(S)-(-)-1,1,2-三苯基-1,2-丁二醇2-醋酸酯 | 95061-51-1

• 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: (S)-(-)-1,1,2-三苯基-1,2-丁二醇2-醋酸酯
• 中文别名: 醋酸(S)-(-)-2-羟基-1,2,2-三苯乙酯；(S)-(-)-2-羟基-1,2,2-三苯基乙酸乙酯
• 英文名称: (S)-2-acetoxy-1,1,2-triphenylethanol
• 英文别名: (1s)-2-Hydroxy-1,2,2-triphenylethyl acetate；[(1S)-2-hydroxy-1,2,2-triphenylethyl] acetate
• CAS: 95061-51-1
• 化学式: C₂₂H₂₀O₃
• mdl: MFCD00066241
• 分子量: 332.399
• InChiKey: GXLZCXZLVDUDHP-NRFANRHFSA-N

物化性质

• 熔点：
  246-249 °C
• 沸点：
  429.52°C (rough estimate)
• 密度：
  1.180
• 稳定性/保质期：
  在常温常压下稳定，避免与不相容材料接触。应避免与强氧化剂反应。

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.136
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2915390090
• 安全说明：
  S24/25
• WGK Germany：
  3
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  密封保存，应储存在阴凉干燥的仓库中。

SDS

Name:	(S)-(-)-2-Hydroxy-1 2 2-triphenylethyl acetate 99% Material Safety Data Sheet
Synonym:	(S)-1,1,2-Triphenyl-1,2-ethanediol 2-acetate
CAS:	95061-51-1

Section 1 - Chemical Product MSDS Name:(S)-(-)-2-Hydroxy-1 2 2-triphenylethyl acetate 99% Material Safety Data Sheet
Synonym:(S)-1,1,2-Triphenyl-1,2-ethanediol 2-acetate

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
95061-51-1	(S)-(-)-2-Hydroxy-1,2,2-triphenylethyl	99%	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: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. 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 cool, dry place. Store in a tightly closed container.

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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# 95061-51-1: 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
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 248 - 252 deg C
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: C22H20O3
Molecular Weight: 332.1382

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 95061-51-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(S)-(-)-2-Hydroxy-1,2,2-triphenylethyl acetate - 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# 95061-51-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 95061-51-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 95061-51-1 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：

  (S)-(-)-1,1,2-三苯基-1,2-丁二醇2-醋酸酯 在 咪唑 、 magnesium bromide 、 lithium diisopropyl amide 作用下， 以 乙腈 为溶剂， 反应 4.67h， 生成 (S)-4-Bromo-3-<(tret-butyldimethylsilyl)oxy>-4-pentenoic acid (S)-1,2,2-triphenyl-2-hydroxyethyl ester
  参考文献：
  名称：

  An efficient asymmetric synthesis of 1.alpha.,25-(OH)2 vitamin D3 A-ring synthon

  摘要：

  Chiral synthesis of the A-ring synthon 3 of 1alpha,25-dihydroxyvitamin D3 (1a) based on palladium-catalyzed cyclization of 8-bromo-2,8-nonadienoates is described. Reaction of (E)-4b and (Z)-4d in the presence of Pd(OAc)2, PPh3, and K2CO3 gave (E)-3b and (Z)-3d, respectively. Optically active 4d was prepared from 24 by asymmetric aldol reaction using 31, which was cyclized to 3d. With further reactions, 1alpha,25-dihydroxyvitamin D3 (1a) was obtained.

  DOI：

  10.1021/jo00061a028
• 作为产物：
  描述：

  L-扁桃酸甲酯 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 (S)-(-)-1,1,2-三苯基-1,2-丁二醇2-醋酸酯
  参考文献：
  名称：

  (-)-Disorazole C1的全合成

  摘要：

  Disorazoles 代表了一类从粘细菌中分离出来的强效抗微管蛋白天然产物。在此，我们描述了具有高立体选择性的 (-)-二恶唑 C 1的可扩展且稳健的合成，其特点是反应条件非常简单，可用于生产大量这种显着的生物活性化合物。

  DOI：

  10.1021/acs.orglett.1c01123
• 作为试剂：
  描述：

  3-(2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl)prop-2-enal 、 醋酸叔丁酯 在 正丁基锂 、 (S)-(-)-1,1,2-三苯基-1,2-丁二醇2-醋酸酯 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.5h， 以6.15 g的产率得到(5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3-oxo-5-hydroxy-6-heptenoic acid tert-butyl ester
  参考文献：
  名称：

  匹伐他汀钙中间体的一种非对映异构体及其制备方法

  摘要：

  本发明属于药物化学领域，本发明涉及一种匹伐他汀钙中间体非对映异构体(3S,5S型异构体)即(3S,5S,6E)‑7‑[2‑环丙基‑4‑(4‑氟苯基)‑3‑喹啉基]‑3,5‑二羟基‑3,5‑O‑亚异丙基‑6‑庚烯酸叔丁酯。本发明还涉及匹伐他汀钙中间体非对映异构体(3S,5S型异构体)的制备方法，及其用于检测匹伐他汀钙中间体纯度或光学异构体含量以及匹伐他汀钙生产或制备过程中中间体质量控制的用途。

