1,2-O-亚环己基-Alpha-D-呋喃葡萄糖 | 16832-21-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,2-O-亚环己基-Alpha-D-呋喃葡萄糖
• 中文别名: 1,2-O-亚环己基-a-D-呋喃葡萄糖；1,2-O-亚环己基-α-D-呋喃葡萄糖
• 英文名称: 1,2-O-cyclohexylidene-α-D-glucofuranose
• 英文别名: 1,2,O-Cyclohexylidenglucofuranose；1,2-O-Cyclohexylidene-alpha-D-glucofuranose；(1R)-1-[(3aR,5R,6S,6aR)-6-hydroxyspiro[3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-2,1'-cyclohexane]-5-yl]ethane-1,2-diol
• CAS: 16832-21-6
• 化学式: C₁₂H₂₀O₆
• 分子量: 260.287
• InChiKey: KAUCUKASFLXURN-RCZSTQMZSA-N

物化性质

• 熔点：
  163-168 °C(lit.)
• 沸点：
  363.54°C (rough estimate)
• 密度：
  1.2377 (rough estimate)
• 稳定性/保质期：
  <p align="left" style="text-indent: -18pt; margin-left: 36pt; mso-pagination: widow-orphan">按规定使用不会分解，避氧化剂。</p>

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  29400090
• 安全说明：
  S24/25
• 储存条件：
  存放于密闭、阴凉、干燥处即可。

SDS

Name:	1 2-O-Cyclohexylidene-Alpha-D-Glucofuranose 98% Material Safety Data Sheet
Synonym:	None Known
CAS:	16832-21-6

Section 1 - Chemical Product MSDS Name:1 2-O-Cyclohexylidene-Alpha-D-Glucofuranose 98% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
16832-21-6	1,2-O-Cyclohexylidene-Alpha-D-Glucofur	98%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or 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:

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate 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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 16832-21-6: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
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: Needles
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 152.00 - 155.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H20O6
Molecular Weight: 260.28

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 16832-21-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1,2-O-Cyclohexylidene-Alpha-D-Glucofuranose - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 16832-21-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 16832-21-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 16832-21-6 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：

  1,2-O-亚环己基-Alpha-D-呋喃葡萄糖 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以66%的产率得到1,2-O-cyclohexylidene-3,5,6-tri-O-propargyl-α-D-glucofuranose
  参考文献：
  名称：

  Nascent-HBr催化去除水性表面活性剂中的正交保护基。

  摘要：

  在水环境中的有机反应最近已成为有前途的研究领域。首次描述了由分散的催化剂苄基溴的缓慢水解生成的新生HBr，其中内部水存在于含水表面活性剂中的受限胶束介质的疏水核中。持续释放的新生HBr能够以良好或极好的收率对碳水化合物，氨基醇和羟基化无环化合物中存在的酸敏感性正交官能团进行化学选择性切割。

  DOI：

  10.1021/acs.joc.9b02561
• 作为产物：
  描述：

  1,2:5,6-二-O-环己亚基-alpha-D-呋喃葡萄糖 在 溶剂黄146 作用下， 以65%的产率得到1,2-O-亚环己基-Alpha-D-呋喃葡萄糖
  参考文献：
  名称：

  使用糖衍生的醇盐作为手性促进剂的对映选择性 [1,2]-史蒂文斯重排

  摘要：

  通过使用新开发的 D-葡萄糖衍生的醇锂作为手性促进剂，实现了对映选择性碱基诱导的 [1,2]-史蒂文斯重排的第一个例子。这种重排提供了具有对映体富集形式的假季铵手性中心的α-氨基酮。

  DOI：

  10.1055/s-2008-1032107

文献信息

• Monosaccharide derivatives as anti-inflammatory agents
  申请人：Ranbaxy Laboratories Limited

  公开号：EP1953170A1

  公开（公告）日：2008-08-06

  The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disclosed herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory, cancer, cardiovascular and autoimmune diseases such as bronchial asthma, rheumatoid arthritis, type-I diabetes, multiple sclerosis, allograft rejection, psoriasis, inflammatory bowel disease, ulcerative colitis, acne, atherosclerosis, pruritis or allergic rhinitis. Pharmacological compositions containing compounds disclosed herein and the methods of treating diseases such as bronchial asthma, rheumatoid arthritis, type-I diabetes, multiple sclerosis, cancer, cardiovascular diseases, allograft rejection, psoriasis, inflammatory bowel disease, ulcerative colitis, acne, atherosclerosis, pruritis or allergic rhinitis and other inflammatory and/or autoimmune disorders, using the compounds are also provided.

