L-酒石酸二丁酯 | 87-92-3

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: L-酒石酸二丁酯
• 中文别名: L-(+)-酒石酸二丁酯
• 英文名称: (+)-(2R,3R)-dibutyl tartrate
• 英文别名: L(+) tartaric acid dibutyl ester；dibutyl-(l)-(+)-tartrate；(R,R)-dibutyl tartrate；di-n-butyl-L-tartrate；dibutyl L-tartrate；dibutyl-L-tartrate；Dibutyl tartrate；dibutyl (2R,3R)-2,3-dihydroxybutanedioate
• CAS: 87-92-3
• 化学式: C₁₂H₂₂O₆
• 分子量: 262.303
• InChiKey: PCYQQSKDZQTOQG-NXEZZACHSA-N

物化性质

• 熔点：
  20-22 °C
• 沸点：
  182 °C (11 mmHg)
• 密度：
  1.09
• 闪点：
  167 °C
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）
• 稳定性/保质期：
  与强氧化剂反应。它是可燃性物质，使用时需远离火源。在常温下，特别是在有水存在的条件下，它的化学性质不够稳定，会逐渐发生水解，释放出酒石酸。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2918130000
• 储存条件：
  密封保存，应存放在阴凉干燥处。

SDS

Name:	Dibutyl L-Tartrate Material Safety Data Sheet
Synonym:	None
CAS:	87-92-3

Section 1 - Chemical Product MSDS Name:Dibutyl L-Tartrate Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
87-92-3	N-Dibutyl Tartrate	ca 100	201-784-9

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. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
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.
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:

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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. Use water spray to keep fire-exposed containers cool. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Containers may explode when heated.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Cool containers with flooding quantities of water until well after fire is out. 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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Remove all sources of ignition. 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:
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# 87-92-3: 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:
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: 167 deg C ( 332.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.0900g/cm3
Molecular Formula: C12H22O6
Molecular Weight: 262.29

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 87-92-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N-Dibutyl Tartrate - 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.
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# 87-92-3: No information available.
Canada
CAS# 87-92-3 is listed on Canada's NDSL List.
CAS# 87-92-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 87-92-3 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

概述

由于手性化合物尤其是手性药物的两个对映体具有不同的化学性质和生理活性，近年来对手性分离的关注度日益增加。L-酒石酸二丁酯不仅可用于手性化合物的拆分，还可作为硝酸纤维素、酯酸纤维素的增塑剂。特别地，在与磷酸三甲苯酯混合使用时，可以在硝酸纤维素中生成稳定的耐水涂膜；在酯酸纤维素中与苄醇混合使用时，同样可以形成类似的涂膜。

应急处理方法

如果吸入L-酒石酸二丁酯，请立即将患者移至新鲜空气处；若皮肤接触到该物质，请脱去污染衣物，并用肥皂水和清水彻底清洗受污染的皮肤，如有不适，请及时就医；如眼睛接触，则需分开眼睑，使用流动清水或生理盐水冲洗，并立即寻求医疗帮助；如果误食，应立刻漱口并禁止催吐，随后尽快就医。

应用

L-酒石酸二丁酯可用作硝酸纤维素和酯酸纤维素的增塑剂。尤其在与磷酸三甲苯酯混合使用时，在硝酸纤维素中可以生成稳定的耐水涂膜；而在酯酸纤维素中与苄醇结合，则同样能够形成类似的效果。此外，它还被用于制备提高复方丁公藤注射液安全性的药物组合物。

反应信息

• 作为反应物：
  描述：

  L-酒石酸二丁酯 在 四氢呋喃 、 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 L-苏丁醇
  参考文献：
  名称：

