D-苯丙氨酸叔丁酯盐酸盐 | 3403-25-6

• 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: D-苯丙氨酸叔丁酯盐酸盐
• 中文别名: D-(+)-对甲基二苯甲酰酒石酸；H-D-Phe-OtBu.HCl
• 英文名称: D-phenylalanine tert-butyl ester hydrochloride
• 英文别名: tert-butyl (2R)-2-amino-3-phenyl-propanoate hydrochloride；(R)-tert-Butyl 2-amino-3-phenylpropanoate hydrochloride；tert-butyl (2R)-2-amino-3-phenylpropanoate;hydrochloride
• CAS: 3403-25-6
• 化学式: C₁₃H₁₉NO₂*ClH
• mdl: MFCD00153455
• 分子量: 257.76
• InChiKey: FDMCEXDXULPJPG-RFVHGSKJSA-N

物化性质

• 熔点：
  208-211℃
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R36
• 海关编码：
  2922499990
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  0-6°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
H-D-Phe-OtBu HCl
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H319: Causes serious eye irritation
H412: Harmful to aquatic life with long lasting effects
P273: Avoid release to the environment
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: H-D-Phe-OtBu HCl
CAS number: 3403-25-6

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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
This product should be handled only by, or under the close supervision of, those properly qualified
Handling:
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.
Storage: Store in closed vessels.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C13H19NO2.ClH
Molecular weight: 257.8

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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

制备方法与用途

H-D-Phe-OtBu·HCl是一种苯丙氨酸衍生物。

反应信息

• 作为反应物：
  描述：

  D-苯丙氨酸叔丁酯盐酸盐 在 劳森试剂 、 盐酸 、 TEA 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 Z-L-Leu-D-Phe-OH
  参考文献：
  名称：

  氨基酸和肽的研究x：Hplc介导的2,4-双（4-甲氧基苯基）-1,3,2,4-二硫代二磷-苯丙氨酸2,4-二硫化物（劳氏试剂）的无消旋偶联试剂

  摘要：

  已经测试了易于获得的2,4-双（4-甲氧基苯基）-1,3,2,4-二硫代二膦2,4-二硫化物（Lawesson's Reagent）1作为肽合成中外消旋的偶联剂。测定步骤是通过HPLC分离立体异构产物。ZS-Pro-S-Val-S-Pro-OtBu和ZS-Leu-S-Phe-S-Val-OtBu被用作2 + 1段偶联的测试肽，并且只有少量差向异构（0.5和分别观察到<0.1％）。

  DOI：

  10.1016/s0040-4020(01)91366-3
• 作为产物：
  描述：

  D-苯丙氨酸 、 异丁烯 在 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 以77%的产率得到D-苯丙氨酸叔丁酯盐酸盐
  参考文献：
  名称：

  氨基酸和肽的研究x：Hplc介导的2,4-双（4-甲氧基苯基）-1,3,2,4-二硫代二磷-苯丙氨酸2,4-二硫化物（劳氏试剂）的无消旋偶联试剂

  摘要：

  已经测试了易于获得的2,4-双（4-甲氧基苯基）-1,3,2,4-二硫代二膦2,4-二硫化物（Lawesson's Reagent）1作为肽合成中外消旋的偶联剂。测定步骤是通过HPLC分离立体异构产物。ZS-Pro-S-Val-S-Pro-OtBu和ZS-Leu-S-Phe-S-Val-OtBu被用作2 + 1段偶联的测试肽，并且只有少量差向异构（0.5和分别观察到<0.1％）。

  DOI：

  10.1016/s0040-4020(01)91366-3

文献信息

• Macrocyclic Modulators of the Ghrelin Receptor
  申请人：Ocera Therapeutics, Inc.

  公开号：US20180110824A1

  公开（公告）日：2018-04-26

  The present invention provides novel conformationally-defined macrocyclic compounds that have been demonstrated to be selective modulators of the ghrelin receptor (growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, gastrointestinal disorders, cardiovascular disorders, obesity and obesity-associated disorders, central nervous system disorders, genetic disorders, hyperproliferative disorders and inflammatory disorders.