  本发明涉及单糖衍生物作为抗炎药剂。本文披露的化合物可用于抑制和预防炎症及相关病理，包括炎症性、癌症、心血管和自身免疫疾病，如支气管哮喘、类风湿关节炎、I型糖尿病、多发性硬化症、移植排斥、牛皮癣、炎症性肠病、溃疡性结肠炎、痤疮、动脉粥样硬化、瘙痒或过敏性鼻炎。还提供了含有本文披露的化合物的药理组合物和治疗支气管哮喘、类风湿关节炎、I型糖尿病、多发性硬化症、癌症、心血管疾病、移植排斥、牛皮癣、炎症性肠病、溃疡性结肠炎、痤疮、动脉粥样硬化、瘙痒或过敏性鼻炎等疾病的方法，以及使用这些化合物治疗其他炎症性和/或自身免疫性疾病的方法。
• MONOSACCHARIDE DERIVATIVES
  申请人：Verma Ashwani Kumar

  公开号：US20080300196A1

  公开（公告）日：2008-12-04

  The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disclosed herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory, cancer, cardiovascular and autoimmune diseases such as bronchial asthma, rheumatoid arthritis, type-I diabetes, multiple sclerosis, allograft rejection, psoriasis, inflammatory bowel disease, ulcerative colitis, acne, atherosclerosis, pruritis or allergic rhinitis. Pharmacological compositions containing compounds disclosed herein and the methods of treating diseases such as bronchial asthma, rheumatoid arthritis, type-I diabetes, multiple sclerosis, cancer, cardiovascular diseases, allograft rejection, psoriasis, inflammatory bowel disease, ulcerative colitis, acne, atherosclerosis, pruritis or allergic rhinitis and other inflammatory and/or autoimmune disorders, using the compounds are also provided.

  本发明涉及单糖衍生物作为抗炎药物。本文披露的化合物可用于抑制和预防炎症及相关病理，包括炎症性、癌症、心血管和自身免疫疾病，如支气管哮喘、类风湿关节炎、I型糖尿病、多发性硬化症、移植排斥、牛皮癣、炎症性肠病、溃疡性结肠炎、痤疮、动脉粥样硬化、瘙痒或过敏性鼻炎。还提供了含有本文披露的化合物的药理组合物和治疗支气管哮喘、类风湿关节炎、I型糖尿病、多发性硬化症、癌症、心血管疾病、移植排斥、牛皮癣、炎症性肠病、溃疡性结肠炎、痤疮、动脉粥样硬化、瘙痒或过敏性鼻炎等疾病的方法，以及使用这些化合物治疗其他炎症和/或自身免疫性疾病的方法。
• The condensations of polyhydric alcohols and monosaccharides with cyclopentanone and cyclohexanone
  作者：V.M. Mićović、A. Stojiljković

  DOI：10.1016/0040-4020(58)88017-5

  日期：1958.1

  cyclohexanone have been shown to condense with polyhydric alcohols and monosaccharides to yield di- and tri-cyclopentylidene and cyclohexylidene derivatives. Series of new compounds with glycerol, pentaerythritol, mesoerythritol, arabitol, mannitol, sorbitol, xylose, arabinose, glucose, mannose and fructose have been prepared and characterised. In some instances attempts have been made to prove the structures

  环戊酮和环己酮已被证明与多元醇和单糖缩合，得到二-和三-环戊基和环亚己基衍生物。已经制备并表征了一系列新化合物，包括甘油，季戊四醇，中观赤藓糖醇，阿拉伯糖醇，甘露醇，山梨糖醇，木糖，阿拉伯糖，葡萄糖，甘露糖和果糖。在某些情况下，已经尝试证明所得产物的结构或为已经提出的结构提供一些实验证据。
• 1,3-Dipolar cycloaddition reaction of α,β-unsaturated esters and lactones with diazomethane
  作者：S. Baskaran、J. Vasu、Ram Prasad.K. Kodukulla、Girish K. Trivedi、J. Chandrasekhar

  DOI：10.1016/0040-4020(96)00099-3

  日期：1996.3

  1,3-Dipolar cycloaddition of diazomethane to the α,β-unsaturated esters and lactones such as 2–4, 6–8, 10 and 13 occurs in a stereoselective manner affording conjugated . E and Z isomers of D-mannitol lead to identical product which was cyclised to investigate the absolute stereochemistry of the product. the regiospecificities of all the reactions are consistent with FMO coefficients obtained through

  重氮化合物的1，3-偶极环加成至α，β-不饱和酯和内酯（例如2–4、6–8、10和13）以立体选择性方式发生，从而产生共轭。D-甘露醇的E和Z异构体产生相同的产物，将其环化以研究产物的绝对立体化学。所有反应的区域特异性与通过AM1计算获得的FMO系数一致。
• Identification of the furanose ring conformations and the factors driving their adoption
  作者：Dominik Walczak、Artur Sikorski、Daria Grzywacz、Andrzej Nowacki、Beata Liberek

  DOI：10.1016/j.carres.2023.108780

  日期：2023.4

  respectively, are presented. Conformational analysis of these furanoses is conducted based on the proton nuclear magnetic resonance (1H NMR) spectroscopy, density functional theory (DFT) calculations, and X-ray analysis. It is shown that the particular group of the presented furanoses is locked in the specific conformation. These are the 1T2-like, the 0E-like, and the 3T4-like conformation, respectively. Characteristic

  展示了三组分别在 C3-C4、C2-C3 和 C1-C2 键上旋转自由度受限的呋喃糖。这些呋喃糖的构象分析基于质子核磁共振 ( 1 H NMR) 光谱、密度泛函理论 (DFT) 计算和 X 射线分析进行。结果表明，所呈现的呋喃糖的特定组被锁定在特定的构象中。它们分别是1 T 2样、0 E样和3 T 4样构象。特点1介绍了这三种构象的 H NMR 光谱，并讨论了影响分析的呋喃糖构象偏好的因素。