(1R,2S)-1,2,3,4-tetrahydronaphthalene-1,2-diol | 57495-92-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (1R,2S)-1,2,3,4-tetrahydronaphthalene-1,2-diol
• 英文别名: (1R,2S)-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene；(-)-(1R,2S)-cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene；1,2-Naphthalenediol, 1,2,3,4-tetrahydro-, cis-
• CAS: 57495-92-8
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: KMQJJAOZMONGLS-VHSXEESVSA-N

物化性质

• 沸点：
  308.4±42.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)
• 保留指数：
  1515

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

SDS

Name:	(+)-cis-1(r) 2(s)-1 2-dihydroxy-1 2 3 4- tetrahydronaphthalene 98+% Material Safety Data Sheet
Synonym:
CAS:	57495-92-8

Section 1 - Chemical Product MSDS Name:(+)-cis-1(r) 2(s)-1 2-dihydroxy-1 2 3 4- tetrahydronaphthalene 98+% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
57495-92-8	(+)-cis-1(r),2(s)-1,2-dihydroxy-1,2,3,		unlisted

Hazard Symbols: Not available.
Risk Phrases:

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Appearance: white to off-white.
Not available.
Target Organs: None.
Potential Health Effects
The toxicological properties of this material have not been investigated. Use appropriate procedures to prevent opportunities for direct contact with the skin or eyes and to prevent inhalation.

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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 soap and water for at least 15 minutes while removing contaminated clothing and shoes.
Remove contaminated clothing and shoes.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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.

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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.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Keep container closed when not in use.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits +--------------------+-------------------+-------------------+-----------------+ | Chemical Name | ACGIH | NIOSH |OSHA - Final PELs| |--------------------|-------------------|-------------------|-----------------| | (+)-cis-1(r),2(s)-1|none listed |none listed |none listed | | ,2-dihydroxy-1,2,3,| | | | | 4-tetrahydronaphtha| | | | | lene | | | | +--------------------+-------------------+-------------------+-----------------+ OSHA Vacated PELs: (+)-cis-1(r),2(s)-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene: No OSHA Vacated PELs are listed for this chemical.
Personal Protective Equipment Eyes: Wear chemical goggles.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
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 a respirator's use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Not available.
Appearance: white to off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 130.00 - 133.00 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
NFPA Rating: Not published.
Explosion Limits, Lower: Not available.
Upper: Not available.
Decomposition Temperature:
Solubility:
Specific Gravity/Density:
Molecular Formula: C10H12O2
Molecular Weight: 164.20

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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:
Not available.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Not available.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 57495-92-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(+)-cis-1(r),2(s)-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene - Not listed by ACGIH, IARC, NIOSH, NTP, or OSHA.
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Chemical waste generators must determine whether a discarded chemical is classif as a hazardous waste.
US EPA guidelines for the classification determination are listed in 40 CFR Part Additionally, waste generators must consult state and local hazardous waste regu ensure complete and accurate classification.
RCRA P-Series: None listed.
RCRA U-Series: None listed.

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Section 14 - TRANSPORT INFORMATION

CDG/CPL
Not classified as hazardous for supply.
Canadian TDG
No information available.

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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# 57495-92-8: No information available.
United Kingdom Occupational Exposure Limits
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
WHMIS: Not available.
CAS# 57495-92-8 is not listed on Canada's Ingredient Disclosure List.
Exposure Limits
US FEDERAL
TSCA
CAS# 57495-92-8 is not listed on the TSCA inventory.
It is for research and development use only.
Health & Safety Reporting List
None of the chemicals are on the Health & Safety Reporting List.
Chemical Test Rules
None of the chemicals in this product are under a Chemical Test Rule.
Section 12b
None of the chemicals are listed under TSCA Section 12b.
TSCA Significant New Use Rule
None of the chemicals in this material have a SNUR under TSCA.
SARA
Section 302 (RQ)
None of the chemicals in this material have an RQ.
Section 302 (TPQ)
None of the chemicals in this product have a TPQ.
Section 313
No chemicals are reportable under Section 313.
Clean Air Act:
This material does not contain any hazardous air pollutants.
This material does not contain any Class 1 Ozone depletors.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (1R,2S)-1,2,3,4-tetrahydronaphthalene-1,2-diol 在 2-氮杂金刚烷-N-氧自由基 、 碘苯二乙酸 、 四丁基溴化铵 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 生成 3-(2-羧基苯基)丙酸
  参考文献：
  名称：

