4-((苄氧基羰基氨基)甲基)苯硼酸 | 914452-61-2

• 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: 4-((苄氧基羰基氨基)甲基)苯硼酸
• 中文别名: 4-((苄氧羰基氨基)甲基)苯基硼酸
• 英文名称: 4-(Cbz-aminomethyl)phenyboronic acid
• 英文别名: (4-((((benzyloxy)carbonyl)amino)methyl)phenyl)boronic acid；α-benzyloxycarbonylamino-p-toluoylboronic acid；[4-(phenylmethoxycarbonylaminomethyl)phenyl]boronic acid
• CAS: 914452-61-2
• 化学式: C₁₅H₁₆BNO₄
• 分子量: 285.107
• InChiKey: IFXKQHGDWGCLKL-UHFFFAOYSA-N

物化性质

• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.79
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2931900090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-((Benzyloxycarbonylamino)methyl)phenylboronic acid
Synonyms: 4-(Cbz-aminomethyl)phenyboronic 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: 4-((Benzyloxycarbonylamino)methyl)phenylboronic acid
CAS number: 914452-61-2

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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: C15H16BNO4
Molecular weight: 285.1

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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：

  4-((苄氧基羰基氨基)甲基)苯硼酸 在 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium 10% on activated carbon 、 氢气 、 palladium diacetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 1.0h， 生成 4'-氨甲基-2-氰基联苯
  参考文献：
  名称：

  Sequential One-Pot Access to Molecular Diversity through Aniline Aqueous Borylation

  摘要：

  On the basis of our recently reported aniline aqueous borylation, molecular diversity was achieved in a one-pot process by combining other reactions such as esterification, Suzuki-Miyaura coupling, hydrogenolysis, or Petasis borono-Mannich.

  DOI：

  10.1021/jo501665e
• 作为产物：
  描述：

  4-氨基苄胺 在 盐酸 、 三乙胺 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.83h， 生成 4-((苄氧基羰基氨基)甲基)苯硼酸
  参考文献：
  名称：

  Sequential One-Pot Access to Molecular Diversity through Aniline Aqueous Borylation

  摘要：

  On the basis of our recently reported aniline aqueous borylation, molecular diversity was achieved in a one-pot process by combining other reactions such as esterification, Suzuki-Miyaura coupling, hydrogenolysis, or Petasis borono-Mannich.

  DOI：

  10.1021/jo501665e

文献信息

• [EN] ANTIBODIES AGAINST SEROTONIN, TRYPTOPHAN AND KYNURENINE METABOLITES AND USES THEREOF<br/>[FR] ANTICORPS DIRIGÉS CONTRE DES MÉTABOLITES DE SÉROTONINE, DE TRYPTOPHANE ET DE KYNURÉNINE ET LEURS UTILISATIONS
  申请人：NESTEC SA

  公开号：WO2016079708A1

  公开（公告）日：2016-05-26

  The present invention provides antibodies and methods for preparing antibodies to metabolites in the serotonin, tryptophan and kynurenine pathways, such as 5- hydroxyindole-3-acetic acid (5-HIAA), melatonin (MT) and kynurenic acid (KYNA). The specific metabolite antibodies have low cross-reactivity to structurally related metabolites, and are useful reagents for specific and sensitive immunoassays. The present invention also provides methods for using such antibodies to measure the levels of 5-HIAA, melatonin, or kynurenic acid in biological samples from human patients.

  本发明提供了抗体和制备抗体的方法，用于代谢物在血清素、色氨酸和酮喹酮途径中，如5-羟基吲哚-3-乙酸（5-HIAA）、褪黑激素（MT）和喹酮酸（KYNA）。特定的代谢物抗体对结构相关的代谢物具有低的交叉反应性，并且是用于特定和敏感免疫测定的有用试剂。本发明还提供了使用这些抗体来测量人类患者生物样本中5-HIAA、褪黑激素或喹酮酸水平的方法。
• Development of Alkylated Hydrazides as Highly Potent and Selective Class I Histone Deacetylase Inhibitors with T cell Modulatory Properties
  作者：Ping Sun、Jing Wang、Khadija S. Khan、Weiqin Yang、Billy Wai-Lung Ng、Nikita Ilment、Matthes Zessin、Emre F. Bülbül、Dina Robaa、Frank Erdmann、Matthias Schmidt、Christophe Romier、Mike Schutkowski、Alfred Sze-Lok Cheng、Wolfgang Sippl

