甲基(2E,4S)-(-)-4-(苯甲氧基)戊基-2-烯酸 | 112489-57-3

• 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: 甲基(2E,4S)-(-)-4-(苯甲氧基)戊基-2-烯酸
• 英文名称: (E)-(S)-[MeCH(OCH2C6H5)CHCHCO2Me]
• 英文别名: methyl (2E,4S)-4-benzyloxypent-2-enoate；(S,E)-Methyl 4-(benzyloxy)pent-2-enoate；methyl (E,4S)-4-phenylmethoxypent-2-enoate
• CAS: 112489-57-3
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: HQXFTCDXKMAFJW-FBOQAHMBSA-N

物化性质

• 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)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2918990090

SDS

Name:	Methyl(2E 4S)-(-)-4-(phenylmethoxy)pent-2-enoate Material Safety Data Sheet
Synonym:	None
CAS:	112489-57-3

Section 1 - Chemical Product MSDS Name:Methyl(2E 4S)-(-)-4-(phenylmethoxy)pent-2-enoate Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
112489-57-3	Methyl(2E,4S)-(-)-4-(phenylmethoxy)pen	100	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.Moisture sensitive.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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:
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 agent most appropriate to extinguish fire. Do NOT get water inside containers. 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:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Provide ventilation. Do not get water inside containers.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed.
Avoid ingestion and inhalation. Do not allow contact with water. Wash clothing before reuse. Keep from contact with moist air and steam.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.) Store protected from moisture.

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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# 112489-57-3: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: Not available.
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 applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: soluble in methanol, diethylether, thf
Specific Gravity/Density:
Molecular Formula:
Molecular Weight: 220.27

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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:
Moisture, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 112489-57-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl(2E,4S)-(-)-4-(phenylmethoxy)pent-2-enoate - 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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 37/39 Wear suitable gloves and eye/face
protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 112489-57-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 112489-57-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 112489-57-3 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：

  甲基(2E,4S)-(-)-4-(苯甲氧基)戊基-2-烯酸 在 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 lithium bromide 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 13.0h， 生成 (1E,3E,5S)-(-)-5-phenylmethoxy-1-phenylsulfonylhexa-1,3-diene
  参考文献：
  名称：

  通过高度富含对映体平面手性1-苯磺酰基取代的三羰基（“手性转移”在铁介导dienylic取代η 5 -戊二烯基）铁（1 +）配合物

  摘要：

  的制备高度diastereo-和对映体富集的手性平面1-苯磺酰基取代的三羰基（η 5 -戊二烯基）铁（1 +）络合物7 [顺式，顺式- （1- [R，5 - [R ）- 7和SYN，SYN - （ 1 S，5 S）-7（顺式或U形）; DE > 99％5-顺式-CH 3 / 5-抗-CH 3 ⪢100：1，EE> 99％; 数量的87％描述了来自解析的6 ]。从对映纯二烯（1ë，3 E，S） - 5的阳离子络合物的两种对映体顺式，顺式- 7成为通过相应的中性三羰基的非对映混合物的色谱拆分容易获得（η 4 -二烯）合铁（0）配合物6 [（1- [R，5小号） - 6 ψ-内切- 6和（1级小号，5小号） - 6 ψ-外型- 6 ; de > 99％，ee> 99％；定量的85％解决之前]。杂原子和碳原子亲核试剂（吗啉，甲硅烷基烯醇醚8和甲硅烷基烯酮缩醛9）的亲核加成到外消旋复合物syn，syn-（1

  DOI：

  10.1016/s0022-328x(96)06850-7
• 作为产物：
  描述：

  乙基(S)-2-(苄氧基)丙酸酯 在 二异丁基氢化铝 、 三乙胺 、 lithium bromide 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 13.0h， 生成 甲基(2E,4S)-(-)-4-(苯甲氧基)戊基-2-烯酸
  参考文献：
  名称：

  通过高度富含对映体平面手性1-苯磺酰基取代的三羰基（“手性转移”在铁介导dienylic取代η 5 -戊二烯基）铁（1 +）配合物

  摘要：

  的制备高度diastereo-和对映体富集的手性平面1-苯磺酰基取代的三羰基（η 5 -戊二烯基）铁（1 +）络合物7 [顺式，顺式- （1- [R，5 - [R ）- 7和SYN，SYN - （ 1 S，5 S）-7（顺式或U形）; DE > 99％5-顺式-CH 3 / 5-抗-CH 3 ⪢100：1，EE> 99％; 数量的87％描述了来自解析的6 ]。从对映纯二烯（1ë，3 E，S） - 5的阳离子络合物的两种对映体顺式，顺式- 7成为通过相应的中性三羰基的非对映混合物的色谱拆分容易获得（η 4 -二烯）合铁（0）配合物6 [（1- [R，5小号） - 6 ψ-内切- 6和（1级小号，5小号） - 6 ψ-外型- 6 ; de > 99％，ee> 99％；定量的85％解决之前]。杂原子和碳原子亲核试剂（吗啉，甲硅烷基烯醇醚8和甲硅烷基烯酮缩醛9）的亲核加成到外消旋复合物syn，syn-（1

  DOI：

  10.1016/s0022-328x(96)06850-7

文献信息

• An observation of diastereoface selectivity in thermal reactions between δ-alkoxyallylstannanes and aldehydes
  作者：Simon V Mortlock、Eric J Thomas

  DOI：10.1016/s0040-4039(00)87912-5

  日期：1988.1

  The δ-alkoxyallylstannanes (4) and (5) react stereoselectively on heating with -nitrobenzaldehyde to provide the homoallylic alcohols (14) - (17), with (14): (15) = 82: 18; (16): (17) = 73: 27.