  立体化学方面-I：某些二醇的性质和反应

  摘要：

  分子内氢键的如通过羟基拉伸区域红外光谱，在某些邻二醇确定的范围内，环己烷，环戊烷，四氢吡喃和四氢呋喃和相关化合物提供了用于不同的构象的稳定性的证据。在某些化合物中，这些稳定性可能会受到取代基羟基与环氧之间氢键的影响。对于四氢吡喃二醇，通过[ M ] D值提供了其他证据。这些环状体系的邻位二醇与二醇拆分剂的反应速率及其在碱性硼酸盐缓冲液中的区带电泳迁移率受环氧的影响。

  DOI：

  10.1016/0040-4020(58)80056-3
• 作为产物：
  描述：

  dibenzyl (2R,3R)-2,3-dihydroxybutanedioate 、 正丁醇 以 various solvent(s) 为溶剂， 反应 24.0h， 以86.2%的产率得到L-酒石酸二丁酯
  参考文献：
  名称：

  A convenient method for enzymatic benzyl-alkyl transesterification under mild neutral conditions

  摘要：

  Lipases from Candida cylindracea and from Pseudomonas fluorescens efficiently catalyse the benzyl to alkyl transesterification in organic solvents under mild conditions in nearly quantitative yields.

  DOI：

  10.1016/s0040-4020(01)89450-3
• 作为试剂：
  描述：

  3β-(t-butyl)dimethyl-siloxy-androst-5-ene-17β-carboxaldehyde 在 palladium on barium sulfate 喹啉 、 正丁基锂 、 L-酒石酸二丁酯 、 氢气 、 diethylzinc 、 二异丁基氢化铝 、 三苯基膦 、 锌 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Complexation of Vinylcyclopropanes with Zirconocene−1-butene Complex:  Application to the Stereocontrolled Synthesis of Steroidal Side Chains

  摘要：

  Reactions of vinylcyclopropane derivatives with a zirconocene-1-butene complex (''Cp2Zr'') caused regioselective cleavage of the cyclopropyl bond to give eta(3) pi-allylic and/or eta(1) sigma-allylic complexes. The regioselectivity of the bond cleavage and the formation of a eta(3) pi-allylic or eta(1) sigma-allylic complex depend on the bulkiness of the substituents on the cyclopropyl group and the presence of leaving functionality. A catalytic use of ''Cp2Zr'' in the presence of excess Grignard reagent also caused a ring opening of the vinylcyclopropane derivatives with the same sense of regiochemical selectivity. The reaction of the thermally equilibrated ''Cp2Zr''-propenylcyclopropane complex with acetone indicated the possibility for the synthesis of the steroidal side chain in either natural or unnatural forms. The synthetic utility of the present ''Cp2Zr''-vinylcyclopropane chemistry was ascertained by the stereocontrolled preparation of the C-20, C-24 dimethylated steroidal side chain which is identical to the active metabolite of vitamin D-2.

  DOI：

  10.1021/jo962064r

文献信息

• Imidazolium-based chiral ionic liquids: synthesis and application
  作者：Yumiko Suzuki、Junichiro Wakatsuki、Mariko Tsubaki、Masayuki Sato

  DOI：10.1016/j.tet.2013.09.017

  日期：2013.11

  centers on N-substituents is reported. [(2S,3S)-2,3-Dihydroxybutane-1,4-bis(3-butylimidazolium)]-[bis(trifluoromethanesulfonyl)amide]2 and [(4S,5S)-2-phenyl-1,3-dioxolane-4,5-bis(1-methylimidazolium)]-[bis(trifluoromethanesulfonyl)amide]2 induced enantioselectivity in the Michael addition of malonic esters to chalcones.

  的含有咪唑核和手性中心的手性离子液体的合成ñ -取代基被报告。[（2小号，3小号）-2,3- Dihydroxybutane -1,4-双（3-丁基咪唑）] - [双（三氟甲磺酰）酰胺] 2和[（4-小号，5小号）-2-苯基-1- 1,3-二氧戊环-4,5-二（1-甲基咪唑）] - [双（三氟甲磺酰）酰胺] 2在迈克尔加成丙二酸酯的查耳酮向诱导对映选择性。
• PHOSPHORYLATED POLYOLS, PYROPHOSPHATES, AND DERIVATIVES THEREOF HAVING BIOLOGICAL ACTIVITY
  申请人：NormOxys, Inc.

