CB [7] =（1.8±0.6）×10 6分米3摩尔-1）通过3500倍于赖氨酸（（5.3±0.7）×10 2 dm 3 mol -1）在水溶液中，使用离子-偶极相互作用和疏水作用，而不是阳离子-π相互作用，如p -SO 3 -calix的“芳香笼” [4]芳烃宿主或识别LysMe 3的色域蛋白。K的趋势LysMe 3 > LysMe 2 > LysMe> Lys的CB [7]遵循色域HP1和其他LysMe n蛋白阅读器的识别模式。对于CB [6]，形成LysMe n系列夹杂物需要客体羧酸酯基的质子化。CB [7]主机还在不对称（（2.0±0.3）×10 3 dm 3 mol -1）和对称（（6.1±0.6）×10 3 dm 3 mol -1）的二甲基精氨酸之间显示出适度的选择性结合比母体精氨酸或单甲基精氨酸更牢固。
• Selective synthesis of triangular cluster oxido-sulfidocomplexes of Mo and W: High yield preparations of [Mo3O2S2(H2O)9]4+, [W3O2S2(H2O)9]4+, [W2MoO2S2(H2O)9]4+ and their derivatization
  作者：Pavel A. Abramov、Maxim N. Sokolov、Rita Hernandez-Molina、Cristian Vicent、Alexander V. Virovets、Dmitry Y. Naumov、Pedro Gili、Javier Gonzalez-Platas、Vladimir P. Fedin

  DOI：10.1016/j.ica.2010.06.017

  日期：2010.10

  Reaction of [Mo2O2(μ-S)2(H2O)6]2+ with Mo(CO)6 or metallic Mo under hydrothermal conditions (140 °C, 4 M HCl) gives oxido-sulfido cluster aqua complex [Mo3(μ3-S)(μ-O)2(μ-S)(H2O)9]4+ (1). Similarly, [W3(μ3-S)(μ-O)2(μ-S)(H2O)9]4+ (2) is obtained from [W2O2(μ-S)2(H2O)6]2+ and W(CO)6. While reaction of [Mo2O2(μ-S)2(H2O)6]2+ with W(CO)6 mainly proceeds as simple reduction to give 1, [W2O2(μ-S)2(H2O)6]2+

  [Mo 2 O 2（μ-S）2（H 2 O）6 ] 2+与Mo（CO）6或金属Mo在水热条件下（140°C，4 M HCl）反应，得到氧化硫磺簇状水合物[沫3（μ 3 -S）（μ-O）2（μ-S）（H 2 O）9 ] 4+（1）。同样地，[W 3（μ 3 -S）（μ-O）2（μ-S）（H 2 O）9 ] 4+（2）由[W获得2 ö 2（μ-S）2（H 2 O）6 ] 2+和W（CO）6。[Mo 2 O 2（μ-S）2（H 2 O）6 ] 2+与W（CO）6的反应主要以简单还原的方式进行，得到1，[W 2 O 2（μ-S）2（ ħ 2 O）6 ] 2+以Mo（CO）6产生新的混合金属簇[W 2的Mo（μ 3 -S）（μ-O）2（μ-S）（H 2 O）9 ] 4+（3）为主要产品。从溶液1与葫芦[6]在HCl超分子加合物脲（CB [6]）[沫3 ö 2 š 2（H 2 O）6氯3 ] 2 CB