(R)-(+)-N-苯甲酰-Alpha-甲基苯胺 | 20826-48-6

• 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)-(+)-N-苯甲酰-Alpha-甲基苯胺
• 中文别名: (R)-(+)-N-苯甲酰-Α-甲基苯胺；(R)-(+)-n-苯甲酰基-alpha-甲基苄胺；(R)-(+)-N-苯甲酰-α-甲基苯胺
• 英文名称: (R)-N-(1-phenylethyl)benzamide
• 英文别名: N-(1-phenylethyl)benzamide；(R)-N-benzoyl-1-phenylethylamine；N-[(1R)-1-phenylethyl]benzamide
• CAS: 20826-48-6
• 化学式: C₁₅H₁₅NO
• mdl: MFCD03427637
• 分子量: 225.29
• InChiKey: FALTVGCCGMDSNZ-GFCCVEGCSA-N

物化性质

• 熔点：
  123-125 °C
• 沸点：
  422.8±24.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2924299090
• 储存条件：
  存放在阴凉干燥处即可。

SDS

Name:	(R)-(+)-N-Benzoyl-alpha-methylbenzylamine Material Safety Data Sheet
Synonym:	N-[(1R)-1-Phenylethyl]benzamide
CAS:	20826-48-6

Section 1 - Chemical Product MSDS Name:(R)-(+)-N-Benzoyl-alpha-methylbenzylamine Material Safety Data Sheet
Synonym:N-[(1R)-1-Phenylethyl]benzamide

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
20826-48-6	(R)-(+)-N-Benzoyl-alpha-methylbenzylam	100	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. 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. 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 chemical 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. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. 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:
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# 20826-48-6: 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: Crystalline powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 123 - 125 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Insoluble.
Specific Gravity/Density:
Molecular Formula: C15H15NO
Molecular Weight: 225.29

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 20826-48-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(R)-(+)-N-Benzoyl-alpha-methylbenzylamine - 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.
WGK (Water Danger/Protection)
CAS# 20826-48-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 20826-48-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 20826-48-6 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)-(+)-N-苯甲酰-Alpha-甲基苯胺 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-(+)-N-苄基-1-苯乙胺
  参考文献：
  名称：

  结合磁共振光谱、质谱和分子动力学：研究 2,6-二-O-甲基-β-环糊精的手性识别

  摘要：

  EPR 光谱已被用于研究 heptakis-(2,6-O-二甲基)-β-环糊精 (DM-β-CD) 和不同对映异构体对的通用结构 PhCH2NO.CH(R) 手性氮氧化物之间的复合物的形成R'。自由基和所含自由基浓度的准确平衡测量提供了这些氮氧化物的结合常数值。DM-β-CD 复合物的立体化学与复合热力学之间的关系通过将 EPR 数据与 1H-1H NOE 测量相关联，对 DM-β-CD 和结构相关的硝基氧胺前体之间的复合物进行了测量。NOE 数据表明，仅当与手性碳相连的 R 取代基包含芳香环时，才会在 DM-β-CD 腔中包含立体中心。对于这些类型的复合物，分子动力学模拟表明立体中心渗透到环糊精腔中的深度由不对称碳上的第二个取代基 (R') 的性质决定，并且是观察到的手性选择性的原因。质谱分析表明，对于目前研究的胺，通过 ESI-MS 检测到 CD 与质子化胺的静电外部加合物。

  DOI：

  10.1021/ja049713y
• 作为产物：
  描述：

  1,1-diphenyl-N-[(1R)-1-phenylethyl]methanimine 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 (R)-(+)-N-苯甲酰-Alpha-甲基苯胺
  参考文献：
  名称：

  铜催化加氢胺化合成手性伯胺的实用亲电氮源

  摘要：

  在烯烃和炔烃之间催化安装氨基的温和实用方法长期以来一直被认为是合成化学中的重大挑战。由于使用氨直接对烯烃加氢胺化需要苛刻的条件，因此为正式加氢胺化方法开发合适的亲电胺化试剂具有重要意义。在此，我们描述了使用 1,2-苯并异恶唑作为实用的亲电伯胺源。使用这种杂环作为新的氨基传递剂，开发了一种温和的通用方案，用于氢化铜催化烯烃和炔烃的加氢胺化以形成伯胺。该方法提供了获得广泛的手性 α-支化伯胺和线性伯胺的途径，

