N-acetylphenylalanine methyl ester | 21156-62-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-acetylphenylalanine methyl ester
• 英文别名: methyl 2-acetamido-3-phenylpropanoate；N-acetyl-(RS)-phenylalanine methyl ester；methyl (+/-)-2-acetylamino-3-phenylpropanoate；Methyl N-acetyl-DL-phenylalaninate
• CAS: 21156-62-7；62436-70-8；3618-96-0
• 化学式: C₁₂H₁₅NO₃
• mdl: MFCD00066059
• 分子量: 221.256
• InChiKey: IKGHIFGXPVLPFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 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
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：室温、干燥密封

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ac-phe-ome
Synonyms:

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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: Ac-phe-ome
CAS number: 3618-96-0

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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.
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: C12H15NO3
Molecular weight: 221.3

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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

制备方法与用途

乙酰-D-苯丙氨酸甲酯是一种苯丙氨酸衍生物。

反应信息

• 作为反应物：
  描述：

  N-acetylphenylalanine methyl ester 在 cross-linked yeast cells (Saccharomyces cerevisiae) 、 水 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 生成 N-乙酰-L-苯丙氨酸
  参考文献：
  名称：

  Reverse micelles, an alternative to aqueous medium for microbial reactions: yeast mediated resolution of .alpha.-amino acids in reverse micelles

  摘要：

  DOI：

  10.1021/jo00274a052
• 作为产物：
  描述：

  DL-苯丙氨酸 在 碳酸氢钠 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 水 为溶剂， 生成 N-acetylphenylalanine methyl ester
  参考文献：
  名称：

  常规和准确的nmr测定α-氨基酸和α-氨基酸衍生物的对映体纯度

  摘要：

  作为N-乙酰基衍生物的α-氨基酸，α-氨基酯和α-氨基内酯的衍生化可以对对映体纯度进行准确的NMR测定。在这些条件下，具有手性移位试剂的主要配位点将对应于NMR观察位点。确定导致最高ΔΔδ值的实验因素。无法建立与绝对配置的直接关联。

  DOI：

  10.1016/s0040-4020(01)86812-5
• 作为试剂：
  描述：

  sodium hydroxide 、 N-acetylphenylalanine methyl ester 、 、 在 L-苯丙氨酸 、 3-庚酮 、 N-acetylphenylalanine methyl ester 作用下， 以 3-庚酮 为溶剂， 反应 12.0h， 生成 L-苯丙氨酸
  参考文献：
  名称：

  Method of producing L-phenylalanine

  摘要：

  提供了一种高光学纯度生产L-苯丙氨酸的方法，其包括在水的存在下，使用能够水解L-型N-酰基苯丙氨酸烷基酯的酶处理L-型N-酰基苯丙氨酸烷基酯，以得到L-苯丙氨酸。

  公开号：

  US04743547A1

文献信息

• Two Stereoinduction Events in One C−H Activation Step: A Route towards Terphenyl Ligands with Two Atropisomeric Axes
  作者：Quentin Dherbassy、Jean‐Pierre Djukic、Joanna Wencel‐Delord、Françoise Colobert

  DOI：10.1002/anie.201801130

  日期：2018.4.16

  scaffolds—ortho‐orientated terphenyls presenting two atropisomeric Ar–Ar axes. These unusual structures were built up by using the C−H activation approach, and remarkably, both chiral axes were controlled with excellent stereoselectivity in a single transformation. During the reaction, not only does atroposelective functionalization of a biaryl precursor occur to establish one stereogenic axis, but an

  在这里，我们公开了原始手性支架的合成-呈现两个阻转异构Ar-Ar轴的邻位三联苯。这些不寻常的结构是通过使用CH活化方法建立的，并且值得注意的是，两个手性轴在一次转化中都具有出色的立体选择性。在反应过程中，不仅会发生联芳基前体的对映选择性官能化以建立一个立体轴，而且还会发生空前的对映立体选择性CH芳基化反应，从而生成第二个立体成因元素。这些对映体纯的邻位叔苯基具有原始的三维结构，因此为建立对映体纯的双齿配体（例如新的配体S / N-Biax和二膦酸BiaxPhos）库提供了独特的基础。
• N-carbamoyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidines(CAPP). Efficient new chiral ligands for asymmetric hydrogenation
  作者：Iwao Ojima、Noriko Yoda

  DOI：10.1016/s0040-4039(00)78836-8

  日期：1980.1

  N-(N′-substituted carbamoyl)-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidines (CAPP) was prepared, which exhibited excellent stereoselectivity in the asymmetric hydrogenation of α-acetamidocinnamic acid derivatives and itaconic acid as chiral ligand of the rhodium(I) catalyst.