  硝基氧自由基/ PhI（OAc）2：邻苯二甲酸二酯一锅氧化裂解为（Di）羧酸

  摘要：

  描述了使用AZADO和PhI（OAc）2对邻二醇进行温和且易于使用的一锅氧化裂解为相应的（二）羧酸的方法。1,2-二醇和2,3-二醇以及1,2,3-三醇生成一个或两个碳单元短的羧酸。内部邻位二醇也顺利进行一锅氧化裂解，得到相应的二羧酸。环状邻位二醇被转化为其相应的开放形式二元羧酸。

  DOI：

  10.1021/ol3021435
• 作为产物：
  描述：

  (+)-顺式-1(r),2(s)-1,2-二羟基-1,2-二氢萘 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 (1R,2S)-1,2,3,4-tetrahydronaphthalene-1,2-diol
  参考文献：
  名称：

  阿1个为的对映体过量和绝对构型的确定H-NMR方法顺-dihydrodiol多环芳烃和杂芳烃的代谢物

  摘要：

  恶臭假单胞菌UV4代谢苯并呋喃和2，3-二氢苯并呋喃分别产生顺式-二氢二醇。得自多环芳烃和氮杂芳烃的顺式-二氢二醇的催化加氢反应，然后在顺式-四氢二醇上形成二MTPA酯（同时使用R-和S-MTPA形成）形成了用于测定两种对映体过量的1 H-NMR方法的基础和绝对配置。

  DOI：

  10.1016/s0040-4039(00)91907-5

文献信息

• Highly Enantioselective Iron-Catalyzed <i>cis</i> -Dihydroxylation of Alkenes with Hydrogen Peroxide Oxidant via an Fe^III -OOH Reactive Intermediate
  作者：Chao Zang、Yungen Liu、Zhen-Jiang Xu、Chun-Wai Tse、Xiangguo Guan、Jinhu Wei、Jie-Sheng Huang、Chi-Ming Che

  DOI：10.1002/anie.201603410

  日期：2016.8.22

  catalysts for highly enantioselective asymmetric cis‐dihydroxylation (AD) of alkenes with broad substrate scope remains a challenge. By employing [FeII(L)(OTf)2] (L=N,N′‐dimethyl‐N,N′‐bis(2‐methyl‐8‐quinolyl)‐cyclohexane‐1,2‐diamine) as a catalyst, cis‐diols in up to 99.8 % ee with 85 % isolated yield have been achieved in AD of alkenes with H2O2 as an oxidant and alkenes in a limiting amount. This “[FeII(L)(OTf)2]+H2O2”

  开发具有良好底物范围的烯烃的高对映选择性不对称顺二羟基化（AD）的环境友好型催化剂仍然是一个挑战。通过使用[Fe II（L）（OTf）2 ]（L = N，N'-二甲基-N，N'-双（2-甲基-8-喹啉基）-环己烷-1,2-二胺）作为催化剂，在以H 2 O 2为氧化剂的烯烃和数量有限的烯烃的AD中，已实现了高达99.8％ee的顺式二醇和85％的分离产率。该“ [Fe II（L）（OTf）2 ] + H 2 O 2”方法适用于（E）-烯烃和末端烯烃（24个实例，ee大于80％，最大1 g）。机理研究包括18种O-标记，UV / Vis，EPR，ESI-MS分析和DFT计算，为手性Fe III- OOH活性物种参与两个C-O键的对映选择性形成提供了证据。
• Enantioselective Dihydroxylation of Alkenes Catalyzed by 1,4-Bis(9-<i>O</i> -dihydroquinidinyl)phthalazine-Modified Binaphthyl-Osmium Nanoparticles
  作者：Jie Zhu、Xiao-Tao Sun、Xiao-Dong Wang、Lei Wu

