(R)-2-羟基-3-丁烯-1-对甲苯磺酸 | 138249-07-7

• 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: (R)-2-羟基-3-丁烯-1-对甲苯磺酸
• 中文别名: (R)-1-甲苯磺酰氧基-3-丁烯-2-醇
• 英文名称: (R)-1-tosyloxy-3-buten-2-ol
• 英文别名: (S)-1-(tosyloxy)-2-hydroxybut-3-ene；2(R)-hydroxy-3-buten-1-yl tosylate；(R)-2-hydroxylbut-3-enyl 4-methylbenzenesulfonate；(R)-2-hydroxybut-3-enyl tosylate；2-hydroxy-(2R)-3-butenyl-4-methyl-1-benzenesulfonate；(2R)-1-en-2-hydroxyl-3-O-tosyl-sn-glycerol；(R)-3-Butene-1,2-diol-1-(p-toluenesulfonate)；[(2R)-2-hydroxybut-3-enyl] 4-methylbenzenesulfonate
• CAS: 138249-07-7
• 化学式: C₁₁H₁₄O₄S
• 分子量: 242.296
• InChiKey: YQSCDBZHHLIPOI-SNVBAGLBSA-N

物化性质

• 熔点：
  58-63 °C
• 沸点：
  355.12°C (rough estimate)
• 密度：
  1.3329 (rough estimate)
• 稳定性/保质期：
  遵循规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24,S25,S26
• 危险类别码：
  R36/37/38
• 储存条件：
  存储于2-8°C阴凉干燥处。

SDS

Name:	(R)-2-Hydroxy-3-buten-1-yl p-tosylate 99% (gc) Material Safety Data Sheet
Synonym:
CAS:	138249-07-7

Section 1 - Chemical Product MSDS Name:(R)-2-Hydroxy-3-buten-1-yl p-tosylate 99% (gc) Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
138249-07-7	(R)-2-hydroxy-3-buten-1-yl p-tosylate	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. If heated, dust or fume 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:
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.
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. Water runoff can cause environmental damage. Dike and collect water used to fight fire. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Flammable solid. May burn rapidly with flare burning effect. May be ignited by friction, heat, sparks, or flame. May re-ignite after fire is extinguished.
Extinguishing Media:
Use agent most appropriate to extinguish fire. For large fires, use water spray, fog or regular foam. For small fires, use dry chemical, carbon dioxide, sand, earth, water spray or regular foam. Cool containers with flooding quantities of water until well after fire is out.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Avoid runoff into storm sewers and ditches which lead to waterways.
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. 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. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep away from heat, sparks, and flame. Keep away from sources of ignition. 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. Keep refrigerated. (Store below 4C/39F.)

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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# 138249-07-7: 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: Solid
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 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: C11H14O4S
Molecular Weight: 242.30

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, ignition sources, dust generation, excess heat, strong oxidants.
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# 138249-07-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(R)-2-hydroxy-3-buten-1-yl p-tosylate (gc) - 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# 138249-07-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 138249-07-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 138249-07-7 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：