  制备了一系列的N-（N'-取代的氨基甲酰基）-4-二苯基膦基-2-二苯基膦基甲基吡咯烷酮（CAPP），它们在作为铑的手性配体的α-乙酰氨基doc酰胺酸衍生物和衣康酸的不对称加氢中表现出优异的立体选择性。 I）催化剂。
• Complementary Site-Selective Sulfonylation of Aromatic Amines by Superacid Activation
  作者：Paul Bourbon、Emeline Appert、Agnès Martin-Mingot、Bastien Michelet、Sébastien Thibaudeau

  DOI：10.1021/acs.orglett.1c00994

  日期：2021.6.4

  superacidic conditions, aniline and indole derivatives are sulfonylated at low temperature with easy-to-access arenesulfonic acids or arenesulfonyl hydrazides. By modification of the functional-group directing effect through protonation, this method allows nonclassical site functionalization by overcoming the innate regioselectivity of electrophilic aromatic substitution. This superacid-mediated sulfonylation

  在超酸性条件下，苯胺和吲哚衍生物在低温下用易于获得的芳烃磺酸或芳烃磺酰肼进行磺酰化。通过质子化修饰官能团导向效应，该方法通过克服亲电芳香取代的先天区域选择性，允许非经典位点官能化。这种超强酸介导的芳烃磺酰化是对现有方法的补充，可以通过质子化保护应用于天然生物碱和活性药物成分的后期位点选择性功能化。
• Oral drug delivery compositions and methods
  申请人：Emisphere Technologies, Inc.

  公开号：US05766633A1

  公开（公告）日：1998-06-16

  The present invention relates to an oral drug delivery system, and in particular to modified amino acids and modified amino acid derivatives for use as a delivery system of sensitive agents such as bioactive peptides. The modified amino acids and derivatives can form non-covalent mixtures with active biological agents and in an alternate embodiment can releasably carry active agents. Modified amino acids can also form drug containing microspheres. These mixtures are suitable for oral administration of biologically active agents to animals. Methods for the preparation of such amino acids are also disclosed.

  本发明涉及口服药物输送系统，特别是用作敏感剂（如生物活性肽）输送系统的改性氨基酸和改性氨基酸衍生物。这些改性氨基酸和衍生物可以与活性生物制剂形成非共价混合物，并在另一实施例中可以可释放地携带活性剂。改性氨基酸还可以形成含药微球。这些混合物适用于将生物活性剂口服给动物。还公开了制备这种氨基酸的方法。
• Imidazole derivatives having anti-HIV activity
  申请人：Shionogi & Co., Ltd.

  公开号：US05326780A1

  公开（公告）日：1994-07-05

  A novel imidazole derivatives of formula I: ##STR1## wherein R.sup.1 is hydrogen, alkyl, halogen, or optionally substituted aryl; R.sup.2 is alkyl, optionally substituted aryl optionally substituted aralkyl, or optionally substituted hetero ring group; R.sup.3 is hydrogen, alkyl, optionally substituted aryl, optionally substituted aralkyl, or optionally substituted hydroxyalkyl; R.sup.4 is hydrogen, alkyl, halogen, acyl, optionally substituted hydroxyalkyl, optionally esterified or amidated carboxyl group, hydroxy group, aryl or arylthio; X is S, SO, SO.sub.2, CH.sub.2, or Se; n is an integer of 1 to 3, or a pharmaceutically acceptable salt thereof, said derivative having anti-HIV activity and being useful for the treatment of HIV infections.

  一种新型咪唑衍生物，化学式如下：##STR1## 其中R.sup.1为氢、烷基、卤素，或可选择性取代的芳基；R.sup.2为烷基、可选择性取代的芳基、可选择性取代的芳基烷基，或可选择性取代的杂环基团；R.sup.3为氢、烷基、可选择性取代的芳基、可选择性取代的芳基烷基，或可选择性取代的羟基烷基；R.sup.4为氢、烷基、卤素、酰基、可选择性取代的羟基烷基、可酯化或酰胺化的羧基、羟基、芳基或芳硫基；X为S、SO、SO.sub.2、CH.sub.2或Se；n为1至3的整数，或其药学上可接受的盐，该衍生物具有抗HIV活性，并可用于治疗HIV感染。