  公开号：

  CN109384772A

文献信息

• PROCESS FOR THE PREPARATION OF ATORVASTATIN AND INTERMEDIATES
  申请人：Wang Fan

  公开号：US20060194867A1

  公开（公告）日：2006-08-31

  A process is provided for preparing (R)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-5-hydroxy-3-oxo-1-heptanoic acid, R-substituted ester 9 comprising: (a) reacting the aldehyde 1 with the enolate form of (S)-2-hydroxy-1,2,2-triphenylethyl acetate substituent in a chelating co-solvent; (b) hydrolysis of (R,S)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-3-hydroxy-1-pentanoic acid, (S)-2-hydroxy-1,2,2-triphenylethyl ester (2a and 2b) using a base, preferably an alkali metal base, preferably in a solvent to form the carboxylic acid 7; (c) treating the acid 7 with a chiral base to form a salt and purifying the salt to obtain enantiomerically enriched (R)-7 chiral base salt; (d) alkylation of the (R)-7 chiral base salt or the free base derived from (R)-7, forming (R)-5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-5-hydroxy-3-oxo-1-heptanoic acid, R-substituted ester 9 and atorvastatin calcium 6, wherein R is a C1 to C6 alkyl, C6 to C9 aryl or C7 to C10 aralkyl.

  提供了一种制备(R)-5-[2-(4-氟苯基)-5-(1-甲基乙基)-3-苯基-4-[(苯基氨基)羰基]-1H-吡咯-1-基]-5-羟基-3-氧代-1-庚酸，R-取代酯9的过程，包括：(a)将醛1与(S)-2-羟基-1,2,2-三苯乙基醋酸酯取代物的烯醇形式在螯合共溶剂中反应；(b)水解(R,S)-5-[2-(4-氟苯基)-5-(1-甲基乙基)-3-苯基-4-[(苯基氨基)羰基]-1H-吡咯-1-基]-3-羟基-1-戊酸，(S)-2-羟基-1,2,2-三苯乙基酯(2a和2b)使用碱，优选为碱金属碱，优选在溶剂中形成羧酸7；(c)用手性碱处理酸7以形成盐并纯化盐以获得对映富集的(R)-7手性碱盐；(d)烷基化(R)-7手性碱盐或由(R)-7衍生的游离碱，形成(R)-5-[2-(4-氟苯基)-5-(1-甲基乙基)-3-苯基-4-[(苯基氨基)羰基]-1H-吡咯-1-基]-5-羟基-3-氧代-1-庚酸，R-取代酯9和阿托伐他汀钙6，其中R是C1到C6烷基，C6到C9芳基或C7到C10芳基甲基。
• Simple Three-Step Synthesis of (<i>R</i>)- and (<i>S</i>)-4-Amino-3-hydroxybutanoic Acid (GABOB) by Stereoselective Aldol Addition
  作者：Manfred Braun、Delia Waldmüller

  DOI：10.1055/s-1989-27410

  日期：——

  A simple synthesis of both (R)- and (S)-GABOB (5) is reported. In the key step, doubly deprotonated (R)- or (S)-2-Hydroxy-1,2,2-triphenylethyl acetate (HYTRA) (1) is added to Cbz-protected glycinal (2).

  报道了一种简单的同时合成(R)-和(S)-GABOB (5)的方法。在关键步骤中，双去质子的(R)-或(S)-2-羟基-1,2,2-三苯基乙基乙酸酯(HYTRA) (1) 被添加到苄氧羰基保护的甘氨酸醛 (2)中。
• Synthetic studies of the detoxin complex. I. total synthesis of (-) detoxinine
  作者：W.R. Ewing、B.D. Harris、K.L. Bhat、M.M. Joullie'

  DOI：10.1016/0040-4020(86)80005-9

  日期：1986.1

  A total synthesis of (-) detoxinine (1), the parent amino acid of the detoxin complex is reported. Two different routes to key intermediate 8a were developed: one from an acyclic precursor and the other from L-proline. The elaboration of 8a to 1 employed a stereoselective aldol condensation.

  据报道，共合成了排毒复合物的母体氨基酸（-）排毒素（1）。已开发出两种通往关键中间体8a的不同途径：一种途径来自无环前体，另一种途径来自L-脯氨酸。对8a至1的修饰采用了立体选择性醛醇缩合。
• Synthesis of<i>N</i>-Boc-Statine and<i>epi</i>-Statine
  作者：Peter G. M. Wuts、Sterling R. Putt

  DOI：10.1055/s-1989-27442

  日期：——

  The amino acid statine and its C-3 epimer have been prepared stereoselectively as their N-tert-butoxycarbonyl (N-Boc) derivatives 8 and 9 from (S)-Boc-leucinal (1), and (S)-(2) and (R)-1,1,2-triphenyl-2-acetoxythanol (3), respectively.

  氨基酸statine及其C-3表异构体已通过立体选择性的方法，从(S)-Boc-leucinal (1)以及(S)-(2)和(R)-1,1,2-三苯基-2-乙酰氧基乙醇(3)分别制备为其N-叔丁氧羰基(N-Boc)衍生物8和9。
• Synthesis of Epothilones: Stereoselective Routes to Epothilone B
  作者：Dieter Schinzer、Armin Bauer、Jennifer Schieber

  DOI：10.1055/s-1998-1794

  日期：1998.8

  In connection with our studies of the total syntheses of epothilones we report our efforts on the syntheses of epothilone B using a macro-lactonization and a metathesis approach. Key reaction for the solution of the acyclic stereoselection is a stereoselective aldol reaction.

  在我们的埃博霉素全合成研究中，我们报道了采用大环内酯化和复分解方法合成埃博霉素B的努力。解决非环状立体选择性的关键反应是一项立体选择性的羟醛反应。