(S)-(-)-1-(2-呋喃基)乙醇 | 85828-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: (S)-(-)-1-(2-呋喃基)乙醇
• 英文名称: (-)-α-(2-Furyl)ethyl acetate
• 英文别名: (S)-1-(furan-2-yl)ethyl acetate；(S)-1-(2-furyl)ethyl ethanoate；(S)-1-acetoxy-1-[2]furyl-ethane；(S)-1-Acetoxy-1-[2]furyl-aethan；S(-)-1-(2-furyl)ethanol；[(1S)-1-(furan-2-yl)ethyl] acetate
• CAS: 85828-09-7
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: WOYASPSVTWXGJJ-LURJTMIESA-N

物化性质

• 沸点：
  60-61 °C8 mm Hg(lit.)
• 密度：
  1.078 g/mL at 20 °C(lit.)
• 闪点：
  110 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932190090

SDS

Name:	(s)-(-)-1-(2-Furyl)ethanol stabilized 99% Material Safety Data Sheet
Synonym:	(S)-(-)-alpha-Methylfuran-2-methano
CAS:	85828-09-7

Section 1 - Chemical Product MSDS Name:(s)-(-)-1-(2-Furyl)ethanol stabilized 99% Material Safety Data Sheet
Synonym:(S)-(-)-alpha-Methylfuran-2-methano

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
85828-09-7	(S)-(-)-1-(2-Furyl)ethanol	99%	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Light sensitive.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May be harmful if absorbed through the skin.
Ingestion:
May be harmful if swallowed.
Inhalation:
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.
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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable 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 tightly closed container. Store in a dry area. Deep freeze (below -20C). Store protected from light.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 85828-09-7: 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: Clear liquid
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 61 - 62 deg C @ 10 mmHg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Soluble.
Specific Gravity/Density: 1.078
Molecular Formula: C6H8O2
Molecular Weight: 112.13

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Light.
Incompatibilities with Other Materials:
Not available.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 85828-09-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(S)-(-)-1-(2-Furyl)ethanol - 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
No information available.

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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# 85828-09-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 85828-09-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 85828-09-7 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：

  重氮甲烷 、 (S)-(-)-1-(2-呋喃基)乙醇 在 四氧化钌 sodium periodate 作用下， 生成 2-(S)-乙酰氧基丙酸甲酯
  参考文献：
  名称：

  Ruthenium tetroxide catalyzed oxidations of aromatic and heteroaromatic rings

  摘要：

  DOI：

  10.1021/jo00162a009
• 作为产物：
  描述：

  DL-1-(2-呋喃基)乙基乙酸酯 在 Candida antarctica lipase immobilised on acrylic resin CAL-B 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以45%的产率得到(S)-(-)-1-(2-呋喃基)乙醇
  参考文献：
  名称：

  通过 CAL-B/Na2CO3-脱酰和 Mitsunobu 反应方案实际获得 (S)-杂环芳香族乙酸酯

  摘要：

  摘要 在此，我们报道了对映体纯形式的 2,3-二氢苯并呋喃-3-醇 ( 1 )、苯并二氢吡喃-4-醇 ( 2 )、苯并二氢吡喃-4-醇 ( 3 )、1-(呋喃-2-基)的制备) 乙醇 ( 5 ) 和 1-(噻吩-2-基) 乙醇 ( 6 )，通过有机介质中南极假丝酵母脂肪酶B /Na 2 CO 3水解序列催化的动力学拆分。(R)-提供的醇和( S)-剩余的乙酸酯被回收为对映体纯物(ee >99%，E ≫ 200，转化率 = 50%）。这些理想的酶动力学分辨率 (EKR) 很好地融入到 Mitsunobu 反转方案中，在一锅程序中得到良好到高对映体过量 (88%–92% ee) 的(S)-杂环乙酸酯 ( 1a–3a )。同时，(S)-杂芳族乙酸酯（5a和6a）具有适度的对映体过量（51%–62% ee）。所有(S)-乙酸酯均具有良好的分离化学收率 (>80%)，从而克服了常规动力学拆分过程中通常可以达到的最大

  DOI：

  10.1080/10242422.2022.2030726

文献信息

• A Divergent Synthesis of Uncommon Sugars from Furanaldehyde
  作者：Peng Wang、Lizhi Zhu、Arindam Talukdar、Guisheng Zhang、James Kedenburg

  DOI：10.1055/s-2005-869846

  日期：——

  A practical synthetic strategy has been developed for producing uncommon sugars. This method employed kinetic enzymatic resolution of 1-(2-furyl)ethanol, and followed by NBS-mediated Achmatowicz rearrangement to construct α,β-unsaturated lactones. After further derivatization, five representative uncommon sugar units were successfully synthesized.

