(2R,3S)-N-苄氧羰基-2,3-二苯基吗啉-6-酮 | 100516-54-9

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: (2R,3S)-N-苄氧羰基-2,3-二苯基吗啉-6-酮
• 中文别名: 2R,3S-N-CBZ-2,3-二苯基吗啉-6-酮；(2R,3S)-(-)-6-酮-2,3-二苯基-4-吗啡啉甲酸苄酯；苄基(2R,3S)-(-)-6-氧-2,3-二苯基-4-吗啉E甲酸；(2R,3S)-2,3-二苯基-6-氧代吗啉-4-甲酸苄酯
• 英文名称: (5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
• 英文别名: benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate；William's lactone；(5S,6R)-4-(benzyloxy-carbonyl)-5,6-diphenyl-morpholin-2-one；(2R,3S)-Benzyl 6-oxo-2,3-diphenylmorpholine-4-carboxylate；benzyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate
• CAS: 100516-54-9
• 化学式: C₂₄H₂₁NO₄
• mdl: MFCD00074958
• 分子量: 387.435
• InChiKey: HECRUWTZAMPQOS-XZOQPEGZSA-N

物化性质

• 熔点：
  205-207 °C(lit.)
• 比旋光度：
  -66 º (c=5.5 in methylene chloride)
• 沸点：
  583.5±50.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（轻微）、二氯甲烷（轻微）、DMSO（轻微）
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，未有已知危险反应。应避免与强氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  29349990
• 安全说明：
  S26,S37/39
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将贮藏器密封，并存放在阴凉、干燥的地方。确保工作环境有良好的通风或排气设施。最好在2°C至8°C的温度下保存。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
: (2R,3S)-(−)-N-Z-6-oxo-2,3-diphenylmorpholine
Product name
CAS-No. : 100516-54-9
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S37/39 Wear suitable gloves and eye/face protection.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
: Benzyl (2R,3S)-(−)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate
Synonyms
Formula : C24H21NO4
Molecular Weight : 387,43 g/mol
Component Concentration
(2R,3S)-(-)-N-Z-6-oxo-2,3-diphenylmorpholine
CAS-No. 100516-54-9 -

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: 2 - 8 °C
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Immersion protection
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: > 480 min
Material tested:Dermatril® ( Z677272, Size M)
Splash protection
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: > 30 min
Material tested:Dermatril® ( Z677272, Size M)
data source: KCL GmbH, D-36124 Eichenzell, phone [phone], test method: EN374
If used in solution, or mixed with other substances, and under conditions which differ from EN 374,
contact the supplier of the CE approved gloves. This recommendation is advisory only and must
be evaluated by an Industrial Hygienist familiar with the specific situation of anticipated use by our
customers. It should not be construed as offering an approval for any specific use scenario.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 205 - 207 °C - lit.
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation
May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  (2R,3S)-N-苄氧羰基-2,3-二苯基吗啉-6-酮 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 0.75h， 以100%的产率得到(3S,5S,6R)-4-(benzyloxycarbonyl)-3-bromo-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
  参考文献：
  名称：

  Practical asymmetric syntheses of .alpha.-amino acids through carbon-carbon bond constructions on electrophilic glycine templates

  摘要：

  DOI：

  10.1021/ja00213a031
• 作为产物：
  描述：

  ALPHA-安息香肟 在 palladium on activated charcoal 氢气 、 碳酸氢钠 、 对甲苯磺酸 、 三乙胺 作用下， 生成 (2R,3S)-N-苄氧羰基-2,3-二苯基吗啉-6-酮
  参考文献：
  名称：

  Chiral synthesis of L-γ-carboxyglutamic acid (L-Gla)

  摘要：

  A two step synthesis involving the use of a chiral template, benzyl (2R, 3S)-(-)-6-oxo-2,3-diphenyl-4-morpholine-carboxylate(3) (5a); provides orthogonally protected L-Gla (9) in 60% overall yield (>99% ee), with no resolution required.

  DOI：

  10.1016/0040-4039(94)02418-b

文献信息

• An efficient asymmetric synthesis of L-α,ω-diaminoalkanoic acids
  作者：Zhengxin Dong

  DOI：10.1016/0040-4039(93)88028-h

  日期：1992.12

  Efficient asymmetric syntheses of L-2,7-diaminoheptanoic acid and L-2,8-diaminooctanoic acid are described.

