(R)-2- [N-(N-苄基脯氨酰）氨基]二苯甲酮 | 96293-17-3

• 物质功能分类: 生物化工 - 生化试剂 - 其他生化试剂
• 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- [N-(N-苄基脯氨酰）氨基]二苯甲酮
• 中文别名: (R)-2-[N'-(N-苄基脯氨酰)氨基]二苯甲酮；(S)-2-[N'-(N-苄基脯氨酰)氨基]二苯甲酮；(R)-2-[N-(N-苄基脯氨酰）氨基]二苯甲酮；(R)-2- [N'-(N-苄基脯氨酰)氨基]二苯甲酮
• 英文名称: (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide
• 英文别名: (S)-2-[N-(N'-benzylprolyl)amino]benzophenone；(2S)-N-(2-benzoylphenyl)-1-benzyl-pyrrolidine-2-carboxamide；(2S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide
• CAS: 96293-17-3
• 化学式: C₂₅H₂₄N₂O₂
• mdl: MFCD00145260
• 分子量: 384.478
• InChiKey: IPSABLMEYFYEHS-QHCPKHFHSA-N

物化性质

• 熔点：
  100-103 °C
• 沸点：
  511.14°C (rough estimate)
• 密度：
  1.1573 (rough estimate)
• 最大波长(λmax)：
  240nm(MeOH)(lit.)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  2933 99 80
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存放于阴凉干燥处。

SDS

Name:	(S)-2-n -(N-Benzylprolyl)AminoBenzo-Phenone 99.5+% Material Safety Data Sheet
Synonym:	None known
CAS:	96293-17-3

Section 1 - Chemical Product MSDS Name:(S)-2-n -(N-Benzylprolyl)AminoBenzo-Phenone 99.5+% Material Safety Data Sheet
Synonym:None known

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
96293-17-3	(S)-2-[N'-(N-Benzylprolyl)Amino!benzo-	99.5+	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

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.

---

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.
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:

---

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. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

---

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.

---

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:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

---

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# 96293-17-3: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: slightly yellow
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 101.00 - 102.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: insoluble
Specific Gravity/Density:
Molecular Formula: C25H24N2O2
Molecular Weight: 384.47

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 96293-17-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(S)-2-[N'-(N-Benzylprolyl)Amino!benzo-Phenone - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

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.

---

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# 96293-17-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 96293-17-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 96293-17-3 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (R)-2- [N-(N-苄基脯氨酰）氨基]二苯甲酮 在 氰基亚甲基三正丁基膦 、 potassium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 1.0h， 生成 (S)-3-(2-(benzyloxy)phenyl)-2-(((E)-(2-((S)-1-benzylpyrrolidine-2-carboxamido)phenyl)(phenyl)methylene)amino)propanoate-1-13C
  参考文献：
  名称：

  自我掩蔽的醛抑制剂：抑制半胱氨酸蛋白酶的新策略

  摘要：

  半胱氨酸蛋白酶是一类重要的药物靶点，特别是针对恰加斯病 (cruzain) 和 COVID-19（3CL 蛋白酶、组织蛋白酶 L）等传染病。肽醛已被证明是所有这些蛋白酶的有效抑制剂。然而，醛基固有的高亲电性与安全问题和代谢不稳定相关，限制了醛抑制剂作为药物的使用。我们针对 cruzain 开发了一类新型自掩醛抑制剂 (SMAIs)，cruzain 是恰加斯病病原体克氏锥虫的主要半胱氨酸蛋白酶。这些 SMAI 对 cruzain 发挥有效、可逆的抑制作用（K i * = 18–350 nM），同时在细胞检测中明显保护游离醛。我们合成了 SMAI 的前药，有可能改善其药代动力学特性。我们还阐明了 SMAI 的动力学和化学机制，并将该策略应用于抗 SARS-CoV-2 抑制剂的设计。

  DOI：

  10.1021/acs.jmedchem.1c00628
• 作为产物：
  描述：

  在 乙二胺四乙酸 、 肼 、 盐酸 作用下， 以 乙醇 、 水 、 甲醇 为溶剂， 反应 6.0h， 以96%的产率得到(R)-2- [N-(N-苄基脯氨酰）氨基]二苯甲酮
  参考文献：
  名称：

  Enantioselective Synthesis of 2-Substitued-Tetrahydroisoquinolin-1-yl Glycine Derivatives via Oxidative Cross-Dehydrogenative Coupling of Tertiary Amines and Chiral Nickel(II) Glycinate

  摘要：

  The asymmetric synthesis of 2-substituted-tetrahydroisoquinolin-1-yl glycines was achieved by an oxidative cross-dehydrogenative coupling (CDC) reaction. This method for activation of the alpha-C-H bonds of amines with chiral nickel(II) glycinate using o-chloranil as the sole oxidant afforded highly diastereoselective coupling adducts. The decomposition of coupling adducts readily afforded 2-substituted-tetrahydroisoquinolin-1-yl glycine derivatives.

