(1S,2s)-(+)-n-甲基伪麻黄碱 | 1201-56-5

• 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: (1S,2s)-(+)-n-甲基伪麻黄碱
• 中文别名: (1S,2S)-(+)-N-甲基-Ψ-麻黄碱；(1S,2S)-2-二甲氨基-1-苯丙醇；(1S,2S)-2-二甲基氨基-1-苯丙醇；(+)-N-甲基伪麻黄碱
• 英文名称: (1S,2S)-N-Methylpseudoephedrine
• 英文别名: (1S,2S)-2-(dimethylamino)-1-phenylpropan-1-ol
• CAS: 1201-56-5；14222-20-9；17605-71-9；39263-91-7；42151-56-4；51018-28-1；62560-55-8；87040-40-2；552-79-4
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: FMCGSUUBYTWNDP-GXSJLCMTSA-N

物化性质

• 熔点：
  63.5-64.5 °C
• 沸点：
  82-92 °C(Press: 2 Torr)
• 密度：
  1.009±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  熔点为63.5℃（-64.5℃）。其盐酸盐为白色针状结晶或结晶性粉末，熔点为207℃（-208℃）。易溶于水、乙醇、冰乙酸，微溶于氯仿或丙酮。无臭，味苦。

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 储存条件：
  冰箱温度为4℃

SDS

Name:	(-)-N-Methylephedrine, 99% Material Safety Data Sheet
Synonym:	(-)-alpha-[1-(Dimethylamino)ethyl]benzenemethanol; (-)-(1R,2S)-2-Dimethylamino-1-phenyl-1-propanol; Ephedrine, N-methyl-
CAS:	552-79-4

Section 1 - Chemical Product MSDS Name: (-)-N-Methylephedrine, 99% Material Safety Data Sheet
Synonym: (-)-alpha-[1-(Dimethylamino)ethyl]benzenemethanol; (-)-(1R,2S)-2-Dimethylamino-1-phenyl-1-propanol; Ephedrine, N-methyl-

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SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
552-79-4	(-)-N-Methylephedrine	99	209-022-7

Hazard Symbols: XN
Risk Phrases: 22 36/37/38

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SECTION 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Harmful if swallowed. Irritating to eyes, respiratory system and skin.Hygroscopic (absorbs moisture from the air).Light sensitive. Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May cause central nervous system stimulation.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
Chronic:
No information found.

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SECTION 4 - FIRST AID MEASURES
Eyes:
Immediately 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. Remove contaminated clothing and shoes.
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. Wash mouth out with 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:
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 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:
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. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation. Store protected from light. Keep from contact with moist air and steam.
Storage:
Store in a tightly closed container. Keep refrigerated. (Store below 4C/39F.) Store protected from moisture. Store protected from light.

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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# 552-79-4: 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: Crystals
Color: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 85-88 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Not available.
Specific Gravity/Density: Not available.
Molecular Formula: C11H17NO
Molecular Weight: 179.26

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SECTION 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures. Sensitive to light.
Hygroscopic: absorbs moisture or water from the air.
Conditions to Avoid:
Incompatible materials, light, dust generation, exposure to moist air or water.
Incompatibilities with Other Materials:
Acid chlorides, acid anhydrides, acids, oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 552-79-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(-)-N-Methylephedrine - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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SECTION 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 22 Harmful if swallowed. R 36/37/38 Irritating to eyes, respiratory system and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 37/39 Wear suitable gloves and eye/face protection. WGK (Water Danger/Protection) CAS# 552-79-4: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 552-79-4 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 552-79-4 is not listed on the TSCA inventory. It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 9/02/1997 Revision #8 Date: 2/10/2005 The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

合成制备方法

将伪麻黄碱的结晶母液蒸发浓缩，得到的沉淀物加8倍水煮沸半小时后充分自然冷却，分离析出的结晶并用水冲洗，得混合麻黄碱粗品。将粗品加水加热溶解，调节pH值至7，并用盐酸处理脱色。再加入饱和氯化钙溶液除草酸盐，加入饱和硫化钠溶液除铁盐，搅拌5分钟后静置8小时，滤除杂质。滤液中加入盐酸调pH值至6-6.5，再加活性炭脱色一次后滤除炭渣。将滤液减压浓缩、放冷结晶、分离，并用蒸馏水重结晶，最终得到甲基麻黄碱盐酸盐。

用途

该品具有类似麻黄碱盐酸盐扩张支气管的作用，且有更强的抗过敏和镇咳作用，而无麻黄碱盐酸盐兴奋中枢、加速心率与升高血压等作用。适用于治疗流行性感冒、支气管哮喘、过敏反应等症状。

