甲基(R)-3-羟基-3-苯基丙酸 | 58692-70-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 中文名称: 甲基(R)-3-羟基-3-苯基丙酸
• 中文别名: (r)-3-羟基-3-苯丙酸甲酯
• 英文名称: methyl (R)-3-hydroxy-3-phenylpropanoate
• 英文别名: (R)-methyl 3-hydroxy-3-phenylpropanoate；methyl 3-hydroxy-3-phenylpropanoate；methyl (3R)-3-hydroxy-3-phenylpropanoate
• CAS: 58692-70-9
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: VZHHCQFCDCJKIX-SECBINFHSA-N

物化性质

• 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)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

SDS

Name:	Methyl (r)-3-hydroxy-3-phenylpropanoate Material Safety Data Sheet
Synonym:	None
CAS:	58692-70-9

Section 1 - Chemical Product MSDS Name:Methyl (r)-3-hydroxy-3-phenylpropanoate Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
58692-70-9	Methyl (r)-3-h	ca.100	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 immediately.
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:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
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:
Antidote: None reported.

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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 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.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. 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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 58692-70-9: 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: Viscous liquid
Color: Clear - colorless
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: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H12O3
Molecular Weight: 180.20

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
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# 58692-70-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl (r)-3-h - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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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.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
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# 58692-70-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 58692-70-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 58692-70-9 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：

  甲基(R)-3-羟基-3-苯基丙酸 在 sodium tetrahydroborate 作用下， 生成 (R)-1-苯基-1,3-丙二醇
  参考文献：
  名称：

  Elucidation of stereospecificity of a selenium-containing hydrogenase from methanococcus vannielii — syntheses of (R)- and (S)-[4-2H1] 3,4-dihydro-7-hydroxy-1-hydroxyethylquinolinone

  摘要：

  DOI：

  10.1016/s0040-4039(01)80815-7
• 作为产物：
  描述：

  (2RS,3RS)-methyl 3-hydroxy-2-(phenylthio)benzenepropanoate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以90%的产率得到甲基(R)-3-羟基-3-苯基丙酸
  参考文献：
  名称：

  Chiral diazaborolidine-mediated enantioselective aldol reactions of phenylthioacetate esters

  摘要：

  Methodology is described for the enantioselective conversion of achiral aldehydes by anti-selective aldol reaction to chiral beta-hydroxy-alpha-phenylthio esters and aldehydes. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00302-6

文献信息

• 2,2‘,5,5‘-Tetramethyl-4,4‘-bis(diphenylphoshino)-3,3‘-bithiophene:  A New, Very Efficient, Easily Accessible, Chiral Biheteroaromatic Ligand for Homogeneous Stereoselective Catalysis
  作者：Tiziana Benincori、Edoardo Cesarotti、Oreste Piccolo、Franco Sannicolò

  DOI：10.1021/jo991533x

  日期：2000.4.1

  C2-symmetry chelating ligand for transition metals, is described, starting from 2,5-dimethylthiophene. The complexes of this electron-rich diphosphine with Ru(II) and Rh(I) were used as catalysts in some homogeneous hydrogenation reactions of prostereogenic carbonyl functions of alpha- and beta-ketoesters, of prostereogenic carbon-carbon double bonds of substituted acrylic acids, and of N-acetylenamino

  对映纯（+）-和（-）-2,2'，5,5'-四甲基-4,4'-双-（二苯基膦基）-3,3'-联噻吩（tetraMe-BITIOP的四步直接合成），描述了一种新的C2对称的过渡金属螯合配体，从2,5-二甲基噻吩开始。这种富电子的二膦与Ru（II）和Rh（I）的配合物在α-和β-酮酸酯的酯基羰基官能团，取代丙烯酸的酯基碳-碳双键的均相加氢反应中用作催化剂和N-乙酰基氨基酸。发现在所有实验中对映体过量都非常好，并且与文献报道的在相同实验条件下进行的相同反应的最佳结果相当，
• Development of an axially chiral sp3P/sp3NH/sp2N-combined linear tridentate ligand—fac-selective formation of Ru(II) complexes and application to ketone hydrogenation
  作者：Tomoya Yamamura、Satoshi Nakane、Yuko Nomura、Shinji Tanaka、Masato Kitamura

  DOI：10.1016/j.tet.2016.02.007

  日期：2016.6

  A newly developed chiral linear tridentate ligand, R-PN(H)N (R=H or Ph), possesses Ph2P and PyCH2NH groups at C(2) and C(2′) positions of the 1,1′-binaphthyl skeleton without or with a C(3)-Ph substituent. The steric effect of C(3)-Ph and the electronic effect of the DMSO co-ligand realize the facial selective generation of fac-RuCl2(Ph-PN(H)N)(dmso) and fac-[Ru(H-PN(H)N)(dmso)3](BF4)2, respectively