  (R)-2-羟基-3-丁烯-1-对甲苯磺酸 在 sodium hydroxide 作用下， 以 氘代甲醇 、 重水 为溶剂， 生成
  参考文献：
  名称：

  Identification of Novel Metabolites of Butadiene Monoepoxide in Rats and Mice

  摘要：

  Differences in the metabolism of 1,3-butadiene (Bd) in rats and mice may account for the observed species difference in carcinogenicity. Previous studies of the metabolic fate of Ed have identified epoxide formation as a key metabolic transformation which gives 1,2-epoxy-3-butene (BMO), although some evidence of aldehyde metabolites is reported. In this study, male Sprague-Dawley rats and male B6C3F1 mice received single doses of [4-C-14]BMO at 1, 5, 20, and 50 mg/kg of body weight (0.014, 0.071, 0.286, and 0.714 mmol/kg of body weight). Analysis of urinary metabolites indicated that both species preferentially metabolize BMO by direct reaction with GSH when given by ip administration. The excretion of (R)-2-(N-acetyl-L-cystein-S-yl)-1-hydroxybut-3-ene (IIa), 1-(N-acetyl-L-cystein-S-yl)-2-(S)-hydroxybut-3-ene (IIb), 1-(N-acetyl-L-cystein-S-yl)-2-(R)-hydroxybut-3-ene (IIc), and (S)-2-(N-acetyl-L-cystein-S-yl)- 1-hydroxybut-3-ene (IId) accounted for 48-64% of urinary radioactivity in rats and 46-54% in mice. The metabolites originating from the R-stereoisomer of BMO (IIc and IId) predominated over those arising from the S-stereoisomer (IIa and IIb) in both species. IIc was formed preferentially in mice and IId in rats. The corresponding mercaptoacetic acids, S-(1-hydroxybut-3-en-2-yl)mercaptoacetic acid (IIf) and S-(2-hydroxybut-3-en-1-yl)mercaptoacetic acid (IIg), were identified only in mouse urine (ca. 20% of the recovered radioactivity,, 4-(N-Acetyl-L-cystein-S-yl)- 1,2-dihydroxybutane (Ia), a metabolite derived from hydrolysis of BMO, accounted for 10-17% of the radioactivity in rat and 6-10% in mouse urine. 4-(N-Acetyl-L-cystein-S-yl)-2-hydroxybutanoic acid (1b), 3-(N-acetyl-L-cystein-S-yl)propan-1-ol (Ic), and 3-(N-acetyl-L-cystein-S-yl)propanoic acid (Id:). also derived from the hydrolysis of RR IO, were only present in the rat. Metabolites of 1,2,3,4-diepoxybutane (DEB) were not detected after administration of BMO in rat or mouse urine. This study showed both quantitative and qualitative differences in the metabolism of BMO with varying doses and between species. The data aid in the safety evaluation of Ed and contribute to the interpretation of mathematical models developed for quantitative risk assessment and extrapolation of animals to humans.

  DOI：

  10.1021/tx970175v
• 作为产物：
  描述：

  (±)-2-acetoxybut-3-enyl tosylate 在 phosphate buffer 、 Pseudomonas Amano PS lipase 作用下， 反应 2.75h， 以41%的产率得到(R)-2-羟基-3-丁烯-1-对甲苯磺酸
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiomerically pure alkene 1,2-diols and glycosides thereof

  摘要：

  The kinetic resolution of racemic 2-O-acylated 3-butene-1,2-diol and 1-O-acylated 3-butene-1,2-diol derivatives by enzymatic saponification and enzymatic esterification, respectively, is investigated with several lipases and esterases. The resulting partially blocked enantiomers are glycosylated with glycosyl halides and trichloroacetimidates, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00051-2

文献信息

• Enzyme-mediated enantioselective hydrolysis of 1,2-diol monotosylate derivatives bearing an unsaturated substituent
  作者：K. Matsumoto、K. Oohana、M. Hashimoto、K. Usuda、T. Shimoda、H. Ohshima、Y. Suzuki、T. Togawa

  DOI：10.1016/j.tet.2018.05.087

  日期：2018.7

  We have succeeded in the easy preparation of optically active 1,2-diol monotosylates bearing an unsaturated substituent via enzymatic hydrolysis. Lipase PS quickly catalyzes the hydrolyses of 2-acetoxybut-3-enyl tosylate, which has a double bond, and 2-acetoxybut-3-ynyl tosylate, which has a triple bond, with excellent enantioselectivity to afford the corresponding optically active compounds. The reaction

  我们已经成功地通过酶水解容易地制备了带有不饱和取代基的光学活性的1,2-二醇单甲苯磺酸酯。脂肪酶PS快速催化具有双键的2-乙酰氧基丁-3-烯基甲苯磺酸酯和具有三键的2-乙酰氧基丁-3-炔基甲苯磺酸酯的水解，具有出色的对映选择性，可提供相应的旋光化合物。该反应也适用于在末端具有双键的较长链的乙酸酯。为了证明该方法的适用性，已从外消旋的2-乙酰氧基戊-4-烯基甲苯磺酸酯中分几步合成了对映体纯的（R）-马苏阿内酯，一种天然椰子香精。此外，该酶可以识别烯烃的立体化学，而（Z）-烯基结构比（E）-异构体更适合于对映选择性水解。
• Synthesis and Characterization of Oligodeoxynucleotides Containing an N1 β-Hydroxyalkyl Adduct of 2‘-Deoxyinosine
  作者：Agnieszka Kowalczyk、Constance M. Harris、Thomas M. Harris

  DOI：10.1021/tx010025r

  日期：2001.6.1

  has been developed for synthesis of oligonucleotides containing N1-adducted 2'-deoxyinosines. The 2'-deoxyinosine adduct of 3,4-epoxy-1-butene was prepared from (+/-)-4-acetoxy-3-bromo-1-butene and tetraisopropyldisiloxanediyl-protected 2'-deoxyinosine with base. The 2'-deoxyinosine derivative was then incorporated into the oligodeoxynucleotide sequence 5'-d(CGGACXAGAAG)-3' (X = N1-(1-hydroxy-3-bu