反应信息

• 作为反应物：
  描述：

  (1S,2s)-(+)-n-甲基伪麻黄碱 在 hexamethyldisilazide 作用下， 以 苯 为溶剂， 生成 lithium N-methylpseudoephedrate
  参考文献：
  名称：

  Arnett, Edward M.; Nichols, Michael A.; McPhail, Andrew T., Journal of the American Chemical Society, 1990, vol. 112, # 19, p. 7059 - 7060

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4beta-二甲基-5alpha-苯基恶唑烷-2-酮 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到(1S,2s)-(+)-n-甲基伪麻黄碱
  参考文献：
  名称：

  Facile inversion of configuration of N-Boc-β-aminoalcohols via SN2 cyclization to oxazolidinones

  摘要：

  Oxazolidinones are obtained by the cyclization of mesylates derived from N-Boc-beta -aminoalcohols. Hydrolysis of the N-Boc-oxazolidinones regenerates the protected aminoalcohols with inverted configuration at the hydroxy group. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01753-6
• 作为试剂：
  描述：

  2,2-二甲基-1,3-环己烷二酮 在 2-溴吡啶-1-氧化物 、 过氧乙酸 、 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 硫酸 、 camphor-10-sulfonic acid 、 C₁₈H₁₅AuP⁽¹⁺⁾*C₂F₆NO₄S₂^(1-)*C₇H₈ 、 (1S,2s)-(+)-n-甲基伪麻黄碱 、 四丁基氟化铵 、 双氧水 、 diethylzinc 、 氧气 、 三乙基铝 、 copper(l) cyanide 、 4-甲基苯磺酸吡啶 、 L-Selectride 、 sodium hydride 、 sodium carbonate 、 caesium carbonate 、 magnesium 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 二异丙胺 、 原甲酸三乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 1,2-二溴乙烷 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 531.7h， 生成 [(3R,3'aR,6'S,8'R,9'aR,10'aS)-7-[(2R)-3,3-dimethyloxirane-2-carbonyl]-10'a-hydroxy-1',1',6'-trimethyl-3'a-(methylamino)-2-oxospiro[1H-indole-3,2'-3,4,6,7,8,9,9a,10-octahydrocyclopenta[b]quinolizine]-8'-yl] (2S)-2-(dimethylamino)-3-methylbutanoate 、 (S)-(2R,3aR,6S,8R,9aR,10aS)-7'-((S)-3,3-dimethyloxirane-2-carbonyl)-10a-hydroxy-1,1,6-trimethyl-3a-(methylamino)-2'-oxo-3,3a,4,6,7,8,9,9a,10,10a-decahydro-1H-spiro[cyclopenta[b]quinolizine-2,3'-indolin]-8-yl-2-(dimethylamino)-3-methylbutanoate
  参考文献：
  名称：

  (-)-Citrinadin A的对映选择性全合成及其立体化学结构的修正

  摘要：

  (-)-citrinadin A 的第一个对映选择性全合成是通过 20 个步骤从市售材料通过最小化再官能化和保护/脱保护操作的方法完成的。该合成的基石是将二烯醇盐不对称地加成到手性吡啶鎓盐中以设置初始手性中心。一系列底物控制的反应，包括高度立体选择性环氧化/开环序列和吲哚的氧化重排以提供螺吲哚，然后用于在 (-)-citrinadin A 的五环核心中建立剩余的立体中心。 citrinadin A 的成功合成导致了citrinadin 核心亚结构立体化学结构的修订。

  DOI：

  10.1021/ja405547f

文献信息

• [EN] PROCESS FOR THE SYNTHESIS OF CYCLIC CARBAMATES<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE CARBAMATES CYCLIQUES
  申请人：LONZA AG

  公开号：WO2012048884A1

  公开（公告）日：2012-04-19

  The invention is directed to a process for the preparation of a cyclic carbamate starting with a chiral propargylic alcohol and/or a suitable salt thereof, which is reacted with a cyclisation agent selected from phosgene, diphosgene, triphosgene and mixtures thereof, and in that the reaction is carried out in the presence of an aqueous base, and a water-immiscible organic solvent, said organic solvent mainly comprising at least one compound selected from C2-5-alkyl C2-5-carboxylates and mixtures of at least one C2-5-alkyl C2-5-carboxylate with at least one C5-8-alkane. Another aspect of the invention is directed to a process for the synthesis of said cyclic carbamate starting described above, wherein also a process for the preparation of the chiral propargylic alcohol is provided.