  一种新开发的手性线性三齿配体R-PN（H）N（R = H或Ph），在1,1'的C（2）和C（2'）位置具有Ph 2 P和PyCH 2 NH基团-具有或没有C（3）-Ph取代基的-萘基骨架。C（3）-Ph的空间效应和DMSO共配体的电子效应实现了fac -RuCl 2（Ph-PN（H）N）（dmso）和fac- [Ru（H- PN（H）N）（dmso）3 ]（BF 4）2。H-Ru advantageoussp 3 N-H反应位点负责给体-受体双功能催化剂（DACat）和围栏/平面手性环境，均通过以下优点构建：i）sp3 P，sp 3 N和sp 2 N的连接原子具有不同的电子性质；ii）DMSO反式至sp 3 N与Ru强烈配位，并被PyC（6）H = O S氢键固定 iii）单个NH功能简化了DACat反应位点。协同作用已成功地实现了对空间需求的酮的不对称氢化。还研究了R-PN（H）N第一行过渡金属配合物的结构特征。
• A Chiral 6-Membered <i>N</i>-Heterocyclic Carbene Copper(I) Complex That Induces High Stereoselectivity
  作者：Jin Kyoon Park、Hershel H. Lackey、Matthew D. Rexford、Kirill Kovnir、Michael Shatruk、D. Tyler McQuade

  DOI：10.1021/ol1021756

  日期：2010.11.5

  A chiral 6-membered annulated N-heterocyclic (6-NHC) copper complex that catalyzes β-borylations with high yield and enantioselectivity was developed. The chiral 6-NHC copper complex is easy to prepare on the gram scale and is very active, showing 10 000 turnovers at 0.01 mol % of catalyst without significant decrease of enantioselectivity and with useful reaction rates.

  开发了一种手性的六元环状N-杂环（6-NHC）铜络合物，它以高收率和对映选择性催化β-硼化。手性6-NHC铜络合物易于按克规模制备，并且非常活泼，在0.01 mol％的催化剂下显示出1万的周转率，而对映选择性没有显着降低，并且具有有用的反应速率。
• Unprecedented Copper(I) Bifluoride Complexes: Synthesis, Characterization and Reactivity
  作者：Thomas Vergote、Fady Nahra、Alexandre Welle、Michel Luhmer、Johan Wouters、Nathalie Mager、Olivier Riant、Tom Leyssens

  DOI：10.1002/chem.201102655

  日期：2012.1.16

  demonstrated that copper(I) bifluorides are very efficient catalysts, which do not require any additional activating agent. The first Cu‐catalyzed diastereoselective allylation of (R)‐N‐tert‐butanesulfinyl aldimines was also established. The method enables efficient, simple and general synthesis of enantiomerically enriched homoallylic amines at room temperature in high yields.

  成为或不成为双氟化物：已开发出两种合成途径，从而获得了前所未有的N-杂环卡宾铜（I）双氟化物络合物（参见方案）。催化测试表明，氟化氢（I）是非常有效的催化剂，不需要任何其他活化剂。的第一Cu催化的非对映选择性烯丙基化（[R ）- ñ -叔-butanesulfinyl醛亚胺也被建立。该方法能够在室温下以高收率高效，简单和通用地合成对映异构体富集的均烯丙基胺。
• Dimethylzinc-Mediated, Oxidatively Promoted Reformatsky Reaction of Ethyl Iodoacetate with Aldehydes and Ketones
  作者：Pier Giorgio Cozzi、Alessandro Mignogna、Paola Vicennati

  DOI：10.1002/adsc.200700572

  日期：2008.5.5

  A practical and general Reformatsky reaction, promoted by oxidants and mediated by dimethylzinc, is described. The reaction is fast and runs at 0 °C with aldehydes and ketones, under mild reaction conditions. Preliminary results obtained for the enantioselective version show that inexpensive chiral amino alcohols could be used in the challenging formation of enantioenriched quaternary stereogenic centers

  描述了一种由氧化剂促进并由二甲基锌介导的实用且通用的Reformatsky反应。该反应快速，可在温和的反应条件下于0°C与醛和酮一起运行。对映体选择性形式获得的初步结果表明，廉价的手性氨基醇可用于富挑战性地形成对映体富集的季立体异构中心。