  DOI：

  10.1021/jacs.8b10564

文献信息

• Sulfated tungstate: a highly efficient catalyst for transamidation of carboxamides with amines
  作者：Sagar P. Pathare、Ashish Kumar H. Jain、Krishnacharya G. Akamanchi

  DOI：10.1039/c3ra00127j

  日期：——

  An environmentally benign protocol for the transamidation of carboxamides with amines using sulfated tungstate, as a heterogeneous catalyst, has been developed. The method has been successfully applied to the synthesis of a wide range of aromatic and aliphatic amides and phthalimides. Efficient transformation, mild reaction conditions, easy product isolation and the potential reusability of the catalyst

  已经开发出一种环境友好的方案，用于使用硫酸化钨酸盐作为非均相催化剂将羧酰胺与胺进行氨基转移。该方法已成功应用于多种芳族和脂族酰胺和邻苯二甲酰亚胺的合成。高效的转化，温和的反应条件，容易的产物分离和催化剂的潜在可重复使用性是吸引人的特征。
• Zirconium Oxide‐Catalyzed Direct Amidation of Unactivated Esters under Continuous‐Flow Conditions
  作者：Md. Nurnobi Rashed、Koichiro Masuda、Tomohiro Ichitsuka、Nagatoshi Koumura、Kazuhiko Sato、Shū Kobayashi

  DOI：10.1002/adsc.202001496

  日期：2021.5.18

  A sustainable and environmentally benign direct amidation reaction of unactivated esters with amines has been developed in a continuous-flow system. A commercially available amorphous zirconium oxide was found to be an efficient catalyst for this reaction. While the typical amidation of esters with amines requires a stoichiometric amount of a promoter or metal activator, the present continuous-flow

  在连续流系统中，已开发出未活化的酯与胺的可持续的，对环境无害的直接酰胺化反应。发现可商购的无定形氧化锆是该反应的有效催化剂。尽管典型的酯与胺的酰胺化反应需要化学计量的助催化剂或金属活化剂，但本发明的连续流方法能够在无添加剂的条件下进行直接酰胺化反应，并且对各种官能团具有广泛的多样性。用几乎等摩尔比例的原料获得高收率的产品，以减少副产物的形成，这使得该方法适用于连续流系统。
• [EN] PYRROLE COMPOUNDS FOR THE TREATMENT OF PROSTAGLANDIN MEDIATED DISEASES<br/>[FR] COMPOSES PYRROLIQUES DESTINES AU TRAITEMENT DE MALADIES INDUITES PAR PROSTAGLANDINE
  申请人：GLAXO GROUP LTD

  公开号：WO2003101959A1

  公开（公告）日：2003-12-11

  Compounds of formula (I) or a pharmaceutically acceptable derivative thereof: wherein A, R1, R2a, R2b, Rx, R8, and R9 are as defined in the specification, a process for the preparation of such compounds, pharmaceutical compositions comprising such compounds and the use of such compounds in medicine, in particular their use in the treatment of prostaglandin mediated diseases such as pain, inflammatory, immunological, bone, neurodegenerative or renal disorder.

  式(I)的化合物或其药学上可接受的衍生物：其中A、R1、R2a、R2b、Rx、R8和R9如规范中所定义，一种制备这种化合物的方法，包括这种化合物的药物组合物以及这种化合物在医学中的用途，特别是它们在治疗前列腺素介导的疾病，如疼痛、炎症、免疫、骨骼、神经退行性或肾脏疾病中的用途。
• [EN] PIPERIDINETRIOL DERIVATIVES AS INHIBITORS OF GLYCOSYLCERAMIDE SYNTHASE<br/>[FR] UTILISATION DE DERIVES DU PIPERIDINETRIOL EN TANT QU'INHIBITEURS DE LA GLYCOSYLCERAMIDE SYNTHASE
  申请人：OXFORD GLYCOSCIENCES UK LTD

  公开号：WO2004007453A1

  公开（公告）日：2004-01-22

  Compounds of formula (I): wherein R represents various substituent groups, are useful as inhibitors of glucosylceramide synthase.

