4-氯-N-[苄氧羰基]-DL-苯丙氨酸 | 55478-54-1

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苯丙氨酸类衍生物
• 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
• 中文名称: 4-氯-N-[苄氧羰基]-DL-苯丙氨酸
• 中文别名: 苄氧羰基-DL-4-氯-苯丙氨酸
• 英文名称: Z-DL-Phe(4Cl)
• 英文别名: Z-Phe(4Cl)-OH；N-Cbz-DL-4-chlorophenylalanine；N-benzyloxycarbonyl-D-para-chlorophenylalanine；N-Phenoxycarbonyl-DL-p-chlor-phenylalanin；Z-DL-Phe(4-CL)-OH；3-(4-chlorophenyl)-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 55478-54-1
• 化学式: C₁₇H₁₆ClNO₄
• mdl: MFCD00191079
• 分子量: 333.771
• InChiKey: LEWUPPXPENCAKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.176
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Z-DL-Phe(4-Cl)-OH
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: Z-DL-Phe(4-Cl)-OH
CAS number: 55478-54-1

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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: C17H16ClNO4
Molecular weight: 333.8

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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, hydrogen chloride.

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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：

  4-氯-N-[苄氧羰基]-DL-苯丙氨酸 在 potassium phosphate 、 氯化镍二甲氧基乙烷 、 二碳酸二叔丁酯 、 4,4'-二叔丁基-2,2'-二吡啶 、 2-甲基-2-丙基1-[(2-甲基-2-丙基)氧基]-2(1H)-异喹啉羧酸酯 作用下， 以 二氯甲烷 为溶剂， 反应 96.67h， 生成
  参考文献：
  名称：

  通过氯自由基的光催化生成，使芳基氯化物发生温和的氧化还原中性甲酰化反应

  摘要：

  我们报告了芳基氯化物的氧化还原中性甲酰化反应，该反应是通过镍和光氧化还原催化作用对1,3-二氧戊环进行选择性2官能化而进行的。这种可扩展的台式方法相对于传统的还原羰基化具有明显的优势，因为它不使用一氧化碳，加压气体或化学计量的还原剂。温和的条件为丰富而复杂的芳基氯原料提供了空前的应用范围。

  DOI：

  10.1002/anie.201702079
• 作为产物：
  描述：

  Caesium; 2-benzyloxycarbonylamino-3-(4-chloro-phenyl)-propionate 在 α-chymotrypsin immobilised on Celite 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.0h， 生成 4-氯-N-[苄氧羰基]-DL-苯丙氨酸
  参考文献：
  名称：

  Superiority of the carbamoylmethyl ester as an acyl donor for the kinetically controlled amide-bond formation mediated by α-chymotrypsinElectronic supplementary information (ESI) available: elemental analyses and HPLC separation data. See http://www.rsc.org/suppdata/p1/b1/b108735p/

  摘要：

  研究表明，羰甲基氨基甲酸酯作为酰基供体在α-糜蛋白酶催化的动力学控制的肽键形成反应中具有优越性，这体现在天然不良氨基酸底物Ala与各种氨基酸残基作为氨基组分的偶联反应中，以及与非蛋白氨基酸如卤代苯丙氨酸作为羧基组分的偶联反应中。此外，这种方法还应用于氨基酸残基与手性胺之间的酰胺键形成反应，具有高度立体选择性。

  DOI：

  10.1039/b108735p

文献信息

• α-Chymotrypsin-catalysed peptide synthesis via the kinetically controlled approach using activated esters as acyl donors in organic solvents with low water content: incorporation of non-protein amino acids into peptides
  作者：Toshifumi Miyazawa、Shin’ichi Nakajo、Miyako Nishikawa、Kazumi Hamahara、Kiwamu Imagawa、Eiichi Ensatsu、Ryoji Yanagihara、Takashi Yamada

  DOI：10.1039/b004183l

  日期：——

  α-chymotrypsin-catalysed peptide synthesis via the kinetically controlled approach is greatly improved by the use of activated esters such as the 2,2,2-trifluoroethyl ester as acyl donors instead of the conventional methyl ester in organic solvents such as acetonitrile with low water content. This approach is useful for the incorporation of non-protein amino acids such as halogenophenylalanines into peptides.

