(2-氧代-2-苯乙基)-氨基甲酸叔丁酯 | 76477-26-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2-氧代-2-苯乙基)-氨基甲酸叔丁酯
• 英文名称: tert-butyl (2-oxo-2-phenylethyl)carbamate
• 英文别名: 2-[N-(tert-butoxycarbonyl)amino]acetophenone；(2-Oxo-2-phenylethyl)carbamic acid tert-butyl ester；tert-butyl N-phenacylcarbamate
• CAS: 76477-26-4
• 化学式: C₁₃H₁₇NO₃
• mdl: MFCD08692497
• 分子量: 235.283
• InChiKey: ODIKTWMCZYPCKQ-UHFFFAOYSA-N

物化性质

• 熔点：
  56 °C
• 沸点：
  371.7±25.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(N-BOC-Amino)acetophenone
Synonyms: tert-Butyl N-(2-oxo-2-phenylethyl)carbamate

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 2-(N-BOC-Amino)acetophenone
CAS number: 76477-26-4

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C13H17NO3
Molecular weight: 235.3

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (2-氧代-2-苯乙基)-氨基甲酸叔丁酯 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 N-(2-hydroxy-2-phenylethyl)pent-4-ynamide
  参考文献：
  名称：

  自组装用于癌症化疗的氧化反应性聚乙二醇-紫杉醇前药。

  摘要：

  两亲性药物偶联物可以自组装成纳米载体用于癌症药物递送，但是关键是设计稳定但细胞内不稳定的药物接头，以在血液循环中保留药物但快速地释放细胞内药物。紫杉醇（PTX）的缀合通常是通过其2'-羟基的酯进行的，但该酯要么太稳定以至于无法在细胞质中释放PTX，要么不稳定，在循环过程中会水解。本文中，我们报道了一种基于对-（硼酸酯）苄基的肿瘤特异性可裂解的连接子，用于制备与聚乙二醇（PEG，Mw = 5000 Da）（PEG-B-PTX）的PTX-缀合物。两亲性PEG-B-PTX自组装成胶束，平均尺寸约为50 nm，PTX负载量为13.3 wt％。PEG-B-PTX胶束在正常生理环境下非常稳定，因此在血液腔中循环很长，但是由于肿瘤中活性氧（ROS）水平升高，其PTX迅速解离并释放。与临床使用的紫杉醇相比，缀合物胶束在体外和体内显示出显着提高的抗人神经胶质瘤和乳腺癌细胞的抗肿瘤效率，并降低了毒性。因此，P

  DOI：

  10.1016/j.jconrel.2020.02.038
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 重铬酸吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2-氧代-2-苯乙基)-氨基甲酸叔丁酯
  参考文献：
  名称：

  Enantioselective synthesis of β-hydroxy amines and aziridines using asymmetric transfer hydrogenation of α-amino ketones

  摘要：

  α-氨基酮的对映选择性转移氢化是一种有效的方法，用于手性合成β-羟基胺和氮丙啶。

  DOI：

  10.1039/b102895m

文献信息

• Pd-Catalyzed Decarboxylative Olefination: Stereoselective Synthesis of Polysubstituted Butadienes and Macrocyclic P-glycoprotein Inhibitors
  作者：Bichao Song、Peipei Xie、Yingzi Li、Jiping Hao、Lu Wang、Xiangyang Chen、Zhongliang Xu、Haitian Quan、Liguang Lou、Yuanzhi Xia、K. N. Houk、Weibo Yang

  DOI：10.1021/jacs.0c00078

  日期：2020.6.3

  The efficient and stereoselective synthesis of polysubstituted butadienes, especially the multifunctional butadiene, represents a great challenge in organic synthesis. Herein, we wish to report a distinctive Pd(0) car-bene-initiated decarboxylative olefination approach that enables the direct coupling of diazo esters with vinylethylene carbonates (VECs), vinyl oxazolidinones, or vinyl benzoxazinones

  多取代丁二烯尤其是多功能丁二烯的高效立体选择性合成是有机合成中的一大挑战。在此，我们希望报告一种独特的 Pd(0) 碳烯引发的脱羧烯化方法，该方法能够将重氮酯与乙烯基碳酸亚乙酯 (VEC)、乙烯基恶唑烷酮或乙烯基苯并恶嗪酮直接偶联，以提供醇、胺或苯胺。含有 1,3-二烯，产率中等至高，具有出色的立体选择性。该协议具有操作简单、反应条件温和、底物范围广泛和可扩展性等特点。值得注意的是，分离并表征了一种结构独特的烯丙基 Pd(II) 中间体。DFT 计算和控制实验表明，稀有的 Pd(0) 卡宾中间体可能参与该反应。此外，作为新型构件的多取代丁二烯前所未有地组装成大环化合物，有效抑制了 P-糖蛋白 (P-gp)，并以 190 倍的速度显着逆转了癌细胞的多药耐药性。
• Organic metal compound and process for preparing optically-active alcohols using the same
  申请人：Miki Takashi

  公开号：US20090062573A1

  公开（公告）日：2009-03-05

  The present invention provides an asymmetric reduction catalyst effective in preparing optically-active alcohol compounds having various functional groups, and a process for preparing optically-active alcohol compounds using said asymmetric reduction catalyst. The organic metal compound of the present invention is represented by the following general formula (1): wherein R 1 and R 2 may be mutually identical or different, and are an alkyl group, a phenyl group, a naphthyl group, a cycloalkyl group, or an alicyclic ring formed by binding R 1 and R 2 , which may have a substituent; R 3 is a hydrogen atom or an alkyl group; Cp is a cyclopentadienyl group, which may have a substituent, bound to M 1 via a π bond; X 1 is a halogen atom or a hydrido group; M 1 is rhodium or iridium; and * denotes asymmetric carbon.