  由简单的环氧化物在腺嘌呤核苷的N1位反应产生的羟乙基加合物可以脱氨基生成肌苷类似物，如果在DNA中形成，则被怀疑具有高度致突变性。已经开发出一种用于合成包含N1加成的2'-脱氧肌苷的寡核苷酸的方法。3，4-环氧-1-丁烯的2'-脱氧肌苷加合物由（+/-）-4-乙酰氧基-3-溴-1-丁烯和四异丙基二硅氧烷二基保护的2'-脱氧肌苷与碱制备。然后将2′-脱氧肌苷衍生物掺入寡脱氧核苷酸序列5′-d（CGGACXAGAAG）-3′（X ＝ N1-（1-羟基-3-丁烯-2-基）-2′-脱氧肌苷）。
• Application to the Synthesis of Enantiopure Phosphonates Analogous to Triglycerides: A New Class of Inhibitors of Lipases
  作者：Frank Marguet、Jean-François Cavalier、Robert Verger、Gérard Buono

  DOI：10.1002/(sici)1099-0690(199907)1999:7<1671::aid-ejoc1671>3.0.co;2-z

  日期：1999.7

  3-O-didecanoylglycerol compounds were prepared – starting from a C-4 chiral synthon, 3-buten-1,2-diol – and treated with n-pentylphosphonic dichloride and p-nitrophenol to afford the corresponding diastereomeric phosphonates, which were acylglycerol analogs. Subsequent separation of each of the phosphonate diastereomers A/B or ent-A/ent-B, performed by HPLC, led to four enantiopure stereoisomers that will be

  膦酸酯化合物通过与催化丝氨酸形成共价键来模拟在天然底物的酶促羧酸酯水解过程中发生的第一个过渡态。然而，迄今为止，用于抑制研究的有机磷化合物或多或少类似于天然甘油三酯底物。为了阐明脂肪酶的界面活化和作用机制，需要制备特异性抑制剂。为了实现这一目标，从 C-4 手性合成子、3-丁烯-1,2-二醇开始，制备了对映体纯的 sn-1,2- 和 sn-2,3-O-二癸酰基甘油化合物，并用 n -戊基膦酰二氯和对硝基苯酚得到相应的非对映膦酸酯，它们是酰基甘油类似物。随后分离每种膦酸酯非对映异构体 A/B 或 ent-A/ent-B，
• Sub-stoichiometric reductive etherification of carbohydrate substrates and one-pot protecting group manipulation
  作者：Chiao Wen Chen、Ching Chi Wang、Xin Ru Li、Henryk Witek、Kwok-Kong Tony Mong

  DOI：10.1039/d0ob00252f

  日期：——

  its application for one-pot preparation of glycosyl building blocks. The reported procedure features the use of polymethylhydrosiloxane (PMHS) as a sub-stoichiometric reducing agent, which prevents the transilylation side reaction and improves the efficiency of the reductive etherification method. Application of the PMHS reductive etherification procedure for one-pot protecting group manipulation are

  在这项研究中，我们报告了一种新的还原性醚化程序，用于保护碳水化合物底物及其在单罐糖基结构单元制备中的应用。所报道的方法的特征在于使用聚甲基氢硅氧烷（PMHS）作为亚化学计量的还原剂，可防止反硅烷化副反应并提高还原醚化方法的效率。描述了PMHS还原醚化方法在一锅保护基操纵中的应用。
• Expedient Synthesis of Epigoitrin From L-Ascorbic Acid
  作者：Jing-Jing Yang、Jian-Zhong Wu、Chunhua Qiao

  DOI：10.1080/00397911.2013.850092

  日期：2014.5.3

  Extensive biological exploration of epigoitrin was constrained by the limited natural source. This article describes our continued effort toward chemical preparation of epigoitrin from the readily available L-ascorbic acid. Our new developed synthetic route is composed of nine steps, with an overall yield of 17%. GRAPHICAL ABSTRACT

  摘要 Epigoitrin是重要的中草药板蓝根的主要生物活性成分。已报道的表依序的药理作用包括抗病毒、抗癌和抗甲状腺活性。由于天然来源有限，对表依依止的广泛生物学探索受到限制。这篇文章描述了我们从容易获得的 L-抗坏血酸化学制备表依依止的持续努力。我们新开发的合成路线由九个步骤组成，总收率为17%。图形概要