  DOI：

  10.1021/jo401510b
• 作为试剂：
  描述：

  2-氨基乙醛 、 ethyl (4-methoxyphenylimino)acetate 在 nickel(II) nitrate hexahydrate 、 (R)-2- [N-(N-苄基脯氨酰）氨基]二苯甲酮 、 sodium hydride 、 potassium hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸 、 水 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.5h， 以96%的产率得到(2S,3R)-2-amino-4-ethoxy-3-(4-methoxyphenylamino)-4-oxobutanoic acid
  参考文献：
  名称：

  手性甘氨酸镍（II）与α-氨基酯的高度对映和非对映选择性曼尼希反应，用于不对称合成3-氨基天冬氨酸

  摘要：

  在1存在下，甘氨酸席夫碱的手性镍（II）配合物与N-（对甲氧基苯基）保护的α-亚氨基酯的高度对映和非对映选择性曼尼希反应合成了3-氨基天冬氨酸酯。室温下，1，8-二氮杂双环[5.4.0]十一碳-7-烯和二氯甲烷。该步骤导致产物具有高达99％的非对映异构体过量和优异的产率。 氨基酸-不对称合成-氨基天冬氨酸

  DOI：

  10.1055/s-0029-1219275

文献信息

• Synthesis of Chiral Spin-Labeled Amino Acids
  作者：Wayne Vuong、Fabricio Mosquera-Guagua、Randy Sanichar、Tyler R. McDonald、Oliver P. Ernst、Lei Wang、John C. Vederas

  DOI：10.1021/acs.orglett.9b04216

  日期：2019.12.20

  Spin-labeled amino acids (SLAAs) are often used to determine intermolecular distances and conformations in proteins via double electron-electron resonance. Currently available SLAAs can be difficult to incorporate selectively and have little resemblance to natural side chains in proteins. Enantioselective synthesis of three spin-labeled l-amino acids is described, starting from readily available 2

  自旋标记氨基酸（SLAA）通常用于通过双电子-电子共振确定分子间的距离和蛋白质构象。当前可用的SLAA可能难以选择性地掺入并且与蛋白质中的天然侧链几乎没有相似之处。从容易获得的2,2,6,6-四甲基-4-哌啶酮开始，描述了三种自旋标记的1-氨基酸的对映选择性合成。这些SLAA可以更好地复制蛋白质中的规范残基，并旨在通过遗传掺入或固相肽合成进行生物学掺入。
• Rational Design and Synthesis of Modified Teixobactin Analogues: In Vitro Antibacterial Activity against <i>Staphylococcus aureus</i> , <i>Propionibacterium acnes</i> and <i>Pseudomonas aeruginosa</i>
  作者：Vivian Ng、Sarah A. Kuehne、Weng C. Chan

  DOI：10.1002/chem.201801423

  日期：2018.6.26

  Extensive antimicrobial susceptibility assessment against a panel of clinically relevant Staphylococcus aureus and Propionibacterium acnes strains led to the identification of the new lead compound, [Arg(Me)10,Nle11]teixobactin, with an excellent bactericidal activity (minimum inhibitory concentration (MIC)=2–4 μg mL−1). Significantly, the antimicrobial activity of several of the teixobactin analogues against

  Teixobactin是最近发现的一种与细菌脂质II和脂质III结合的二肽肽，为设计新的抗菌剂提供了有希望的分子支架。在这里，我们描述了系统修饰的teixobactin类似物的合成和抗菌评估。Ile 11残基被脂肪族等聚体取代，修饰残基10的胍基基团，以及向大环引入刚性化残基（即脱氢氨基酸），产生了有用的结构活性信息。针对一组临床相关的金黄色葡萄球菌和痤疮丙酸杆菌菌株进行了广泛的药敏评估，从而鉴定出了新的先导化合物[Arg（Me）10，Nle 11 ] teixobactin，具有优异的杀菌活性（最低抑菌浓度（MIC）= 2-4μgmL -1）。值得注意的是，当与亚MIC浓度的外膜破坏性抗生素大肠菌素结合使用时，“ teixobactin类似物”对致病性革兰氏阴性铜绿假单胞菌的抗微生物活性被“恢复”。[Tfn 10，Nle 11 ] teixobactin（32μgmL -1）-colistin（2μgmL
• [EN] NOVEL CYCLIC BORONATE INHIBITORS OF HCV REPLICATION<br/>[FR] NOUVEAUX INHIBITEURS DE BORONATE CYCLIQUES DE RÉPLICATION DU VIRUS DE L'HÉPATITE C
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2009046098A1

