(R)-3-叔丁氧羰基氨基-4-苯基丁酸 | 101555-61-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 其他氨基酸衍生物
• 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)-3-叔丁氧羰基氨基-4-苯基丁酸
• 中文别名: Boc-D-β-高苯丙氨酸；BOC-(R)-3-氨基-4-苯丁酸；BOC-D-BETA-高苯丙氨酸
• 英文名称: (R)-3-t-butoxycarbonylamino-4-phenylbutyric acid
• 英文别名: (3R)-3-{[(tert-butoxy)carbonyl]amino}-4-phenylbutanoic acid；(3R)-3-[(tert-butoxycarbonyl)amino]-4-phenylbutanoic acid；(R)-3-((tert-butoxycarbonyl)amino)-4-phenylbutanoic acid；(R)-3-(tert-butyloxycarbonylamino)-4-phenylbutanoic acid；(R)-β-[[(1,1-dimethylethoxy)carbonyl]amino]benzenebutanoic acid；Boc-β-homo-D-Phe；Boc-d-beta-homophenylalanine；(3R)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutanoic acid
• CAS: 101555-61-7
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: ACKWQHCPHJQANL-GFCCVEGCSA-N

物化性质

• 熔点：
  100-102oC
• 沸点：
  444.8±38.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S24/25
• 危险类别码：
  R22
• 海关编码：
  2924299090
• 危险标志：
  GHS07
• 危险性描述：
  H302
• 危险性防范说明：
  P280,P305+P351+P338
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-D-beta-homophenylalanine
Synonyms: (R)-3-(Boc-amino)-4-phenylbutyric acid

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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: Boc-D-beta-homophenylalanine
CAS number: 101555-61-7

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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: C15H21NO4
Molecular weight: 279.3

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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

(R)-3-叔丁氧羰基氨基-4-苯基丁酸可用于制备具有特定结构的PDE4和PDE5抑制剂。

该化合物是一种氨基酸衍生物，可以通过以下四个步骤从D-苯丙氨酸合成得到：(R)-3-叔丁氧羰基氨基-4-苯基丁酸。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(R)-tert-butyl 4-hydroxy-1-phenylbutan-2-ylcarbamate	177839-89-3	C15H23NO3	265.353
  ——	(R)-tert-butyl (1-cyano-3-phenylpropan-2-yl)carbamate	145149-49-1	C15H20N2O2	260.336
  N-Boc-D-苯丙氨醇	N-tert-butoxycarbonyl-D-Phenylalaninol	106454-69-7	C14H21NO3	251.326
  Boc-D-苯丙氨酸	Boc-D-Phe-OH	18942-49-9	C14H19NO4	265.309
  2-氨基-4-苯基丁酸	(R)-3-amino-4-phenylbutanoic acid	131270-08-1	C10H13NO2	179.219
  ——	(R)-2-((tert-butoxycarbonyl)amino)-3-phenylpropyl methanesulfonate	126301-19-7	C15H23NO5S	329.417

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	methyl 3-(R)-[N-(tert-butoxycarbonyl)amino]-4-phenylbutanoate	115313-20-7	C16H23NO4	293.363
  ——	(R)-tert-butyl 4-hydroxy-1-phenylbutan-2-ylcarbamate	177839-89-3	C15H23NO3	265.353
  ——	N-[(2R)-1-carbamoyl-3-phenylpropan-2-yl]carbamic acid tert-butyl ester	200949-32-2	C15H22N2O3	278.351
  ——	((R)-1-Benzyl-2-hydroxycarbamoylethyl)carbamic Acid t-Butyl Ester	1092951-01-3	C15H22N2O4	294.351
  ——	(R)-tert-butyl (1-cyano-3-phenylpropan-2-yl)carbamate	145149-49-1	C15H20N2O2	260.336
  ——	(2S)-2-[3'-(tert-Butoxycarbonyl)amino-3'-(R)-benzylpropanoyloxy]-4-methylpentanoic Acid	——	C21H31NO6	393.48
  ——	allyl (2S)-2-[3'-N-(tert-Butoxycarbonyl)amino-3'-(R)-benzylpropanoyloxy]-4-methylpentanoate	193070-97-2	C24H35NO6	433.545

反应信息

• 作为反应物：
  描述：

  (R)-3-叔丁氧羰基氨基-4-苯基丁酸 在 三聚氯氰 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 (R)-tert-butyl (1-cyano-3-phenylpropan-2-yl)carbamate
  参考文献：
  名称：

  [EN] SEVEN-MEMBERED SULFONAMIDES AS MODULATORS OF RAR-RELATED ORPHAN RECEPTOR-GAMMA (RORgamma, NR1F3)
  [FR] SULFONAMIDES À SEPT CHAÎNONS COMME MODULATEURS DES RÉCEPTEURS GAMMA ORPHELINS ASSOCIÉS À UN RÉCEPTEUR DE L'ACIDE RÉTINOÏQUE (RORGamma, NR1F3)

  摘要：

  这项发明提供了孤儿核受体RORγ的调节剂，以及通过向需要治疗RORγ介导疾病的人类或哺乳动物施用这些新型RORγ调节剂的方法。具体而言，本发明提供了式（1）的化合物及其对映体、二对映体、互变异构体、溶剂化合物和药学上可接受的盐，以及包含所述化合物作为活性成分的药物组合物。

