(3R-顺)-(-)-3-苯基四氢吡咯并-[2,1-B]唑-5(6H)-酮 | 133007-27-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (3R-顺)-(-)-3-苯基四氢吡咯并-[2,1-B]唑-5(6H)-酮
• 中文别名: (3R-顺)-(-)-3-苯基四氢吡咯并-[2,1-b]噁唑-5(6H)-酮
• 英文名称: (3R,7aS)-3-phenyl-2,3,5,6,7,7a-hexahydropyrrolo[2,1-b]oxazol-5-one
• 英文别名: (3R,7AS)-3-phenyltetrahydropyrrolo[2,1-b]oxazol-5(6H)-one；(3R,7aS)-3-phenyl-3,6,7,7a-tetrahydro-2H-pyrrolo[2,1-b][1,3]oxazol-5-one
• CAS: 133007-27-9
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: CQPBRZXBXFZYBD-JQWIXIFHSA-N

物化性质

• 熔点：
  76-80 °C
• 沸点：
  341.55°C (rough estimate)
• 密度：
  1.1255 (rough estimate)
• 稳定性/保质期：
  遵循规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S36/37
• 危险类别码：
  R20/21/22
• 储存条件：
  存放于阴凉干燥处。

SDS

Name:	(3R-Cis)-(-)-3-Phenyltetrahydropyrrolo-[2 1-B]Oxazol-5(6H)-One 97% Material Safety Data Sheet
Synonym:	None Known
CAS:	133007-27-9

Section 1 - Chemical Product MSDS Name:(3R-Cis)-(-)-3-Phenyltetrahydropyrrolo-[2 1-B]Oxazol-5(6H)-One 97% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
133007-27-9	(3R-Cis)-(-)-3-Phenyltetrahydropyrrolo	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.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. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
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# 133007-27-9: 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 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: Solid
Color: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 76-77 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: C13H13NO2
Molecular Weight: 215.0965

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 133007-27-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(3R-Cis)-(-)-3-Phenyltetrahydropyrrolo-[2,1-B]Oxazol-5(6H)-One - 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
No information available.
IMO
No information available.
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: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 36/37 Wear suitable protective clothing and
gloves.
WGK (Water Danger/Protection)
CAS# 133007-27-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 133007-27-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 133007-27-9 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：

  (3R-顺)-(-)-3-苯基四氢吡咯并-[2,1-B]唑-5(6H)-酮 在 甲酸铵 、 palladium(II) hydroxide 、 sodium hydride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 14.0h， 生成 (3R,3'R,7a'S)-6-amino-3'-phenyl-2',3',7',7a'-tetrahydro-5'H-spiro[indoline-3,6'-pyrrolo[2,1-b]oxazole]-2,5'-dione
  参考文献：
  名称：

  通过手性助剂（双环内酰胺）控制的S N Ar反应 对螺氧基吲哚的对映选择性合成†

  摘要：

  开发了一种高效的手性酰基双环内酰胺与取代的2,4-二硝基苯的对映选择性S N Ar反应，提供了含有季铵立体异构中心的产物。它们进一步用于螺氧代吲哚的对映选择性合成。

  DOI：

  10.1039/c0ob00661k
• 作为产物：
  描述：

  (3R,5R,7aS)-3-phenyl-2,3,5,6,7,7a-hexahydropyrrolo[2,1-b][1,3]oxazole-5-carbonitrile 在 potassium permanganate 作用下， 以 水 、 丙酮 为溶剂， 反应 12.0h， 以94%的产率得到(3R-顺)-(-)-3-苯基四氢吡咯并-[2,1-B]唑-5(6H)-酮
  参考文献：
  名称：

  N-(氰甲基)恶唑烷系统的还原和氧化转化以扩大哌啶的手性库

  摘要：

  已利用两种新反应来修饰含有手性、非外消旋 N-（氰甲基）恶唑烷系统的哌啶支架。首先研究了雷尼镍介导的脱氰作用，然后是使用高锰酸钾的氧化过程，以提供对映体纯内酰胺，包括氧代哌啶酸衍生物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200400404

文献信息

• A simple asymmetric synthesis of 2-substituted pyrrolidines from 3-acylpropionic acids
  作者：A. I. Meyers、Laurence E. Burgess

  DOI：10.1021/jo00007a011

  日期：1991.3

  The title compounds have been prepared from 3-acylpropionic acids 2 and (-)-R-phenylglycinol in a three-step sequence in > 98% enantiomeric excess. The R group in 2 ultimately becomes the 2-substituent in the chiral pyrrolidine.
• An asymmetric synthesis of the key precursor to (−)-indolizomycin
  作者：Michael D. Groaning、A.I. Meyers

  DOI：10.1016/s0040-4039(99)00728-5

  日期：1999.6

  Using chiral bicyclic lactams, containing an alpha,beta-unsaturation, the key precursor of (-)-indolizomycin was obtained in optically pure form. The sequence involved a >20:1 diastereoselective cyclopropanation of the unsaturated lactam 5 employing sulfoxonium methylide. TiCl4 mediated addition of allyltrimethylsilane afforded pyrrolidone 7 in a diastereomeric ratio of >20:1. The appropriately substituted pyrrolidone 2 was prepared by debenzylation and subsequent alkylation with 3-bromoproponic ester. The six step sequence from commercially available starting materials was performed in 26% overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Diastereoselective bis-alkylation of chiral non-racemic α,β-unsaturated γ-lactams
  作者：Isabelle Baussanne、Angèle Chiaroni、Henri-Philippe Husson、Claude Riche、Jacques Royer

  DOI：10.1016/s0040-4039(00)76705-0

  日期：1994.6

  A new chiral non-racemic gamma-lactam 1 easily prepared in one step from (R)-(-)-phenylglycinol was bis-alkylated alpha to the carbonyl function in very high to complete diastereoselectivity. The stereochemistry at the so-formed chiral quaternary center was ascertained through an X-ray crystallographic study.
• Asymmetric synthesis of 5-substituted pyrrolidinones via a chiral N-acyliminium equivalent
  作者：Isabelle Baussanne、Angèle Chiaroni、Jacques Royer

  DOI：10.1016/s0957-4166(01)00195-1

  日期：2001.5

  5-Substituted pyrrolidinones 5 were synthesized in good yields and with fair to good diastereoselectivities from the chiral non-racemic oxazolopyrrolidinone 4. Various nucleophiles including cuprates, silanes and phosphites were used. The chiral induction is thought to arise from a chelated N-acyliminium species. (C) 2001 Elsevier Science Ltd. All rights reserved.
• MEYERS, A. I.;BURGESS, LAURENCE E., J. ORG. CHEM., 56,(1991) N, C. 2294-2296
  作者：MEYERS, A. I.、BURGESS, LAURENCE E.

  DOI：——

  日期：——