  本发明涉及一种以手性炔丙醇和/或适当的盐为起始物，通过选择光气、二光气、三光气及其混合物作为环化剂进行反应，以制备环状碳酸酯的方法，其中反应在水性碱和与水不混溶的有机溶剂的存在下进行，所述有机溶剂主要由至少一种C2-5-烷基C2-5-羧酸酯和至少一种C2-5-烷基C2-5-羧酸酯与至少一种C5-8-烷烃的混合物组成。发明的另一方面涉及上述描述的环状碳酸酯的合成过程，其中还提供了制备手性炔丙醇的方法。
• Enantioselective and Diastereoselective Construction of Chiral Amino Alcohols by Iridium–f-Amphox-Catalyzed Asymmetric Hydrogenation via Dynamic Kinetic Resolution
  作者：Weilong Wu、Cai You、Congcong Yin、Yuanhua Liu、Xiu-Qin Dong、Xumu Zhang

  DOI：10.1021/acs.orglett.7b00844

  日期：2017.5.19

  The iridium–f-amphox-catalyzed asymmetric hydrogenation of racemic α-amino β-unfunctionalized ketones proceeds via a DKR (dynamic kinetic resolution) process for the construction of various chiral N,N-disubstituted α-amino β-unfunctionalized alcohols in quantitative yields with excellent enantioselectivities and diastereoselectivities (all products >99% ee and >99:1 dr, TON up to 100 000). Importantly

  外消旋α-氨基β-非官能化酮的铱-f-amphox催化的不对称氢化通过DKR（动态动力学拆分）过程进行，以定量产率构建各种手性N，N-二取代的α-氨基β-非官能化醇具有出色的对映选择性和非对映选择性（所有产品> 99％ee和> 99：1 dr，TON高达100000）。重要的是，这种采用DKR方法的催化不对称氢化为制备临床前抗肿瘤剂（S，S）-R116010的关键手性中间体提供了高效且强大的合成策略。
• Regio- and Stereospecific Syntheses of <i>syn-</i> and <i>anti-</i>1,2-Imidazolylpropylamines from the Reaction of 1,1‘-Carbonyldiimidazole with <i>syn-</i> and <i>anti-</i>1,2-Amino Alcohols
  作者：Mark J. Mulvihill、Cara Cesario、Vanessa Smith、Patricia Beck、Anthony Nigro

  DOI：10.1021/jo049677l

  日期：2004.7.1

  The regio- and stereospecific conversion of syn- and anti-1,2-amino alcohols to their respective syn- and anti-1,2-imidazolylpropylamines via treatment with 1,1‘-carbonyldiimidazole is described. The rationale behind the regio- and stereospecific nature as well as the generality of the reaction is discussed.

  描述了通过用1，1'-羰基二咪唑处理将顺式和反式-1,2-氨基醇的区域和立体特异性转化为它们各自的顺式和反式-1,2-咪唑基丙胺。讨论了区域特异性和立体特异性本质以及反应一般性的基本原理。
• Kinase inhibitors
  申请人：——

  公开号：US20030187026A1

  公开（公告）日：2003-10-02

  Compounds having the formula 1 are useful for inhibiting protein kinases. Also disclosed are compositions which inhibit protein kinases and methods of inhibiting protein kinases in a patient.

  具有以下化学式的化合物对抑制蛋白激酶很有用。还公开了抑制蛋白激酶的组合物以及在患者中抑制蛋白激酶的方法。
• Structural optimization of thiourea-based bifunctional organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones
  作者：Albrecht Berkessel、Santanu Mukherjee、Thomas N. Müller、Felix Cleemann、Katrin Roland、Marc Brandenburg、Jörg-M. Neudörfl、Johann Lex

  DOI：10.1039/b607574f

  日期：——

  describes the synthesis of a library of structurally diverse bifunctional organocatalysts bearing both a quasi-Lewis acidic (thio)urea moiety and a Bronsted basic tertiary amine group. Sequential modification of the modular catalyst structure and subsequent screening of the compounds in the alcoholytic dynamic kinetic resolution (DKR) of azlactones revealed valuable structure-activity relationships. In particular

  本文介绍了结构多样的双功能有机催化剂库的合成，该催化剂同时具有准路易斯酸（硫）脲部分和布朗斯台德碱性叔胺基团。模块化催化剂结构的顺序修饰和随后的内酯​​内醇动力学动力学拆分（DKR）中的化合物的筛选揭示了宝贵的结构-活性关系。特别地，鉴定出“命中结构”，其以优异的对映体过量95％提供例如N-苯甲酰基-叔亮氨酸烯丙基酯。