  DOI：10.1021/acs.jmedchem.2c01132

  日期：2022.12.22

  Histone deacetylases (HDACs) are epigenetic regulators and additionally control the activity of non-histone substrates. We recently demonstrated that inhibition of HDAC8 overexpressed in various of cancers reduces hepatocellular carcinoma tumorigenicity in a T cell-dependent manner. Here, we present alkylated hydrazide-based class I HDAC inhibitors in which the n-hexyl side chain attached to the hydrazide

  组蛋白脱乙酰酶 (HDAC) 是表观遗传调节剂，另外还控制非组蛋白底物的活性。我们最近证明，抑制在各种癌症中过表达的 HDAC8 会以 T 细胞依赖性方式降低肝细胞癌的致瘤性。在这里，我们提出了基于烷基化酰肼的 I 类 HDAC 抑制剂，其中连接到酰肼部分的正己基侧链在体外表现出 HDAC8 选择性。对最有希望的化合物7d对 HDAC8的抑制模式的分析揭示了一种底物竞争性结合模式。7d显着诱导 HDAC8 底物 H3K27 和 SMC3 的乙酰化，但不诱导 CD4 +中的微管蛋白T 淋巴细胞，并显着上调记忆和效应功能的基因表达。此外，在 C57BL/6 小鼠中腹腔注射7d（10 mg/kg）可增加CD4 + T 细胞和 CD8 + T 细胞比例中的白细胞介素 2表达，且无明显毒性。本研究扩展了具有 T 细胞调节特性的 HDAC8 抑制剂的新型化学型，用于未来的治疗应用。
• Hydroxylamine Umpolung in Copper-Catalyzed Cross-Coupling Reactions to Synthesize <i>N</i>-Arylhydroxylamine Derivatives
  作者：Gary Mathieu、Emna Azek、Calvine Lai、Hélène Lebel

  DOI：10.1021/acscatal.3c06020

  日期：2024.4.5

  chemistry to synthesize a reagent for the transfer of an electrophilic N–O moiety. Reagent 2 is a hydroxylamine umpolung that allows the formation of highly valuable N-arylhydroxylamine synthons via a copper-catalyzed cross-coupling reaction with boronic acids. The process with reagent 2 showed a wide functional group tolerance, especially with other electrophilic functional groups, and exhibited an orthogonal

  羟胺衍生物是成熟的氮前体，可通过氮-氧键的断裂经历各种过渡金属催化的转化。相反，由于 N-O 键固有的脆弱性，含有可转移亲电子羟胺的试剂的开发一直难以实现。在此，我们展示了高价碘化学在合成用于亲电子 N-O 部分转移的试剂中的效用。试剂2是一种羟胺极化，可通过铜催化的与硼酸的交叉偶联反应形成高价值的N-芳基羟胺合成子。使用试剂2的方法显示出广泛的官能团耐受性，特别是对其他亲电官能团的耐受性，并且与合成N-芳基羟胺衍生物的其他方法相比表现出正交反应性。这些可以进行 Cope 重排和后官能化，提供各种含氮结构单元。实验和计算机机理研究提出了一种催化循环，其中第一步涉及形成铜（II）-羟胺物质。然后该物质与硼酸反应产生所需的产物。
• WO2006/117548
  申请人：——

  公开号：——

  公开（公告）日：——
• Chemoselective Primary Amination of Aryl Boronic Acids by P^III/P^V═O-Catalysis: Synthetic Capture of the Transient Nef Intermediate HNO
  作者：Seung Youn Hong、Alexander T. Radosevich

  DOI：10.1021/jacs.2c02922

  日期：2022.5.25