  DOI：10.1002/cctc.201701368

  日期：2018.4.24

  A series of unprecedented binaphthyl–osmium nanoparticles (OsNPs) with chiral modifiers were applied in the heterogeneous asymmetric dihydroxylation of alkenes. A remarkable size effect of the OsNPs, depending on the density of the covalent organic shells, on the reactivity and enantioselectivity of the dihydroxylation reaction was revealed. Successful recycling of the OsNPs was also demonstrated and

  一系列具有手性改性剂的前所未有的联萘-os纳米颗粒（OsNPs）被用于烯烃的异质不对称二羟基化反应中。揭示了取决于共价有机壳的密度，OsNP的显着的尺寸效应，其对二羟基化反应的反应性和对映选择性的影响。还证实了OsNPs的成功回收，并保持了高反应效率和对映选择性。
• OsO4⋅Streptavidin: A Tunable Hybrid Catalyst for the Enantioselective cis-Dihydroxylation of Olefins
  作者：Valentin Köhler、Jincheng Mao、Tillmann Heinisch、Anca Pordea、Alessia Sardo、Yvonne M. Wilson、Livia Knörr、Marc Creus、Jean-Christophe Prost、Tilman Schirmer、Thomas R. Ward

  DOI：10.1002/anie.201103632

  日期：2011.11.11

  Taking control: Selective catalysts for olefin dihydroxylation have been generated by the combination of apo‐streptavidin and OsO4. Site‐directed mutagenesis allows improvement of enantioselectivity and even inversion of enantiopreference in certain cases. Notably allyl phenyl sulfide and cis‐β‐methylstyrene were converted with unprecedented enantiomeric excess.

  采取控制措施：载脂蛋白链霉亲和素和OsO 4的结合产生了用于烯烃二羟基化的选择性催化剂。定点诱变可以提高对映选择性，在某些情况下甚至可以逆转对映选择性。值得注意的是烯丙基苯硫醚和顺-β-甲基苯乙烯的转化对映体过量。
• Reactions of enantiopure cyclic diols with sulfuryl chloride
  作者：Derek R. Boyd、Narain D. Sharma、Magdalena Kaik、Peter B. A. McIntyre、John F. Malone、Paul J. Stevenson

  DOI：10.1039/c4ob00042k

  日期：——

  Monocyclic allylic cis-1,2-diols reacted with sulfuryl chloride at 0 °C in a regio- and stereo-selective manner to give 2-chloro-1-sulfochloridates, which were hydrolysed to yield the corresponding trans-1,2-chlorohydrins. At −78 °C, with very slow addition of sulfuryl chloride, cyclic sulfates were formed in good yields, proved to be very reactive with nucleophiles and rapidly decomposed on attempted

  单环烯丙基顺式-1,2-二醇与硫酰氯在0°C下以区域和立体选择性方式反应，生成2-氯-1-磺酰氯，将其水解生成相应的反式-1,2-氯醇。在-78°C下，以非常缓慢的速度加入硫酰氯，形成的环状硫酸盐收率很高，被证明与亲核试剂具有很高的反应性，并且在试图储存时迅速分解。环状硫酸盐与叠氮化钠的反应产生反式叠氮醇，而没有发生烯丙基重排的迹象。对映体双环顺式-1,2-二醇与硫酰氯反应，仅得到反式-1,2-二氯化物对映异构体，其构型保留在苄基中心，并在非苄基中心反转；提出了一种使观察合理化的机制。
• Enantioselective bacterial biotransformation routes to cis-diol metabolites of monosubstituted benzenes, naphthalene and benzocycloalkenes of either absolute configuration
  作者：Christopher C. R. Allen、Derek R. Boyd、Howard Dalton、Narain D. Sharma、Ian Brannigan、Nuala A. Kerley、Gary N. Sheldrake、Stephen C. Taylor

  DOI：10.1039/c39950000117

  日期：——

  Enzyme-catalysed kinetic resolution and asymmetric dihydroxylation routes to enantiopure cis-diol metabolites of arenes and benzocycloalkenes of either absolute configuration have been developed using appropriate strains of the bacterium Pseudomonas putida.

  利用适当菌株的铜绿假单胞菌（Pseudomonas putida），已开发出通过酶催化动力学拆分和不对称二羟基化途径制备手性纯顺式二醇代谢物的路线，适用于芳香烃和苯并环烯烃的任一绝对构型。