(1R,2S)-2-(二丁氨基)-1-苯基-1-丙醇 | 115651-77-9

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 氨基醇类衍生物
• 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: (1R,2S)-2-(二丁氨基)-1-苯基-1-丙醇
• 中文别名: (1R,2S)-2-二丁氨基-1-苯基-1-丙醇
• 英文名称: (1R,2S)-(+)-2-(N,N-di-n-butylamino)-1-phenylpropan-1-ol
• 英文别名: (1R,2S)-(+)-2-(N,N-dibutylamino)-1-phenylpropan-1-ol；(1R,2S)-(+)-2-(dibutylamino)-1-phenyl-1-propanol；(1R,2S)-(+)-(dibutylamino)-1-phenyl-1-propanol；(1R,2S)-2-(dibutylamino)-1-phenylpropan-1-ol；(1R,2S)-1-phenyl-2-(dibutylamino)propanol；(1R,2S)-(+)-N,N-dibutylnorephedrine
• CAS: 115651-77-9
• 化学式: C₁₇H₂₉NO
• 分子量: 263.423
• InChiKey: BRRGNOFUBFINSX-RDJZCZTQSA-N

物化性质

• 沸点：
  121 °C0.1 mm Hg(lit.)
• 密度：
  0.944 g/mL at 20 °C(lit.)
• 闪点：
  >230 °F
• 稳定性/保质期：
  避免氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2922199090
• 储存条件：
  请将贮藏器密封保存，并储存在阴凉、干燥的地方。同时，确保工作环境中具有良好通风或排气设施。

SDS

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Section I.Chemical Product and Company Identification
Chemical Name
(1R,2S)-(+)-alpha-[1-(N,N-Di-n-butylamino)ethyl]benzyl
Alcohol
Portland OR
Synonym
(1R,2S)-(+)-N,N-Di-n-butylnorephedrin
Chemical Formula
C 17 H 29 NO
CAS Number
115651-77-9
(International)

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Section II. Composition and Information on Ingredients
Toxicology Data
Chemical Name CAS Number Percent (%) TLV/PEL
(1R,2S)-(+)-alpha-[1-(N,N-Di-n-butylamino)ethyl]benzyl 115651-77-9 Min. 95.0 Not available. Not available.
Alcohol (GC,T)

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Section III. Hazards Identification
Acute Health Effects
Irritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system . Inflam m ation of
the eye is characterized by redness, w atering, and itching. Skin inflam m ation is characterized by itching, scaling,
reddening, or, occasionally, blistering. Follow safe industrial hygiene practices and alw ays w ear proper protective
equipment when handling this compound.
Chronic Health Effects
CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY : Not available.
There is no know n effect from chronic exposure to this product. Repeated or prolonged exposure to this com pound is
not known to aggravate existing medical conditions.

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Section IV. First Aid Measures
Eye Contact
C heck for and rem ove any contact lenses. D O N O T use an eye ointm ent. Flush eyes w ith running w ater for a m inim um
of 15 m inutes, occasionally lifting the upper and low er eyelids. Seek m edical attention. Treat sym ptom atically and
supportively.
Skin Contact
A fter contact w ith skin, w ash im m ediately w ith plen ty of w ater. G ently and thoroughly w ash the contam inated skin w ith
running w ater and non-abrasive soap. Be particularly careful to clean folds, crevices, creases and groin. C over the
irritated skin w ith an em ollient. Seek m edical attention. Treat sym ptom atically and supportively. W ash any
contaminated clothing before reusing.
Inhalation
If the victim is not breathing, perform artificial respiration. Loosen tight clothing such as a collar, tie, belt or w aistband.
If breathing is difficult, oxygen can be administered. Seek medical attention. Treat symptomatically and supportively.
Ingestion
IN D U C E V O M ITIN G by sticking finger in throat. Low er the head so that the vom it w ill not reenter the m outh and throat.
Loosen tight clothing such as a collar, tie, belt, or w aistband. If the victim is not breathing, adm inister artificial
respiration. Exam ine the lips and m outh to ascertain w hether the tissues are dam aged, a possible indication that the
toxic m aterial w as ingested; the absence of such signs, how ever, is not conclusive. Seek im m ediate m edical attention
and, if possible, show the chemical label. Treat symptomatically and supportively.

