(R)-4-丁基-2-噁唑烷酮 | 158249-50-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: (R)-4-丁基-2-噁唑烷酮
• 英文名称: 4-Butyl-2-oxazolidinone
• 英文别名: (4R)-4-Butyl-2-oxazolidinone；(4R)-4-butyl-1,3-oxazolidin-2-one
• CAS: 158249-50-4
• 化学式: C₇H₁₃NO₂
• 分子量: 143.186
• InChiKey: XOTKVAZRWPADJP-ZCFIWIBFSA-N

物化性质

• 沸点：
  310.4±9.0 °C(Predicted)
• 密度：
  1.002±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

SDS

Name:	(4R)-4-Butyl-2-oxazolidinone Material Safety Data Sheet
Synonym:
CAS:	158249-50-4

Section 1 - Chemical Product MSDS Name:(4R)-4-Butyl-2-oxazolidinone Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
158249-50-4	(4R)-4-Butyl-2-oxazolidinone		unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause 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.
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 158249-50-4: 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: Powder
Color: white to light yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
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: C7H13NO2
Molecular Weight: 143.19

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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.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 158249-50-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(4R)-4-Butyl-2-oxazolidinone - 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# 158249-50-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 158249-50-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 158249-50-4 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：

  月桂酰氯 、 2-氯-2-氧-1,3,2-二氧磷杂环戊烷 、 (R)-4-丁基-2-噁唑烷酮 、 三甲胺 生成 (2-{[2-((S)-Dodecanoylamino)-hexyloxy]-hydroxy-phosphoryloxy}-ethyl)-trimethyl-ammonium
  参考文献：
  名称：

  Katsumura; Iwama; Inagaki, Russian Journal of Organic Chemistry, 1996, vol. 32, # 2, p. 225 - 229

  摘要：

  DOI：
• 作为产物：
  描述：

  (4R)-4-butyl-3-(dimethylamino)-1,3-oxazolidin-2-one 以73%的产率得到
  参考文献：
  名称：

  Matsubara Seijiro, Ukita Hideo, Kodama Tomohiro, Utimoto Kiitiro, Chem. Lett, (1994) N 5, S 831-834

  摘要：

  DOI：

文献信息

• A New Route for Protected Amino Alcohols from (<i>R</i>)-Glycidol. Copper(I) Mediated Alkylation of 4-Tosyloxymethyl-2-oxazolidinone
  作者：Seiji Iwama、Shigeo Katsumura

  DOI：10.1246/bcsj.67.3363

  日期：1994.12

  (S)-4-tosyloxymethyl-2-oxazolidinone, which was synthesized from (R)-glycidol through (R)-4-benzoyloxymethyl-2-oxazolidinone, with various lithium dialkylcuprate(I)s in THF proceeded smoothly to afford the corresponding protected amino alcohol derivatives in good yield.

  由（R）-缩水甘油经（R）-4-苯甲酰氧基甲基-2-恶唑烷酮合成的（S）-4-甲苯磺酰氧基甲基-2-恶唑烷酮与各种二烷基铜酸锂（I）在THF中的反应顺利进行以良好的收率得到相应的保护氨基醇衍生物。
• Diastereoselective Addition of Organometallic Reagents to Imines or Hydrazones Containing 1,3-Oxathiane As a Chiral Template
  作者：Seijiro Matsubara、Hideo Ukita、Tomohiro Kodama、Kiitiro Utimoto

  DOI：10.1246/cl.1994.831

  日期：1994.5

  The addition of organometallic reagents to imines or hydrazones containing 1,3-oxathiane as a chiral auxiliary proceeded with high diastereoselectivity and can be used as a key reaction for the preparation of chiral β-amino alcohols.

  将有机金属试剂添加到含有 1,3-氧杂噻吩作为手性助剂的亚胺或腙中，具有较高的非对映选择性，可作为制备手性 β-氨基醇的关键反应。
• Catalytic enantioselective synthesis of β-amino alcohols by nitrene insertion
  作者：Zijun Zhou、Yuqi Tan、Xiang Shen、Sergei Ivlev、Eric Meggers

  DOI：10.1007/s11426-020-9906-x

  日期：2021.3

  Chiral β-amino alcohols are important building blocks for the synthesis of drugs, natural products, chiral auxiliaries, chiral ligands and chiral organocatalysts. The catalytic asymmetric β-amination of alcohols offers a direct strategy to access this class of molecules. Herein, we report a general intramolecular C(sp3)-H nitrene insertion method for the synthesis of chiral oxazolidin-2-ones as precursors

  手性β-氨基醇是合成药物，天然产物，手性助剂，手性配体和手性有机催化剂的重要组成部分。醇的催化不对称β-氨基化提供了一种直接的策略来接近这类分子。在这里，我们报告了一般的分子内C（sp 3）-H氮烯插入方法，用于合成手性恶唑烷-2-酮作为手性β-氨基醇的前体。具体地，用2mol％的手性钌催化剂将N-苯甲酰氧基氨基甲酸酯的闭环C（sp 3）-H胺化提供环状氨基甲酸酯，产率高达99％，ee高达99％。该方法适用于苄基，烯丙基和炔丙基CH键，甚至可以应用于完全未活化的C（sp 3）-H键，尽管产率和立体选择性有所降低。随后可以将获得的环状氨基甲酸酯水解以获得手性β-氨基醇。该方法非常实用，因为该催化剂可以很容易地以克规模合成，并且可以在反应后再循环以进一步使用。新方法的合成价值通过不对称合成手性恶唑烷-2--2-酮作为中间体来合成天然产物金葡糖醇和手性β-氨基醇，它们是合成手性氨基酸的中间体，茚
• Matsubara Seijiro, Ukita Hideo, Kodama Tomohiro, Utimoto Kiitiro, Chem. Lett, (1994) N 5, S 831-834
  作者：Matsubara Seijiro, Ukita Hideo, Kodama Tomohiro, Utimoto Kiitiro

  DOI：——

  日期：——
• SYNTHESIS OF<i>N</i>-PROTECTED 2-AMINOHEXANESULFONIC ACID
  作者：Violetta Constantinou-Kokotou

  DOI：10.1080/00304949909355723

  日期：1999.4