  公开号：

  WO2013064231A1
• 作为产物：
  描述：

  N-Boc-D-苯丙氨醇 在 氢氧化钾 作用下， 以 吡啶 、 甲醇 、 二甲基亚砜 为溶剂， 反应 37.0h， 生成 (R)-3-叔丁氧羰基氨基-4-苯基丁酸
  参考文献：
  名称：

  Syntheses and biological activities of bombesin analogs modified in the C-terminal dipeptide part

  摘要：

  Bombesin receptor antagonists are possible therapeutic agents due to their ability to act as inhibitors of cellular proliferation. On the basis of our hypothesis on the mechanism of action of gastrin associating an activating enzyme system to the receptor and on the results reported in the litterature, we have synthesized bombesin analogues which have been modified in the C-terminal Leu(13)-Leu(14) amide part. We have shown that modification in the C-terminal part of the bombesin strongly affected the biological activity in rat pancreatic acini. The most potent compound which is described here, H-D-Phe- Gln-Trp-Ala-Val-Gly-His-Leu-psi(CH2)Leu-NH2, was able to recognize the bombesin receptor on rat pancreatic acini (Ki 4.3 nM) and antagonized the bombesin stimulated amylase secretion (Ki 7.7 nM).

  DOI：

  10.1016/s0223-5234(99)80063-4

文献信息

• Amino-substituted heterocycles, compositions thereof, and methods of treatment therewith
  申请人：D'Sidocky Neil R.

  公开号：US20080242694A1

  公开（公告）日：2008-10-02

  Provided herein are Heterocyclic Compounds having the following structure: wherein R 1 , R 2 , X, Y and Z are as defined herein, compositions comprising an effective amount of a Heterocyclic Compound and methods for treating or preventing cancer, inflammatory conditions, immunological conditions, metabolic conditions and conditions treatable or preventable by inhibition of a kinase pathway comprising administering an effective amount of a Heterocyclic Compound to a patient in need thereof.

  本文提供具有以下结构的杂环化合物： 其中R1、R2、X、Y和Z如本文所定义，包含有效量杂环化合物的组合物，以及治疗或预防癌症、炎症性疾病、免疫疾病、代谢性疾病以及通过给予患者需要的有效量杂环化合物来抑制激酶途径治疗或预防的疾病的方法。
• NOVEL COMPOUNDS FOR MEDICAL USE AS PEPTIDASE EFFECTORS
  申请人：ANSORGE Siegfried

  公开号：US20120028995A1

  公开（公告）日：2012-02-02

  The invention relates to compounds of general formula (I) as set forth in the claims as well as to the use of the compounds of the general formula (1) in the medical field, specifically for use in the suppression of DNA synthesis and inflammatory cytokine production as well as in the stimulation of anti-inflammatory cytokine production in vitro and in vivo. This abstract is neither intended to define the invention disclosed in this specification nor intended to limit the scope of the invention in any way.

  该发明涉及一般式（I）所述的化合物，以及该一般式（1）化合物在医学领域中的使用，具体用于抑制DNA合成和炎症细胞因子的产生，以及在体外和体内刺激抗炎细胞因子的产生。本摘要既不旨在定义本说明书中披露的发明，也不旨在以任何方式限制发明的范围。
• [EN] DITERPENOID COMPOUNDS THAT ACT ON PROTEIN KINASE C (PKC)<br/>[FR] COMPOSÉS DITERPÉNOÏDES AGISSANT SUR LA PROTÉINE KINASE C (PKC)
  申请人：K GEN INC

  公开号：WO2021062030A1

  公开（公告）日：2021-04-01

  This present disclosure relates to protein kinase C (PKC) modulating compounds, methods of treating a subject with cancer using the compounds, and combination treatments with a second therapeutic agent.

  本公开涉及蛋白激酶C（PKC）调节化合物，使用这些化合物治疗癌症患者的方法，以及与第二治疗剂联合治疗的方法。
• [EN] NOVEL PHTHALAZINONE-PYRROLOPYRIMIDINECARBOXAMIDE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS DE PHTALAZINONE-PYRROLOPYRIMIDINECARBOXAMIDE
  申请人：NYCOMED GMBH

  公开号：WO2012171900A1

  公开（公告）日：2012-12-20

  The compounds of formula (1), in which R1, R7, R8, R9, R10, R17, R18, R19, R20 and m have the meanings as given in the description, are novel effective inhibitors of type 4 and 5 phosphodiesterase.

  式（1）中的化合物，其中R1、R7、R8、R9、R10、R17、R18、R19、R20和m的含义如描述中所述，是新颖的有效的4型和5型磷酸二酯酶抑制剂。
• NOVEL PHTHALAZINONE-PYRROLOPYRIMIDINECARBOXAMIDE DERIVATIVES
  申请人：Stengel Thomas

  公开号：US20140112945A1

  公开（公告）日：2014-04-24

  The compounds of formula (1) in which R1, R7, R8, R9, R10, R17, R18, R19, R20 and m have the meanings as given in the description, are novel effective inhibitors of type 4 and type 5 phosphodiesterase.

  式（1）中的化合物，其中R1、R7、R8、R9、R10、R17、R18、R19、R20和m的含义如描述中所述，是新颖的有效的磷酸二酯酶4型和5型抑制剂。