  本发明提供了一种新颖的构象定义明确的大环化合物，已经证明是生长激素分泌素受体（GHS-R1a及其亚型、异构体和变体）的选择性调节剂。本文还描述了合成这些新型化合物的方法。这些化合物可用作生长激素分泌素受体的激动剂，用于治疗和预防一系列医疗状况，包括但不限于代谢和/或内分泌紊乱、胃肠道紊乱、心血管疾病、肥胖和与肥胖相关的疾病、中枢神经系统疾病、遗传疾病、过度增殖性疾病和炎症性疾病。
• [EN] DIPHENYLAZETIDINONE DERIVATES PROCESSING CHOLESTEROL ABSORPTION INHIBITORY ACTIVITY<br/>[FR] DERIVES DIPHENYLAZETIDINONE PRESENTANT UNE ACTIVITE D'INHIBITION D'ABSORPTION DU CHOLESTEROL
  申请人：ASTRAZENECA AB

  公开号：WO2005061451A1

  公开（公告）日：2005-07-07

  Compounds of formula (XV): [Chemical formula should be inserted here. Please see paper copy] (XV) (wherein variable groups are as defined within) pharmaceutically acceptable salts, solvates, solvates of such salts and prodrugs thereof and their use as cholesterol absorption inhibitors for the treatment of hyperlipidaemia are described. Processes for their manufacture and pharmaceutical compositions containing them are also described.

  公式（XV）的化合物：[应在此处插入化学公式。请参见纸质副本]（XV）（其中变量组如内部定义）药物可接受的盐、溶剂化物、这些盐的溶剂化物和前药及其用作治疗高脂血症的胆固醇吸收抑制剂。还描述了它们的制造过程和含有它们的药物组合物。
• Solid-Phase Synthesis of Oxetane Modified Peptides
  作者：Jonathan D. Beadle、Astrid Knuhtsen、Alex Hoose、Piotr Raubo、Andrew G. Jamieson、Michael Shipman

  DOI：10.1021/acs.orglett.7b01466

  日期：2017.6.16

  Solid-phase peptide synthesis (SPPS) is used to create peptidomimetics in which one of the backbone amide C═O bonds is replaced by a four-membered oxetane ring. The oxetane containing dipeptide building blocks are made in three steps in solution, then integrated into peptide chains by conventional Fmoc SPPS. This methodology is used to make a range of peptides in high purity including backbone modified

  固相肽合成（SPPS）用于创建拟肽，其中主链酰胺C═O键之一被四元氧杂环丁烷环取代。含氧杂环丁烷的二肽结构单元可在溶液中分三步制备，然后通过常规的Fmoc SPPS整合到肽链中。该方法用于制备一系列高纯度的肽，包括九肽缓激肽的主链修饰衍生物以及Met-和Leu-脑啡肽。
• Chiral Arylated Amines via C−N Coupling of Chiral Amines with Aryl Bromides Promoted by Light
  作者：Geyang Song、Liu Yang、Jing‐Sheng Li、Wei‐Jun Tang、Wei Zhang、Rui Cao、Chao Wang、Jianliang Xiao、Dong Xue

  DOI：10.1002/anie.202108587

  日期：2021.9.20

  molecular Ni catalysis driven by light, which enables stereoretentive C-N coupling of optically active amines, amino alcohols, and amino acid esters with aryl bromides, with no need for any external photosensitizer. The method is effective for a wide variety of coupling partners, including those bearing functional groups sensitive to bases and nucleophiles, thus providing a viable alternative to accessing

  Buchwald-Hartwig CN 偶联反应已在有机合成中得到广泛应用。在过去二十年左右的时间里，已经引入了许多改进的催化剂，现在可以很容易地使用各种胺和芳基亲电试剂。然而，缺乏可用于偶联各种手性胺和芳基卤而不会侵蚀过量对映体 ( ee) 的方案）。本文报道了一种基于光驱动的分子 Ni 催化的方法，该方法能够使旋光胺、氨基醇和氨基酸酯与芳基溴进行立体保留 CN 偶联，无需任何外部光敏剂。该方法对多种偶联伙伴有效，包括那些带有对碱和亲核试剂敏感的官能团的偶联伙伴，从而为获取合成重要的手性N-芳基胺、氨基醇和氨基酸酯提供了可行的替代方案。92 个例子证明了它的可行性，ee高达 99% 。
• [EN] DIPHENYLAZETIDINONE DERIVATES POSSESSING CHOLESTEROL ABSORPTION INHIBITORY ACTIVITY<br/>[FR] DERIVES DIPHENYLAZETIDINONE A ACTIVITE INHIBITRICE DE L'ABSORPTION DU CHOLESTEROL
  申请人：ASTRAZENECA AB

  公开号：WO2005061452A1

  公开（公告）日：2005-07-07

  Compounds of formula (I) (wherein variable groups are as defined within) pharmaceutically acceptable salts, solvates, solvates of such salts and prodrugs thereof and their use as cholesterol absorption inhibitors for the treatment of hyperlipidaemia are described. Processes for their manufacture and pharmaceutical compositions containing them are also described.

  化合物的结构式（其中变量基团如定义所示）及其药学上可接受的盐、溶剂合物、该类盐的溶剂合物和它们的前药，以及它们作为治疗高脂血症的胆固醇吸收抑制剂的用途被描述。还描述了它们的制备方法和含有它们的药物组合物。