  公开号：US20140142052A1

  公开（公告）日：2014-05-22

  The present invention provides phosphorylated and pyrophosphate derivatives of polyols, and structural derivatives of these compounds, and provides pharmaceutical compositions comprising the same. The compounds and compositions disclosed herein have various biological activities, including for example, as allosteric effectors of hemoglobin and/or as kinase inhibitors. The present invention further provides methods for therapy in human or mammalian patients, and methods for synthesis of biologically active compounds and their intermediates.

  本发明提供了聚醇的磷酸化和焦磷酸酯衍生物，以及这些化合物的结构衍生物，并提供包含它们的药物组合物。本文披露的化合物和组合物具有各种生物活性，例如作为血红蛋白的变构效应物或激酶抑制剂。本发明还提供了用于人类或哺乳动物患者治疗的方法，以及用于合成生物活性化合物及其中间体的方法。
• [EN] PROCESS FOR PREPARATION OF ACITRETIN<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ACITRÉTINE
  申请人：EMCURE PHARMACEUTICALS LTD

  公开号：WO2016042573A1

  公开（公告）日：2016-03-24

  The present invention provides a process for preparation of (2E,4E,6E,8E)-9-(4-methoxy-2,3,6- trimethyl)phenyl-3,7-dimethyl-nona-2,4,6,8}tetraenoate, an acitretin intermediate of formula (VI) with trans isomer ≥97%, comprising of reacting 3-formyl-crotonic acid butyl ester of formula (V), substantially free of impurities, with 5-(4-methoxy-2,3,6-trimethylphenyl)-3- methyl-penta-2,4-diene-l-triphenyl phosphonium bromide of formula (IV) and isolating resultant compound of formula (VI), treating the filtrate with iodine for isomerization of the undesired cis intermediate and finally obtaining acitretin (I), with desired trans isomer ≥97%.

  本发明提供了一种制备(2E,4E,6E,8E)-9-(4-甲氧基-2,3,6- 三甲基)苯基-3,7-二甲基-壬二烯酸酯，即式（VI）的乙酸类似物的过程，其反应物为式（V）的3-甲酰基-巴比妥酸酯，基本无杂质，与式（IV）的5-(4-甲氧基-2,3,6-三甲基苯基)-3-甲基-戊二烯-1-三苯基磷溴化铵反应，并分离产物（VI）的化合物，用碘处理滤液以异构化不需要的顺式中间体，最终获得乙酸类似物（I），其所需的顺式异构体≥97%。
• Chiral induction in a biomimetic olefin cyclization
  作者：Hideyuki Takenaka、Tomohiro Sato、Mugio Nishizawa

  DOI：10.1016/s0040-4039(00)99667-9

  日期：1989.1

  Chiral induction has been achieved during a biomimetic cyclization of a chiral perillene derivatives in maximum 76% diastereomeric excess. The absolute configuration of the predominant products are established by X-ray diffraction study and chemical transformations.

  在手性紫苏烯衍生物的仿生环化过程中，以最大76％的非对映异构体过量实现了手性诱导。通过X射线衍射研究和化学转化来确定主要产物的绝对构型。
• Asymmetric synthesis of (α-amino)phosphonic acid amphiphiles using chiral P–H spirophosphoranes
  作者：Christophe Déjugnat、Guita Etemad-Moghadam、Isabelle Rico-Lattes

  DOI：10.1039/b304420c

  日期：——

  Chiral P–H spirophosphoranes reacted with long-chain prochiral aldimines and, after selective hydrolysis, afforded (α-amino)phosphonic acid amphiphiles in both enantiopure forms.

  手性 PâH spirophosphoranes 与长链亲手性醛亚胺发生反应，经过选择性水解，得到了两种对映纯形式的（δ-氨基）膦酸两性化合物。

表征谱图