2-(1-萘基)-2-氨基乙酸 | 97611-60-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-(1-萘基)-2-氨基乙酸
• 中文别名: 1-萘甘氨酸
• 英文名称: 2-amino-2-(naphthalen-1-yl)acetic acid
• 英文别名: D,L-(1-naphthyl)glycine；2-azaniumyl-2-naphthalen-1-ylacetate
• CAS: 97611-60-4
• 化学式: C₁₂H₁₁NO₂
• mdl: MFCD02662419
• 分子量: 201.225
• InChiKey: SCDZHZMVNQDLCM-UHFFFAOYSA-N

物化性质

• 熔点：
  240 °C
• 沸点：
  398.0±30.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2922499990
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Amino-naphthalen-1-yl-acetic acid
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: Amino-naphthalen-1-yl-acetic acid
CAS number: 97611-60-4

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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.
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: C12H11NO2
Molecular weight: 201.2

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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-(1-萘基)-2-氨基乙酸 在 palladium on activated charcoal N-甲基吗啉 、 吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 氢气 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 叔丁醇 为溶剂， -60.0~25.0 ℃ 、101.33 kPa 条件下， 反应 79.03h， 生成 Boc-D-1-Nag-Pro-Arg-H*2HOAc
  参考文献：
  名称：

  高度选择性的三肽凝血酶抑制剂。

  摘要：

  三肽醛，例如Boc-D-Phe-Pro-Arg-H（51），表现出对凝血酶的直接有效抑制作用。这种区别为设计更有效和更具选择性的丝氨酸蛋白酶抑制剂提供了重要的见识，这些抑制剂可能是有用的药理工具，并有望开发出临床有用的药物。讨论了一系列对凝血酶具有高选择性的抗凝肽的构效关系（SAR）。SAR以51的结构为基础，以一系列的二肽和三肽精氨酸醛为中心。通过用构象受限的芳香族氨基酸，芳香族氨基酸和一种氨基酸取代，研究了位置1上氨基酸残基的结构和构象作用。包含psi [CH2N]酰胺键替代物的二肽等排物。通过比较体外对胰蛋白酶，纤溶酶，Xa因子和组织纤溶酶原激活物的抑制作用，可以确定许多这些肽具有强大的抗血栓形成活性以及对凝血酶的选择性。化合物5f，D-1-Tiq-Pro-Arg-H。硫酸盐具有很高的活性，是迄今为止报道的对凝血酶最具选择性的三肽醛抑制剂。

  DOI：

  10.1021/jm00055a002
• 作为产物：
  描述：

  2-Hydroxyiminonaphth-1'-ylessigsaeure 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 2-(1-萘基)-2-氨基乙酸
  参考文献：
  名称：

  高度选择性的三肽凝血酶抑制剂。

  摘要：

  三肽醛，例如Boc-D-Phe-Pro-Arg-H（51），表现出对凝血酶的直接有效抑制作用。这种区别为设计更有效和更具选择性的丝氨酸蛋白酶抑制剂提供了重要的见识，这些抑制剂可能是有用的药理工具，并有望开发出临床有用的药物。讨论了一系列对凝血酶具有高选择性的抗凝肽的构效关系（SAR）。SAR以51的结构为基础，以一系列的二肽和三肽精氨酸醛为中心。通过用构象受限的芳香族氨基酸，芳香族氨基酸和一种氨基酸取代，研究了位置1上氨基酸残基的结构和构象作用。包含psi [CH2N]酰胺键替代物的二肽等排物。通过比较体外对胰蛋白酶，纤溶酶，Xa因子和组织纤溶酶原激活物的抑制作用，可以确定许多这些肽具有强大的抗血栓形成活性以及对凝血酶的选择性。化合物5f，D-1-Tiq-Pro-Arg-H。硫酸盐具有很高的活性，是迄今为止报道的对凝血酶最具选择性的三肽醛抑制剂。

  DOI：

  10.1021/jm00055a002

文献信息

• Sulfonic acid derivatives of hydroxamic acids and their use as medicinal products
  申请人：——

  公开号：US20030176486A1

  公开（公告）日：2003-09-18

  The present invention relates to a novel sulfonic acid derivative of hydroxamic acid or a pharmacologically acceptable salt thereof. More particularly, the present invention relates to a sulfonic acid derivative of hydroxamic acid or a pharmacologically acceptable salt thereof, which is useful as an inhibitor of lipopolysaccharides (LPS). In addition, the present invention relates to a novel intermediate compound useful for the synthesis of this sulfonic acid derivative of hydroxamic acid.

