4-苄基-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-十三氟辛基)-1,3-恶唑烷-2-酮 | 857637-92-4

• 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: 4-苄基-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-十三氟辛基)-1,3-恶唑烷-2-酮
• 中文别名: (4S,5R)-(-)-4-苄基-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-十三氟辛基)-2-恶唑烷酮,99；(4S,5R)-(-)-4-苄基-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-十三氟辛基)-2-恶唑烷酮,99%
• 英文名称: (4S,5R)-4-benzyl-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone
• 英文别名: (4S,5R)-4-benzyl-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-1,3-oxazolidin-2-one
• CAS: 857637-92-4
• 化学式: C₁₈H₁₄F₁₃NO₂
• 分子量: 523.294
• InChiKey: LPSJVRKHQCWHPG-WDEREUQCSA-N

物化性质

• 熔点：
  90-95°C
• 比旋光度：
  -32.2° (c 1.09, CHCl3)
• 沸点：
  421.8±40.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  15

SDS

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Section 1: Product Identification
Chemical Name: (4S,5R)-(-)-4-Benzyl-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl-2-oxazolidinone, 99%
CAS Registry Number: 857637-92-4
Formula: C18H14F13NO2
EINECS Number: none
Chemical Family: organic amine
Synonym: (4S,5R)-(-)-4-Benzyl-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl)-oxazolidin-2-one

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 857637-92-4 100% 2.5mg/m3 (as F) 2.5mg/m3 (as F)

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Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract.
Primary Routes of Exposure: Ingestion, inhalation, skin, eyes
Eye Contact: Causes irritation of the eyes.
Skin Contact: Causes 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.
Product contains fluorine which under certain conditions of use, decomposition, or metabolism, may generate
Chronic Health Affects: fluoride ion, causing, nausea, vomiting, labored breathing, hypocalcaemia, deterioration of bone and tooth
structure, kidney and liver damage.
NTP: No
IARC: No
OSHA: No

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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.

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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 toxic and irritating fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards.

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

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

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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.

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SECTION 9: Physical and Chemical Properties
Color and Form: white powder
Molecular Weight: 523.29
Melting Point: 90-95°
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: not determined
Solubility in Water: insoluble

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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, carbonyl fluoride, nitrogen oxides and organic fumes

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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

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SECTION 12: Ecological Information
Ecological Information: No information available

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

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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

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SECTION 15: Regulatory Information
TSCA: Not listed in the TSCA inventory
SARA (Title 313): Title compound not listed
Second Ingredient: Not listed in the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-苄基-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-十三氟辛基)-1,3-恶唑烷-2-酮 在 氧气 三乙基硼 、 三正丁基氢锡 、 氯化锆(IV) 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 (4S,5R)-4-benzyl-3-(butanoyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone
  参考文献：
  名称：

  Stereoselective Conjugate Radical Additions:  Application of a Fluorous Oxazolidinone Chiral Auxiliary for Efficient Tin Removal

  摘要：

  A series of asymmetric free-radical-mediated intermolecular conjugate additions using a fluorous oxazolidinone chiral auxiliary has been completed. The fluorous auxiliary facilitated product isolation using fluorous solid phase extractions (FSPE), effectively removing excess organic and organometallic reagents. Parallel reactions carried out with a similar but nonfluorous norephedrine-derived oxazoldinone demonstrated the superior stereoselectivity and purification obtainable with the fluorous chiral auxiliary.

  DOI：

  10.1021/ol050956k
• 作为产物：
  描述：

  (S)-methyl 2-((ethoxycarbonyl)amino)-3-phenylpropanoate 在 sodium hydride 、 magnesium 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 32.0h， 生成 4-苄基-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-十三氟辛基)-1,3-恶唑烷-2-酮
  参考文献：
  名称：

  Practical Synthesis of Fluorous Oxazolidinone Chiral Auxiliaries from α-Amino Acids

  摘要：

  A series of new fluorous-supported oxazolidinone chiral auxiliaries has been prepared using a versatile and general five-step pathway, starting from readily available chiral a-amino acids. The key feature of this synthesis is the efficient generation of a suitably active perfluoroalkyllithium species. By use of this protocol, the auxiliaries can be obtained in high enantiomeric purity and on multigram scales from L-phenylalanine and L-valine with overall yields as high as 55%. The new methodology also incorporates fluorous solid-phase extraction on the large scale, allowing bulk quantities (up to 25 g) of fluorous compounds to be purified from the crude reaction mixture.

  DOI：

  10.1021/jo051696n

文献信息

• WO2006/96994
  申请人：——

  公开号：——

  公开（公告）日：——
• Recyclable supports for stereoselective 1,3-dipolar cycloadditions: application of a fluorous oxazolidinone chiral auxiliary
  作者：Jason E. Hein、Philip G. Hultin

  DOI：10.1016/j.tetasy.2005.05.041

  日期：2005.7

  The utility of a new fluorous-supported chiral auxiliary was tested using a series of catalyzed and uncatalyzed 1,3-dipolar cycloaddition reactions with diphenylnitrone. The yields and selectivities of the cycloadducts compare favourably with those obtained using the conventional Evans-type auxiliaries, while purification was greatly assisted by using fluorous solid phase extraction. Following characterization, the cycloadducts were released from the auxiliaries by reductive cleavage. The auxiliary was readily refunctionalized and reused in subsequent cycloaddition reactions, with no deterioration of the observed yields or selectivities. (c) 2005 Elsevier Ltd. All rights reserved.