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Section V. Fire and Explosion Data
Auto-Ignition
Flammability Not available.
Combustible.
Flash Points Flammable Limits
Not available. Not available.
Combustion Products
These products are toxic carbon oxides (CO, CO 2), nitrogen oxides (NO, NO 2 ).
Fire Hazards
No specific information is available regarding the flammability of this compound in the presence of various materials.
Explosion Hazards
Risks of explosion of the product in presence of mechanical impact: Not available.
Risks of explosion of the product in presence of static discharge: Not available.
No additional information is available regarding the risks of explosion.
Fire Fighting Media
SMALL FIRE: Use DRY chemicals, CO 2, water spray or foam.
and Instructions
LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.
Continued on Next Page
115651-77-9nal)(U.S.).ompany Identificationthyl]benzyl Page 2
Alcohol

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Section VI. Accidental Release Measures
Spill Cleanup
Irritating material.
Instructions K eep aw ay from heat and sources of ignition. M echanical exhaust required. Stop leak if w ithout risk. Finish cleaning
the spill by rinsing any contam inated surfaces w ith copious am ounts of w ater. C onsult federal, state, and/or local
authorities for assistance on disposal.

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Section VII. Handling and Storage
Handling and Storage
IRRITA N T. K eep aw ay from heat and sources of ignition. M echanical exhaust required. W hen not in use, tightly seal the
container and store in a dry, cool place. A void excessive heat and light. D O N O T ingest. D o not breathe gas, fum es,
Information
vapor or spray. In case of insufficient ventilation, w ear suitable respiratory equipm ent. If ingested, seek m edical advice
im m ediately and show the container or the label. Treat sym ptom atically and supportively. A void contact w ith skin and
eyes.
Always store away from incompatible compounds such as oxidizing agents.

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Section VIII. Exposure Controls/Personal Protection
Engineering Controls
Provide exhaust ventilation or other engineering controls to keep the airborne concentrations of vapors below their
respective threshold limit value. Ensure that eyewash station and safety shower is proximal to the work-station location.
Personal Protection
Splash goggles. Lab coat. V apor respirator. Boots. G loves. A M SH A /N IO SH approved respirator m ust be used to avoid
inhalation of the product. Suggested protective clothing m ight not be sufficient; consult a specialist BEFO RE handling
this product.
Exposure Limits
Not available.

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Section IX. Physical and Chemical Properties
Physical state @ 20°C Solubility
Liquid.
Not available.
Specific Gravity 0.94 (water=1)
Molecular Weight Partition Coefficient
263.42 Not available.
Boiling Point Vapor Pressure
143 to 145°C (289.4 to 293°F) @ 2mmHg Not available.
Melting Point Vapor Density
Not available. Not available.
Refractive Index Volatility
Not available. Not available.
Critical Temperature Odor
Not available. Not available.
Viscosity Taste
Not available. Not available.

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Section X. Stability and Reactivity Data
Stability

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This material is stable if stored under proper conditions. (See Section VII for instructions)
Conditions of Instability
Avoid excessive heat and light.
Incompatibilities
Reactive with oxidizing agents.

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Section XI. Toxicological Information
RTECS Number
Not available.
Routes of Exposure
Eye contact. Inhalation. Ingestion. Skin contact.
Toxicity Data
Not available.
Chronic Toxic Effects CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY : Not available.
There is no know n effect from chronic exposure to this product. Repeated or prolonged exposure to this com pound is
not known to aggravate existing medical conditions.
Acute Toxic Effects
Irritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system . Inflam m ation of
the eye is characterized by redness, w atering, and itching. Skin inflam m ation is characterized by itching, scaling,
reddening, or, occasionally, blistering. Follow safe industrial hygiene practices and alw ays w ear proper protective
equipment when handling this compound.
Continued on Next Page
(1R,2S)-(+)-alpha-[1-(N,N-Di-n-butylamino)ethyl]benzyl Page 3
Alcohol

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Section XII. Ecological Information
Ecotoxicity
Not available.
Environmental Fate
Not available.

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Section XIII. Disposal Considerations
Waste Disposal
Recycle to process, if possible. C onsult your local or regional authorities. You m ay be able to dissolve or m ix m aterial
w ith a com bustible solvent and burn in a chem ical incinerator equipped w ith an afterburner and scrubber system .
Observe all federal, state, and local regulations when disposing of this substance.