  在α-胰凝乳蛋白酶催化下的偶联效率 肽通过使用活化的方法，通过动力学控制方法的合成得到了极大的改善酯类 例如2,2,2-三氟乙基酯 酰基供体 代替传统的有机甲酯 溶剂 如 乙腈 低 水内容。这种方法对于合并非蛋白质 氨基酸 如卤代苯丙氨酸成 肽。
• 2-Piperazinone compounds and their use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0643072A1

  公开（公告）日：1995-03-15

  Compounds of the formula [wherein A represents amidino group or an optionally substituted aminoethyl; R¹⁰ represents one species selected from a group consisting of nitro group, a halogen atom, a lower alkenyl group, a lower alkynyl group, a lower alkyloxycarbonyl group and a group represented by the formula OR¹¹ (wherein R¹¹ is hydrogen atom or a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkanoyl group, a carbamoyl group or a methanesulfonyl group, each of which may be substituted; R¹² and R¹³ respectively represent hydrogen atom, hydroxyl group, a lower alkoxy group or a halogen atom; X represents hydroxyl group, p-hydroxyphenyl group or an optionally esterified or amidated carboxyl group; Y represents an optionally esterified or amidated carboxyl group; and n denotes 1 or 2], or a salt thereof and agent for inhibiting adhesion of cells, which comprise said compound, and these have more potent and long lasting activities of inhibiting cell-adhesion, thus being useful as an orally administrable anti-thrombotic agent.

  式中的化合物 [其中 A 代表脒基或任选取代的氨基乙基；R¹⁰ 代表一种选自硝基、卤素原子、低级烯基、低级炔基、低级烷氧羰基和式 OR¹¹ 所代表的基团（其中 R¹¹ 为氢原子或低级烷基、低级烯基、低级炔基、低级烷酰基、氨基甲酰基或甲磺酰基，每个基团均可被取代；R¹² 和 R¹³ 分别代表氢原子、羟基、低级烷氧基或卤原子；X 代表羟基、对羟基苯基或任选酯化或酰胺化的羧基；Y 代表任选酯化或酰胺化的羧基；和 n 表示 1 或 2]，或其盐和抑制细胞粘附的制剂，其中包括所述化合物，这些化合物具有更强和更持久的抑制细胞粘附的活性，因此可用作口服抗血栓形成剂。
• Kametani, Tetsuji; Kigasawa, Kazuo; Hiiragi, Mineharu, Heterocycles, 1981, vol. 16, # 7, p. 1205 - 1242
  作者：Kametani, Tetsuji、Kigasawa, Kazuo、Hiiragi, Mineharu、Wakisaka, Kikuo、Haga, Seiji、et al.

  DOI：——

  日期：——
• α-Chymotrypsin-catalysed peptide synthesis using activated esters as acyl donors
  作者：Toshifumi Miyazawa、Shin'ichi Nakajo、Miyako Nishikawa、Kiwamu Imagawa、Ryoji Yanagihara、Takashi Yamada

  DOI：10.1039/p19960002867

  日期：——

  The coupling efficiency in alpha-chymotrypsin-catalysed peptide synthesis is greatly improved by the use of activated esters such as the 2,2,2-trifluoroethyl ester as acyl donor instead of the conventional methyl ester; this approach Is useful for the incorporation of non-protein amino acids into peptides.
• Kametani, Tetsuji; Suzuki, Yukio; Kigasawa, Kazuo, Heterocycles, 1982, vol. 18, p. 295 - 319
  作者：Kametani, Tetsuji、Suzuki, Yukio、Kigasawa, Kazuo、Hiiragi, Mineharu、Wakisaka, Kikuo、et al.

  DOI：——

  日期：——