  本发明提供了一种在制备具有各种官能团的光学活性醇化合物中有效的非对称还原催化剂，以及使用所述非对称还原催化剂制备光学活性醇化合物的方法。 本发明的有机金属化合物由以下通式(1)表示： 其中R1和R2可以相互相同或不同，并且是烷基、苯基、萘基、环烷基或由R1和R2结合形成的脂肪环环，其中可能含有取代基；R3是氢原子或烷基；Cp是环戊二烯基，可能含有取代基，通过π键与M1结合；X1是卤素原子或氢化物基团；M1是铑或铱；*表示不对称碳。
• β-唑类-苯基酮衍生物及其用途
  申请人：沈阳药科大学

  公开号：CN109485607B

  公开（公告）日：2020-11-17

  本发明属于药物合成技术领域，提供了如通式所示的β‑唑类‑苯基酮衍生物及其立体异构体或其药学上可接受的盐、水合物、溶剂化物或前药和它们的制备方法，其中A、B、R1、R2、R3、X具有在说明书中给出的定义。本发明所提供的化合物对浅表和深部真菌具有较强的抑制活性，与临床上使用的抗真菌药物相比，具有活性高、毒性低、抗菌谱广等优点，可用于制备抗真菌药物。
• Improving the metabolic stability of antifungal compounds based on a scaffold hopping strategy: Design, synthesis, and structure-activity relationship studies of dihydrooxazole derivatives
  作者：Liyu Zhao、Wenbo Yin、Yin Sun、Nannan Sun、Linfeng Tian、Yang Zheng、Chu Zhang、Shizhen Zhao、Xin Su、Dongmei Zhao、Maosheng Cheng

  DOI：10.1016/j.ejmech.2021.113715

  日期：2021.11

  l-amino alcohol derivatives exhibited high antifungal activity, but the metabolic stability of human liver microsomes in vitro was poor, and the half-life of optimal compound 5 was less than 5 min. To improve the metabolic properties of the compounds, the scaffold hopping strategy was adopted and a series of antifungal compounds with a dihydrooxazole scaffold was designed and synthesized. Compounds

  l-氨基醇衍生物具有较高的抗真菌活性，但人肝微粒体体外代谢稳定性较差，最佳化合物5的半衰期小于5 min。为改善化合物的代谢特性，采用支架跳跃策略，设计合成了一系列具有二氢恶唑支架的抗真菌化合物。二氢恶唑环上被4-苯基取代的化合物A33-A38对白色念珠菌、热带念珠菌和克氏念珠菌表现出优异的抗真菌活性，MIC值在0.03~0.25  μ之间。克/毫升。此外，化合物A33和A34在体外人肝微粒体中的代谢稳定性显着提高，半衰期分别大于145 min和59.1 min。此外，SD大鼠的药代动力学研究表明，A33具有良好的药代动力学特性，生物利用度为77.69%，半衰期（静脉给药）为9.35 h，表明A33值得进一步研究。
• Combating fluconazole-resistant fungi with novel β-azole-phenylacetone derivatives
  作者：Liyu Zhao、Nannan Sun、Linfeng Tian、Yin Sun、Yixuan Chen、Xinran Wang、Shizhen Zhao、Xin Su、Dongmei Zhao、Maosheng Cheng

  DOI：10.1016/j.ejmech.2019.111689

  日期：2019.12

  excellent antifungal activities against five pathogenic strains with MIC values in the range of 0.03-1 μg/mL. Compounds with R1 = 3-F substituted and 15o and 15ae exhibited moderate antifungal activities against fluconazole-resistant strains 17# and CaR with MIC values in the range of 1-8 μg/mL. Compounds with R1 = H or 2-F (such as 15a, 15o, 15p) displayed moderate to good antifungal activity against

  设计并合成了一系列具有新颖结构的β-唑-苯丙酮衍生物，以抵抗易感真菌感染和耐药真菌感染的增加。评估了合成化合物对五种敏感菌株和五种耐氟康唑的菌株的抗真菌活性。抗真菌活性测试表明，大多数化合物对5种病原菌株均表现出优异的抗真菌活性，其MIC值在0.03-1μg/ mL的范围内。R1 = 3-F取代且15o和15ae的化合物对MIC范围为1-8μg/ mL的耐氟康唑耐药菌株17＃和CaR表现出中等的抗真菌活性。R1 = H或2-F（例如15a，15o，15p）的化合物对耐氟康唑的菌株632具有中等至良好的抗真菌活性，901和904的MIC值在0.125-4μg/ mL的范围内。值得注意的是，15o和15ae对五种敏感菌株和五种对氟康唑耐药的菌株均表现出抗真菌活性。初步的机理研究表明，化合物15ae的有效抗真菌活性源于对白色念珠菌CYP51的抑制作用。化合物15o，15z和15ae对哺乳动物A549细胞几乎无毒。