  式（I）的化合物：其中R代表各种取代基团，可用作葡萄糖酰胺合成酶的抑制剂。
• Kinetic resolution of amines with enantiopure 3-N,N-diacylaminoquinazolin-4(3H)-ones
  作者：Al-Sehemi, Abdullah G.、Atkinson, Robert S.、Fawcett, John

  DOI：10.1039/b105917n

  日期：2002.1.7

  The title compounds (DAQs) are chiral when the two N-acyl groups are different because of the absence of rotation around the N–N bond (a chiral axis). Enantiopure DAQs have been obtained by incorporation of a chiral centre in enantiopure form either into the substituent at the Q2-position or into one of the N-acyl groups, or into both, followed by separation of diastereoisomers. This separation is unnecessary in one case because conversion of the N-monoacylaminoquinazolinone (MAQ) into the DAQ is completely diastereoselective. Neither is separation of diastereoisomers necessary with 3-[N,N-di-(S)-2-acetoxypropanoylamino]-2-diphenylmethylquinazolin-4(3H)-one 37a: this DAQ 37a has its N–N bond rendered a chiral axis by the bias in its imide moiety wholly in favour of one exo/endo conformation.The high chemoselectivity exhibited by N,N-diacetyl- or N,N-dibenzoylaminoquinazolinones in reaction with the less hindered of two secondary amines (pyrrolidine in the presence of 1 eq. of piperidine) has a stereoselective counterpart: reaction of the above enantiopure DAQs enantioselectively with racemic amines leading to kinetic resolution. Using 1 eq. of DAQ and 2 eq. of amine, both the derivatised and unreacted amine enantiomers are recovered with high enantiomeric excess (ee) (better than 90% ee in some cases). Some of the higher ees are found in the recovered amides where non-chemoselective attack on both N-acyl groups of the DAQ has occurred: from the opposite configurations of the amine component in the two amides and from the low enantiopurity of the recovered unreacted amine, reaction of each of the N-acyl groups with complementary enantiomers of the amine is occurring (parallel kinetic resolution).Although higher ees are, in general, obtained using secondary amines, high ees are obtained in some cases using 1-phenylethylamine and, in particular, amino acid esters (valine and alanine).The sense of enantioselectivity in the reactions of these DAQs with amines is controlled by the configuration of the N–N axis: replacing the Q group in an N-(S)-2-acetoxypropanoyl-N-acetyl-bearing DAQ by phthalimide, thus eliminating the N–N chiral axis, drastically reduces the level of kinetic resolution.

  标题化合物(DAQs)在两个N-酰基团不同时是手性的，因为N-N键（一个手性轴）缺乏旋转。通过将手性中心以手性形式引入Q2-位点的取代基或其中一个N-酰基团，或两者中，随后分离diastereoisomers，得到了纯对映体的DAQs。在一个情况下，这种分离是不必要的，因为将N-单酰胺基喹唑啉酮(MAQ)转化为DAQ是完全立体选择性的。对于3-[N,N-di-(S)-2-乙酰氧基丙酰胺基]-2-二苯甲基喹唑啉-4(3H)-酮37a，也不需要分离diastereoisomers：这个DAQ 37a通过其亚胺部分的偏向完全倾向于一个exo/endo构象，使其N-N键成为一个手性轴。N,N-二乙酰基或N,N-二苯甲酰氨基喹唑啉酮在与两个次级胺中较少受到阻碍的胺（在存在1 eq.的哌啶的情况下使用吡咯烷）反应时表现出高度的化学选择性，这在立体选择性上有对应：上述纯对映体的DAQs与外消旋胺反应，导致动力学拆分。使用1 eq.的DAQ和2 eq.的胺，衍生化的和未反应的胺对映体都以高对映体过量（ee）回收（在一些情况下优于90% ee）。在一些回收的酰胺中发现较高的ee，其中非化学选择性地攻击DAQ的两个N-酰基团：从两个酰胺中胺组分的相反构型和回收的未反应胺的低对映纯度，每个N-酰基团与胺的互补对映体反应（并行动态拆分）。尽管通常使用次级胺得到较高的ee，但在某些情况下使用1-苯乙胺，特别是氨基酸酯（缬氨酸和丙氨酸）得到高ee。这些DAQs与胺反应的对映选择性的方向受N-N轴配置的控制：在带有N-(S)-2-乙酰氧基丙酰基-N-乙酰基的DAQ中，通过用邻苯二甲酰亚胺替换Q组，从而消除N-N手性轴，显著降低了动力学拆分的水平。