  描述了L -2，7-二氨基庚酸和L -2，8-二氨基辛酸的有效的不对称合成。
• An Improved Synthesis of Optically Pure 4-Boc-5,6-Diphenylmorpholin-2-one and 4-Cbz-5,6-Diphenylmorpholin-2-one
  作者：Robert M. Williams、Kim A. Dastlik、Uta Sundermeier、Deidre M. Johns、Yuyin Chen

  DOI：10.1055/s-2005-863740

  日期：——

  A convenient synthesis of optically pure 4-Boc-5,6-diphenylmorpholin-2-one and 4-Cbz-5,6-diphenylmorpholin-2-one by reaction of (+)- or (-)-2-amino-1,2-diphenylethanol with ethyl bromoacetate, followed by N-protection, and p-TsOH-mediated ring-closure is described. The title compounds can be used as synthons for the asymmetric synthesis of N-protected α-amino acids. These lactones are quite stable

  通过 (+)- 或 (-)-2-amino-1 反应方便合成光学纯 4-Boc-5,6-diphenylmorpholin-2-one 和 4-Cbz-5,6-diphenylmorpholin-2-one , 2-二苯基乙醇与溴乙酸乙酯, 然后是 N-保护, 和 p-TsOH 介导的闭环。标题化合物可用作合成子，用于 N-保护的 α-氨基酸的不对称合成。这些内酯对于储存和处理非常稳定。
• Stereoselective Synthesis of (2R,5R)- and (2S,5R)-5-Hydroxylysine
  作者：Adrianus M. C. H. van den Nieuwendijk、Nicole M. A. J. Kriek、Johannes Brussee、Jacques H. van Boom、Arne van der Gen

  DOI：10.1002/1099-0690(200011)2000:22<3683::aid-ejoc3683>3.0.co;2-u

  日期：2000.11

  A stereoselective synthesis of (2S,5R)-5-hydroxylysine (1) and (2R,5R)-5-hydroxylysine (17), based on a concept involving Williams glycine template methodology and (R)-hydroxynitrile lyase for the introduction of chirality at the α-position and the side-chain, respectively, is described. This strategy offers an expeditious route towards orthogonally protected 5-hydroxylysines.

  （2 S，5 R）-5-羟基赖氨酸（1）和（2 R，5 R）-5-羟基赖氨酸（17）的立体选择性合成，基于涉及威廉姆斯甘氨酸模板法和（R）-羟基腈裂解酶的概念描述了分别在α位和侧链引入手性的方法。这种策略为正交保护的5-羟基赖氨酸提供了一条快捷途径。
• An efficient asymmetric synthesis of (2S,3S)- and (2R,3R)-β-hydroxyornithine
  作者：Duane E DeMong、Robert M Williams

  DOI：10.1016/s0040-4039(00)01945-6

  日期：2001.1

  Asymmetric syntheses of (2S,3S)- and (2R,3R)-β-hydroxyornithine have been achieved in four steps and 46% overall yield. The key step in this synthesis involved an aldol reaction between a chiral glycine boron enolate and (3-oxo-propyl)-carbamic acid benzyl ester.

  （2 S，3 S）-和（2 R，3 R）-β-羟基鸟氨酸的不对称合成已通过四个步骤完成，总收率达46％。该合成的关键步骤涉及手性甘氨酸烯醇硼烯酸酯和（3-氧代-丙基）-氨基甲酸苄酯之间的醛醇缩合反应。
• A Total Synthesis of Hydroxylysine in Protected Form and Investigations of the Reductive Opening of <i>p</i>-Methoxybenzylidene Acetals
  作者：Tomas Gustafsson、Magnus Schou、Fredrik Almqvist、Jan Kihlberg

  DOI：10.1021/jo049136w

  日期：2004.12.1

  A synthesis of (2S,5R)-5-hydoxylysine, based on (R)-malic acid and Williams glycine template as chiral precursors, has been developed. This afforded hydroxylysine, suitably protected for direct use in peptide synthesis, in 32% yield over the 13-step sequence. Regioselective reductive opening of a p-methoxybenzylidene acetal and alkylation of the Williams glycine template were key steps in the synthetic

  （2的合成小号，5 - [R）-5- hydoxylysine，基于（[R ）-苹果酸和Williams甘氨酸模板作为手性前体，已经研制成功。这样得到的羟基赖氨酸经过适当保护，可直接用于肽合成，在13步序列中的收率为32％。对甲氧基亚苄基乙缩醛的区域选择性还原打开和威廉姆斯甘氨酸模板的烷基化是合成序列中的关键步骤。出人意料的是，p开口处的区域选择性与预期相比，将-甲氧基亚苄基缩醛逆转。发现这是由于在还原开口中用作亲电子试剂的三烷基甲硅烷基氯化物与相邻的叠氮化物官能团的螯合。还发现在反应中形成了等量的三烷基甲硅烷基氢化物，这一发现导致对用氰基硼氢化钠作为还原剂的对-甲氧基亚苄基乙缩醛的还原开口的进一步机理研究。