  已经开发出一种实用的合成策略来生产稀有糖。该方法采用1-(2-呋喃基)乙醇的动力学酶解法，接着通过NBS介导的Achmatowicz重排构建α,β-不饱和内酯。经过进一步衍生化，成功合成了五个代表性的稀有糖单元。
• Asymmetric Hydrogenation of Itaconic Acid and Enol Acetate Derivatives with the Rh-TangPhos Catalyst
  作者：Wenjun Tang、Duan Liu、Xumu Zhang

  DOI：10.1021/ol0272592

  日期：2003.1.1

  [reaction: see text] The Rh-TangPhos catalyst has been used for asymmetric hydrogenation of itaconic acid and enol acetate derivatives. A variety of chiral 2-substituted succinic acids and chiral acetates have been obtained in excellent ee values (up to 99% ee).

  [反应：见正文] Rh-TangPhos催化剂已用于衣康酸和烯醇乙酸酯衍生物的不对称氢化。已经获得了各种具有出色ee值（最高ee为99％）的手性2-取代的琥珀酸和手性乙酸酯。
• Entrapment of Pseudomonas cepacia lipase with peracetylated β-cyclodextrin in sol–gel: application to the kinetic resolution of secondary alcohols
  作者：Ashraf Ghanem、Volker Schurig

  DOI：10.1016/s0957-4166(03)00550-0

  日期：2003.9

  cepacia lipase with peracetylated β-cyclodextrin was immobilized by the sol–gel process. The gel-entrapped lipase/cyclodextrin was prepared by the hydrolysis of methyltrimethoxysilane (MTMS) in the presence of the co-lyophilized lipase with peracetylated β-cyclodextrin prepared with different weight ratios (enzyme to CD). This type of enzyme preparation was subsequently used in the kinetic resolution

  共冻干洋葱假单胞菌过乙酰化β-环糊精的脂肪酶通过溶胶-凝胶法固定化。凝胶包裹的脂肪酶/环糊精是在共冻干脂肪酶与过乙酰化的β-环糊精共存的条件下，通过甲基三甲氧基硅烷（MTMS）的水解而制得的，所述过乙酰化的β-环糊精以不同的重量比（酶与CD）制备。这种类型的酶制剂随后用于动力学拆分一组仲醇，其中乙酸异丙烯酯作为甲苯中无害的酰基供体，作为有机介质。使用气相色谱法在新的手性固定相（CSP）Chirasil-β-Dex上含有十一碳亚甲基间隔基（C11-Chirasil-Dex）的情况下，在不进行衍生化的情况下，将分析中得到的手性醇（底物）和相应的乙酸盐（产物）进行基线分离。 。
• Highly Enantioselective Hydrogenation of Enol Acetates Catalyzed by Ru−TunaPhos Complexes
  作者：Shulin Wu、Weimin Wang、Wenjun Tang、Min Lin、Xumu Zhang

  DOI：10.1021/ol027010k

  日期：2002.12.1

  chiral disphosphines with tunable dihedral angles (TunaPhos) have been used for asymmetric hydrogenation of enol acetates and dihedral-angle-dependent enantioselectivities were observed. C2-TunaPhos has been proved to be effective for Ru-catalyzed asymmetric hydrogenation of electron-deficient and other enol acetates.

  [反应：见正文]具有可调二面角的手性二膦酸（TunaPhos）已用于烯醇乙酸酯的不对称氢化，并观察到二面角依赖性的对映选择性。事实证明，C2-TunaPhos可有效用于Ru催化的缺电子和其他烯醇乙酸酯的不对称加氢反应。
• Lipase-catalysed kinetic resolutions of secondary alcohols in pressurised liquid hydrofluorocarbons
  作者：Anthony J. Ball、Stuart Corr、Jason Micklefield

  DOI：10.1016/j.tetlet.2009.03.037

  日期：2009.7

  Three model secondary alcohols have been subjected to enzymatic kinetic resolution using three common lipases and a typical acyl donor. The resolutions were performed in two pressurised low-boiling hydrofluorocarbons, which are novel media for enzymatic reactions, and five conventional organic solvents. In general, higher yields, ee’s and rates of reaction were observed in the hydrofluorocarbons.

  使用三种常见的脂肪酶和典型的酰基供体，对三种模型仲醇进行了酶促动力学拆分。在两种加压的低沸点碳氢化合物（是酶促反应的新介质）和五种常规有机溶剂中进行拆分。通常，在氢氟烃中观察到较高的产率，ee和反应速率。