  本发明涉及羟羰酸的新型磺酸衍生物或其药理学上可接受的盐。更具体地，本发明涉及一种羟羰酸的磺酸衍生物或其药理学上可接受的盐，其用作脂多糖（LPS）的抑制剂。此外，本发明涉及一种新型中间化合物，用于合成这种羟羰酸的磺酸衍生物。
• Enzymatic Conversion of Unnatural Amino Acids by YeastD-Amino Acid Oxidase
  作者：Antonio Caligiuri、Paola D'Arrigo、Elena Rosini、Davide Tessaro、Gianluca Molla、Stefano Servi、Loredano Pollegioni

  DOI：10.1002/adsc.200606188

  日期：2006.10

  by a rational approach. With this D-amino acid oxidase variant the complete resolution of all the unnatural amino acids tested was obtained: in this case, the bioconversion requires a shorter time and a lower amount of biocatalyst compared to the wild-type enzyme. The simultaneous production of the corresponding α-keto acid, a possible precursor of the amino acid in the L-form, improves the significance

  非天然氨基酸，特别是合成的α-氨基酸，正在成为现代药物发现研究的关键工具。特别地，该申请需要对映体纯的异构体。在这项工作中，我们报告了利用酵母Rhodotorula gracilis的天然酶D-氨基酸氧化酶解析氨基酸d，1-萘基丙氨酸和d，1-萘基甘氨酸的外消旋混合物的方法。。使用通过合理方法设计的单点突变酶可以显着提高生物转化率。使用这种D-氨基酸氧化酶变体，可以完全分离出所有测试的非天然氨基酸：在这种情况下，与野生型酶相比，生物转化需要更短的时间和更少的生物催化剂。同时生产相应的α-酮酸（一种可能的L型氨基酸前体）提高了该方法的重要性。
• [EN] TOLL-LIKE RECEPTOR 4 (TLR4) INHIBITORS AND USE THEREOF<br/>[FR] INHIBITEURS DU RÉCEPTEUR 4 DE TYPE TOLL (TLR4) ET LEUR UTILISATION
  申请人：MOR RESEARCH APPLIC LTD

  公开号：WO2019224754A1

  公开（公告）日：2019-11-28

  Peptides, peptidomimetics and small molecules, collectively referred to as "decoy peptides", are provided, which interfere with binding to a TIR domain of a toll-like receptor 4 (TLR4), and inhibit a TLR4-induced signaling pathway. These decoy peptides may be useful for treating diseases associated with induction of TLR4 signaling pathway such as a disease or disorder secondary to a cardiovascular disease, sepsis or an inflammatory disease.

  提供肽、肽类似物和小分子，统称为“诱饵肽”，这些物质干扰与Toll样受体4（TLR4）的TIR结构域的结合，并抑制TLR4诱导的信号通路。这些诱饵肽可能对治疗与TLR4信号通路诱导相关的疾病有用，比如与心血管疾病、败血症或炎症性疾病相关的疾病或紊乱。
• METHOD FOR PRODUCING AMINO ACID AMINOALKYL ESTER OR INORGANIC ACID SALT THEREOF
  申请人：ASAHI KASEI KABUSHIKI KAISHA

  公开号：US20210253517A1

  公开（公告）日：2021-08-19

  The present invention provides a method for producing an amino acid aminoalkyl ester or an inorganic acid salt thereof by reacting a compound represented by general formula (I) shown below or a compound represented by general formula (III) shown below, or a salt thereof, and at least one compound selected from the group consisting of compounds represented by general formula (IV-I) shown below, compounds represented by general formula (IV-II) shown below, compounds represented by general formula (IV-III) shown below and compounds represented by general formula (IV-IV) shown below, or an inorganic acid salt thereof.

  本发明提供了一种通过使下面显示的一般式（I）所代表的化合物或下面显示的一般式（III）所代表的化合物或其盐与下面显示的一般式（IV-I）所代表的化合物、下面显示的一般式（IV-II）所代表的化合物、下面显示的一般式（IV-III）所代表的化合物和下面显示的一般式（IV-IV）所代表的化合物或其无机酸盐中的至少一种化合物反应，从而制备氨基酸氨基醇酯或其无机酸盐的方法。
• Synthesis of Quaternary α-Fluorinated α-Amino Acid Derivatives via Coordinating Cu(II) Catalytic α-C(sp³)–H Direct Fluorination
  作者：Qiang Wei、Yao Ma、Li Li、Qingfei Liu、Zijie Liu、Gang Liu

  DOI：10.1021/acs.orglett.8b03044

  日期：2018.11.16

  been developed to prepare vital quaternary α-fluorinated α-amino acid derivatives. A Cu(II) catalytic SET oxidative addition mechanism is proposed, involving a key fluoride-coupled Cu(II) charge transfer complex. The protocol can tolerate a rich variety of α-amino acids, for which the auxiliary group is removed in high yield and substituted for the direct preparation of dipeptide derivatives with detachable

  已经开发了一种配位的，铜催化的直接α-C（sp 3）-H氟化方法来制备重要的季铵化α-氟化α-氨基酸衍生物。提出了一种Cu（II）催化SET氧化加成机理，涉及一种关键的氟化物偶联的Cu（II）电荷转移配合物。该方案可以耐受多种α-氨基酸，为此，辅助基团可以高产率去除，并可以直接制备具有可分离的，单一的绝对绝对构型的目标化合物的二肽衍生物。