N-叔丁氧羰基-L-苯乙烯基丙氨酸二环己胺盐 | 261165-04-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-叔丁氧羰基-L-苯乙烯基丙氨酸二环己胺盐
• 中文别名: (S)-2-(BOC-氨基)-5-苯基-4-戊烯酸；BOC-L-苯乙烯基甘氨酸二环己胺盐；(S)-n-boc-苯乙烯丙氨酸
• 英文名称: (S)-2-(tert-butyloxycarbonylamino)-5-phenylpent-4-enoic acid
• 英文别名: (2S)-2-[(tert-butoxycarbonyl)amino]-5-phenylpent-4-enoic acid；(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpent-4-enoic acid
• CAS: 261165-04-2
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: OIMOFNCGPRURIA-ZDUSSCGKSA-N

物化性质

• 沸点：
  433.35°C (rough estimate)
• 密度：
  1.1049 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn,N
• 危险类别码：
  R22,R51/53
• 危险品运输编号：
  UN 3077 9/PG 3
• 安全说明：
  S24/25,S61

SDS

Name:	(S)-N-BOC-Styrylalanine 95% (98% E.E.) Material Safety Data Sheet
Synonym:	(S)-N-tert-Butoxycarbonyl-2-Amino-5-Phenyl-4-Pentenoic Acid
CAS:	261165-04-2

Section 1 - Chemical Product MSDS Name:(S)-N-BOC-Styrylalanine 95% (98% E.E.) Material Safety Data Sheet
Synonym:(S)-N-tert-Butoxycarbonyl-2-Amino-5-Phenyl-4-Pentenoic Acid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
261165-04-2	(S)-N-BOC-Styrylalanine	95%	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
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. Wash mouth out with 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:
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
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. 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# 261165-04-2: 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: white to off-white
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: C16H21NO4
Molecular Weight: 291.34

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
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# 261165-04-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(S)-N-BOC-Styrylalanine - 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# 261165-04-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 261165-04-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 261165-04-2 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：

  N-叔丁氧羰基-L-苯乙烯基丙氨酸二环己胺盐 在 二苯二硫醚 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以95%的产率得到(S)-2-(tert-butyloxycarbonylamino)-5-phenylpent-4-enoic acid
  参考文献：
  名称：

  轻度相转移条件下的Wittig反应立体选择性合成不饱和和功能化的1-NHBoc氨基酸

  摘要：

  通过将熔融的三苯基膦与衍生自1-天冬氨酸的γ-碘NHBoc-氨基酯进行季铵化，描述了一种新的氨基酸phospho盐的立体选择性合成。羧酸官能团的脱保护得到带有游离羧酸基团的phospho盐是通过钯催化的脱盐基反应实现的。在固-液相转移条件下，在氯苯中，在K 3 PO 4存在下，该phospho盐用于与芳族或脂肪族醛和三氟苯乙酮的Wittig反应中作为弱碱，无需消旋即可得到相应的不饱和氨基酸。因此，与取代的醛的反应允许在氨基酸的侧链上接枝各种官能化的基团，例如三氟甲基，氰基，硝基，二茂铁基，硼酸钠基或叠氮基。另外，氨基酸Wittig试剂与α，β-不饱和醛的反应导致在侧链上带有二烯的氨基酸。最后，这种氨基酸phospho盐似乎是制备不饱和和非蛋白原性α-氨基酸的一种新的有力工具，可直接用于合成定制肽。

  DOI：

  10.1021/jo3013622

文献信息

• Stereoselective Synthesis of Unsaturated and Functionalized <scp>l</scp>-NHBoc Amino Acids, Using Wittig Reaction under Mild Phase-Transfer Conditions
  作者：Emmanuelle Rémond、Jérôme Bayardon、Marie-Joëlle Ondel-Eymin、Sylvain Jugé

  DOI：10.1021/jo3013622

  日期：2012.9.7

  afford the corresponding unsaturated amino acids without racemization. Thus, the reaction with substituted aldehydes allows to graft various functionalized groups on the lateral chain of the amino acid, such as trifluoromethyl, cyano, nitro, ferrocenyl, boronato, or azido. In addition, the reaction of the amino acid Wittig reagent with α,β-unsaturated aldehydes leads to amino acids bearing a diene on

  通过将熔融的三苯基膦与衍生自1-天冬氨酸的γ-碘NHBoc-氨基酯进行季铵化，描述了一种新的氨基酸phospho盐的立体选择性合成。羧酸官能团的脱保护得到带有游离羧酸基团的phospho盐是通过钯催化的脱盐基反应实现的。在固-液相转移条件下，在氯苯中，在K 3 PO 4存在下，该phospho盐用于与芳族或脂肪族醛和三氟苯乙酮的Wittig反应中作为弱碱，无需消旋即可得到相应的不饱和氨基酸。因此，与取代的醛的反应允许在氨基酸的侧链上接枝各种官能化的基团，例如三氟甲基，氰基，硝基，二茂铁基，硼酸钠基或叠氮基。另外，氨基酸Wittig试剂与α，β-不饱和醛的反应导致在侧链上带有二烯的氨基酸。最后，这种氨基酸phospho盐似乎是制备不饱和和非蛋白原性α-氨基酸的一种新的有力工具，可直接用于合成定制肽。