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Section XIV. Transport Information
DOT Classification
Not a DOT controlled material (United States).
PIN Number
Not applicable.
Proper Shipping Name
Not applicable.
Packing Group (PG)
Not applicable.
DOT Pictograms

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Section XV. Other Regulatory Information and Pictograms
TSCA Chemical Inventory T h is p r o d u c t is NOT o n t h e E P A T o x ic S u b s t a n c e s C o n t r o l A c t (T S C A ) in v e n t o r y . T h e f o llo w in g n o t ic e s a r e r e q u ir e d b y 4 0
(EPA) CFR 720.36 (C) for those products not on the inventory list:
(i) These products are supplied solely for use in research and developm ent by or under the supervision of a technically
qualified individual as defined in 40 CFR 720.0 et sec.
(ii) The health risks of these products have not been fully determ ined. A ny inform ation that is or becom es available w ill
be supplied on an MSDS sheet.
WHMIS Classification
WHMIS CLASS D-2A: Material causing other toxic effects (VERY TOXIC).
(Canada)
EINECS Number (EEC)
Not available.
EEC Risk Statements
R36/37/38- Irritating to eyes, respiratory system and skin.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-(二丁氨基)-1-苯基-1-丙醇 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 生成 (1R,2S)-2-Dibutylamino-1-phenyl-propane-1-thiol
  参考文献：
  名称：

  Enantioselective addition of diethylzinc to α-branched aldehydes

  摘要：

  在催化量的(1R,2S)-(–)-1-苯基-2-哌啶丙烷-1-硫醇1存在下，二乙基锌与α-支链醛的反应几乎以100%的外消旋过剩量提供了相应的二级醇。

  DOI：

  10.1039/c39940002009
• 作为产物：
  描述：

  1-碘丁烷 、 去甲麻黄碱 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以56%的产率得到(1R,2S)-2-(二丁氨基)-1-苯基-1-丙醇
  参考文献：
  名称：

  N-甲基麻黄碱修饰的三或四烷基锌酸酯的对称二芳基亚砜的不对称亚磺酰基化

  摘要：

  二乙基锌用1或2当量处理。最好是AlkMgCl或PhMgBr或1当量的AlkMgCl或PhMgBr。的Ñ振振有词锌酸盐- -丁基锂（效率较低），用于形成物种这是由二芳基sulfinylated亚砜，得到外消旋烷基芳基亚砜中的产率达到100％。二烷基锌试剂也可以通过用1或2当量的处理来活化。对映体纯的烷基镁β-氨基醇盐。当醇盐来自二烷基镁试剂和等摩尔量的N-甲基-（-）-麻黄碱时，这种方法最有效。该第二活化模式允许用二芳基亚砜将本来是二烷基锌试剂的亚磺酰基化。这样生成对映体比例高达93：7的烷基芳基亚砜，产率高达100％。

  DOI：

  10.1002/ejoc.201701603
• 作为试剂：
  描述：

  (5S)-5-[(tert-butyldiphenylsilyl)oxy]-6-oxohexyl 4-nitrobenzoate 、 Dimethylzinc 在 (1R,2S)-2-(二丁氨基)-1-苯基-1-丙醇 作用下， 以 甲苯 为溶剂， 反应 18.17h， 生成 (5S,6R)-6-hydroxy-5-terbutyldiphenyl silyloxyheptyl 4-nitrobenzoate 、 (5S,6S)-6-hydroxy-5-tert-butyldiphenylsilyloxyheptyl 4-nitrobenzoate
  参考文献：
  名称：

  [EN] QUINONE BASED NITRIC OXIDE DONATING COMPOUNDS FOR OPHTHALMIC USE
  [FR] COMPOSÉS DONNEURS D'OXYDE NITRIQUE À BASE DE QUINONE À USAGE OPHTALMIQUE

  摘要：

  本发明涉及一种具有以醌为基础结构的一氧化氮供体化合物，其化学式为(I)，其中R1至R6、n、m和p如权利要求1中所定义，以及这些化合物的组合物，用于治疗和/或预防青光眼和眼压增高。

  公开号：

  WO2014170264A1

文献信息

• [EN] QUINONE BASED NITRIC OXIDE DONATING COMPOUNDS<br/>[FR] COMPOSÉS DONNEURS D'OXYDE NITRIQUE À BASE DE QUINONE
  申请人：NICOX SCIENCE IRELAND

  公开号：WO2014169976A1

  公开（公告）日：2014-10-23

  The present invention relates to nitric oxide donor compounds having a quinone based structure, to processes for their preparation and to their use in the treatment of pathological conditions where a deficit of NO plays an important role in their pathogenesis.