  公开（公告）日：2009-04-09

  Compounds of formula (I) or a salt thereof are provided; wherein R1, R2, R3, R4, R6, R8, R20, R30, Y, Z and n are as defined in the description. Uses of the compounds as medicaments, and in the manufacture of medicaments for treating viral infection, especially HCV infection are also disclosed. The invention further comprises processes to make these compounds and pharmaceutical formulations thereof.

  提供了化学式（I）的化合物或其盐；其中R1、R2、R3、R4、R6、R8、R20、R30、Y、Z和n的定义如描述中所述。还公开了将这些化合物用作药物以及用于治疗病毒感染，特别是HCV感染的药物制造中的用途。该发明还包括制备这些化合物和其药物配方的过程。
• Synthesis, Ni(II) Schiff base complexation and structural analysis of fluorinated analogs of the ligand (S)-2-[N-(N′-benzylprolyl)amino]benzophenone (BPB)
  作者：Natalie J. Tatum、Dmitry S. Yufit、Steven L. Cobb、Christopher R. Coxon

  DOI：10.1016/j.jfluchem.2015.02.007

  日期：2015.5

  first X-ray crystal structure of the well-known (S)-l-ala-Ni-BPB complex (1) and compare this with the X-ray crystal structures obtained for two novel fluorinated (S)-l-ala-Ni-BPB complexes (8 and 12) that contain either an S- or R-fluorine atom on the proline ring of the BPB ligand. The preparation of complexes 8 and 12 has been enabled by the synthesis of two new fluorinated BPB ligands (7 and 11)

  本文我们报告的公知的（的第一X射线晶体结构小号） -升-Ala-Ni类复合BPB（1）中，用了两个新获得的X射线晶体结构比较这氟化（小号） -升-ala-Ni-BPB配合物（8和12），其在BPB配体的脯氨酸环上包含S-或R-氟原子。通过合成两个新的氟化BPB配体（7和11）可以制备配合物8和12）。在这项工作中，我们希望观察引入单个氟原子对已知配合物1的结构影响。由此，我们强调了一种新颖的氟-镍相互作用，它在DFT计算的基础上似乎为所制备的一种配合物（（S）-1-丙氨酸-Ni-BPB配合物8）提供了额外的稳定性。
• Synthesis of enantio- and diastereo-isomerically pure β- and γ-substituted glutamic acids via glycine condensation with activated olefins
  作者：Yuri N. Belokon、Aleksandr G. Bulychev、Mikhail G. Ryzhov、Sergei V. Vitt、Andrei S. Batsanov、Yuri T. Struchkov、Vladimir I. Bakhmutov、Vasili M. Belikov

  DOI：10.1039/p19860001865

  日期：——

  The glycine fragment in the nickel(II) complex formed from the Schiff base of glycine and (S)-o[(N-benzylprolyl)amino]benzophenone undergoes base-catalysed Michael addition in methanol in the presence of MeONa to the activated olefins methyl acrylate, acrylonitrile, methyl methacrylate, acrolein, and methyl trans-cinnamate. Complexes of substituted (S)-glutamic acid or its derivatives were formed in

  由甘氨酸的席夫碱和（S）-o [（N-苄基脯氨酰基）氨基]二苯甲酮形成的镍（II）配合物中的甘氨酸片段在MeONa存在下在甲醇中经历碱催化的迈克尔加成反应生成活化的烯烃甲基丙烯酸酯，丙烯腈，甲基丙烯酸甲酯，丙烯醛和反肉桂酸甲酯。取代的（S谷氨酸或其衍生物以良好的化学产率形成，并且在氨基酸部分的α-碳原子上几乎完全非对映异构。β-和γ-原子的非对映选择性不明显，但同分异构体配合物可通过色谱法轻松分离。用HCl水溶液裂解纯的非对映异构体，以良好的收率得到光学纯的谷氨酸，并再生了原始的手性试剂。通过1 H nmr光谱和相应原始配合物的晶体结构X射线分析，确定了氨基酸β-和γ-碳原子的构型。由三乙胺在甲醇中催化而向丙烯醛中添加，将仅生成1,4-加合物。由此获得的氨基酸可以转化为（S）-脯氨酸通过用NaBH 4还原。