  δ-烷氧基烯丙基锡烷（4）和（5）在加热下与-硝基苯甲醛进行立体选择反应，得到均烯丙基醇（14）-（17），其中（14）：（ 15）= 82：18; （16）：( 17）＝ 73：27。
• Intramolecular nitrile oxide cycloaddition on chiral olefins: a stereocontrolled approach to β-ketol precursors
  作者：Rita Annunziata、Mauro Cinquini、Franco Cozzi、Giulio Dondio、Laura Raimondi

  DOI：10.1016/s0040-4020(01)86823-x

  日期：——

  The intramolecular nitrile oxide cycloaddition reaction on chiral (E) and (Z) olefins featuring a sulphur atom along the carbon chain connecting dipole and dipolarophile occurs with poor to excellent anti stereoselectivity, which is mainly affected by the substitutents at the allylic stereocenter. The possibility of converting the cycloadducts into stereoisomerically pure β-ketols has been established

  沿连接偶极子和亲偶极子的碳链上具有硫原子的手性（E）和（Z）烯烃的分子内腈氧化物环加成反应发生时，其抗立体选择性差到极佳，这主要受烯丙基立体中心的取代基影响。在一种情况下，已经确定了将环加合物转化为立体异构纯的β-酮醇的可能性。
• [EN] ENANTIOSELECTIVE SYNTHESIS OF ?-AMINO-a,ß-UNSATURATED CARBOXYLIC ACID DERIVATIVES<br/>[FR] SYNTHÈSE ÉNANTIOSÉLECTIVE DE DÉRIVÉS D'ACIDES CARBOXYLIQUES G-AMINO-?,?-INSATURÉS
  申请人：NOVARTIS AG

  公开号：WO2010055162A1

  公开（公告）日：2010-05-20

  Provided is an enantioselective, palladium-catalyzed method for the preparation of γ-amino-α,β-unsaturated carboxylic acid derivatives having the formulas II, III, IV and VIII.

  提供了一种手性选择性的钯催化方法，用于制备具有 II、III、IV 和 VIII 公式的γ-氨基-α，β-不饱和羧酸衍生物。
• Diastereoselectivity of the thio-Claisen rearrangement of acyclic precursors bearing a chiral centre adjacent to carbon 6
  作者：Stéphane Désert、Patrick Metzner

  DOI：10.1016/s0040-4020(01)88337-x

  日期：1992.11

  allylic alcohols have been prepared and submitted to a Mitsunobu reaction with dithioacetic acid. Allyl dithioesters were deprotonated by LDA at −30°C and resulting enethiolates were quenched with iodomethane to afford quantitatively S-allyl ketenedithioacetals. These precursors undergo a thio-Claisen rearrangement under smooth conditions: room temperature or heating at 101°C. The diastereoselectivity of

  已经制备了许多手性烯丙基醇，并使其与二硫代乙酸进行Mitsunobu反应。在-30℃下通过LDA使烯丙基二硫代酸酯去质子化，并将所得的烯硫醇化物用碘甲烷淬灭，以定量地提供S-烯丙基烯酮二硫缩醛。这些前体在光滑条件下进行硫代克莱森重排：室温或101°C加热。关于立体发生中心的两个取代基的性质，研究了这种σ位移的非对映选择性。对于甲基和叔丁基，观察到75:25的比例，并通过空间位阻来解释。对于各种烷氧基，我们观察到非常适度的选择性，有利于顺式非对映异构体。
• Regio- and Stereoselective Synthesis of Alkyl Allylic Ethers via Gold(I)-Catalyzed Intermolecular Hydroalkoxylation of Allenes with Alcohols
  作者：Zhibin Zhang、Ross A. Widenhoefer

  DOI：10.1021/ol800646h

  日期：2008.5.1

  carbene complex and AgOTf at room temperature for 1 h led to isolation of (E)-(3-phenethoxy-1-butenyl)benzene in 96% yield as a single regio- and stereoisomer. Gold(I)-catalyzed intermolecular allene hydroalkoxylation was effective for monosubsituted, 1,1- and 1,3-disubstituted, trisubstituted, and tetrasubstituted allenes and for a range of primary and secondary alcohols, methanol, phenol, and propionic

  金（I）N-杂环卡宾配合物与AgOTf的1：1混合物在室温下催化1-苯基-1,2-丁二烯与2-苯基-1-乙醇的反应1小时，导致分离出（ E）-（3-苯乙氧基-1-丁烯基）苯作为单一的区域和立体异构体，产率为96％。金（I）催化的分子间烯丙基氢烷氧基化对于单取代的1，1-和1，3-二取代的，三取代的和四取代的烯丙基以及一系列伯和仲醇，甲醇，苯酚和丙酸是有效的。