  本发明涉及具有醌基结构的一氧化氮供体化合物，以及它们的制备过程和它们在治疗病理条件中的应用，其中一氧化氮缺乏在它们的发病机制中起重要作用。
• An Efficient Synthesis of Enantiopure 1-Alkoxy-1,2-propadienes from Propargyl Bromide
  作者：Patrick Rochet、Jean-Michel Vatèle、Jacques Goré

  DOI：10.1055/s-1994-25577

  日期：——

  A number of enantiopure functionalized alcohols have been O-allenylated by reaction of their corresponding sodium alcoholates with propargyl bromide followed by t-BuOK catalyzed isomerization of the resulting propargyl ethers, in good overall yields.

  一系列对映纯功能化醇通过其相应钠醇盐与丙炔溴化物反应后，再经过t-BuOK催化的异构化反应，对得到的丙炔醚进行O-烯丙基化，获得了良好的总体产率。
• Reactions of Amino Alcohols in Superacid:  The Direct Observation of Dicationic Intermediates and Their Application in Synthesis
  作者：Douglas A. Klumpp、Sharon L. Aguirre、Gregorio V. Sanchez、Sarah J. de Leon

  DOI：10.1021/ol016408y

  日期：2001.8.1

  [reaction: see text]. The chemistry of amino alcohols has been studied in superacidic media, and these compounds have been found to ionize cleanly to the dication intermediates. Several dicationic species have been directly observed by low-temperature 13C NMR, including those from epinephrine (adrenaline) and synephrine. Amino alcohols react (70-99% yields) with C6H6 in triflic acid (CF3SO3H) by electrophilic

  [反应：请参见文字]。氨基醇的化学性质已在超酸性介质中进行了研究，发现这些化合物可清洁地离子化成指示剂中间体。通过低温13 C NMR直接观察到了几种药物，包括肾上腺素（肾上腺素）和肾上腺素的药物。氨基醇通过亲电子芳族取代与三氟甲磺酸（CF3SO3H）中的C6H6反应（产率70-99％）。
• Enantioselective addition of diethylzinc to aldehydes in the presence of chiral aprotic ligands
  作者：Myung-Jong Jin、Young-Mok Kim、Kyoung-Soo Lee

  DOI：10.1016/j.tetlet.2005.02.066

  日期：2005.4

  Optically active amino thiocyanate derivatives of (−)-norephedrine were found to act as effective aprotic ligands for enantioselective addition of diethylzinc to aldehydes. This reaction provided optically active secondary alcohols with ee up to 96%.

  发现（-）-去氧麻黄碱的旋光性氨基硫氰酸酯衍生物可作为有效的非质子传递配体，用于将二乙基锌对映体选择性地加成成醛。该反应提供了具有高达96％ee的旋光仲醇。
• Effect of Ligand Structure on the Asymmetric Cyclization of Achiral Olefinic Organolithiums
  作者：Michael J. Mealy、Matthew R. Luderer、William F. Bailey、Michael Bech Sommer

  DOI：10.1021/jo049477+

  日期：2004.9.1

  The ability of a large and chemically diverse set of 30 chiral ligands to effect asymmetric cyclization of 2-(N,N-diallylamino)phenyllithium (1), derived from N,N-diallyl-2-bromoaniline (2) by low-temperature lithium−bromine exchange, has been investigated in an attempt to elucidate the structural motifs required to provide high enantiofacial selectivity in the ring closure. Although none of the ligands

  大量化学性质多样的30个手性配体通过低温影响N，N-二烯丙基-2-溴苯胺（2）衍生的2-（N，N-二烯丙基氨基）苯基锂（1）的不对称环化的能力研究了溴溴化锂的交换，以阐明在闭环中提供高对映面部选择性所需的结构基序。尽管在本研究中检查的任何配体均未提供比以前观察到的1环化显着更高的ee的1-allyl-3-methylindoline 在基准配体（-）-天冬氨酸的存在下，发现一些结构上与斯巴汀无关的配体以对映体形式存在，它们与（-）-天冬氨酸在该化学中的效用匹配。