(4-甲氧基羰基甲基)苯硼酸 | 454185-96-7

• 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-甲氧基羰基甲基)苯硼酸
• 中文别名: (4-甲氧羰基甲基)苯基硼酸；4-(2-甲氧基-2-氧代乙基)苯硼酸
• 英文名称: [4-(2-methoxy-2-oxoethyl)phenyl]boronic acid
• 英文别名: 4-(methoxycarbonylmethyl)phenylboronic acid；(4-(2-Methoxy-2-oxoethyl)phenyl)boronic acid
• CAS: 454185-96-7
• 化学式: C₉H₁₁BO₄
• mdl: MFCD09997796
• 分子量: 193.995
• InChiKey: CKXOGMXYISAZGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 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: (4-Methoxycarbonylmethyl)phenylboronic acid
Synonyms: Methyl (4-boronophenyl)acetate

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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-Methoxycarbonylmethyl)phenylboronic acid
CAS number: 454185-96-7

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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, refrigerated.
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: C9H11BO4
Molecular weight: 194.0

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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.

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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-甲氧基羰基甲基)苯硼酸 在 palladium on activated charcoal 吡啶 、 盐酸 、 lithium hydroxide 、 sodium chlorite 、 disodium hydrogenphosphate 、 4 A molecular sieve 、 四丁基氟化铵 、 氢气 、 copper diacetate 、 戴斯-马丁氧化剂 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 间苯二酚 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 145.0h， 生成
  参考文献：
  名称：

  （-）-tejedine的第一个对映选择性全合成。

  摘要：

  [结构：见正文]报告了（-）-tejedine（1）的第一个对映选择性全合成。Tejedine是一种1998年从小Ber小isolated中提取的次要成分的癸二双苄基四氢异喹啉。合成是通过采用四个关键步骤的策略实现的，包括手性辅助非对映选择性Bischler-Napieralski环化。

  DOI：

  10.1021/ol0261635
• 作为产物：
  描述：

  4-羟基苯乙酸甲酯 在 2,6-二甲基吡啶 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 二乙醇胺 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 异丙醇 为溶剂， 生成 (4-甲氧基羰基甲基)苯硼酸
  参考文献：
  名称：

  （-）-tejedine的第一个对映选择性全合成。

  摘要：

  [结构：见正文]报告了（-）-tejedine（1）的第一个对映选择性全合成。Tejedine是一种1998年从小Ber小isolated中提取的次要成分的癸二双苄基四氢异喹啉。合成是通过采用四个关键步骤的策略实现的，包括手性辅助非对映选择性Bischler-Napieralski环化。

  DOI：

  10.1021/ol0261635

文献信息

• A general approach to C-Acyl glycosides via palladium/copper Co-catalyzed coupling reaction of glycosyl carbothioates and arylboronic acids
  作者：Li-Na Wang、You-Hong Niu、Qing-Hui Cai、Qin Li、Xin-Shan Ye

  DOI：10.1016/j.tet.2021.131955

  日期：2021.2

  A general and efficient approach to the synthesis of various C-acyl glycosides has been developed via Pd2(dba)3/CuTC co-catalyzed cross-coupling reaction of glycosyl carbothioates with arylboronic acids. The reaction showed a broad substrate scope and 25 examples were exhibited in 61%–97% isolated yields. Furthermore, this reaction was applied to the gram-scale preparation of C-acyl glycosides. The

  通过Pd 2（dba）3 / CuTC共催化的糖基硫代糖基酸酯与芳基硼酸的交叉偶联反应，已经开发了一种合成各种C-酰基糖苷的通用有效方法。该反应显示出较宽的底物范围，其中25个实例的分离产率为61％–97％。此外，该反应被用于克规模的C-酰基糖苷的制备。偶联的产物可以进一步转化为多种生物学上有用的化合物，例如通过合成保护的Sergliflozin-A模拟物。
• Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes and Quaternary Arylammonium Salts
  作者：Adelphe M. Mfuh、John D. Doyle、Bhuwan Chhetri、Hadi D. Arman、Oleg V. Larionov

  DOI：10.1021/jacs.6b01376

  日期：2016.3.9

  We report herein a simple, metal- and additive-free, photoinduced borylation of haloarenes, including electron-rich fluoroarenes, as well as arylammonium salts directly to boronic acids. This borylation method has a broad scope and functional group tolerance. We show that it can be further extended to boronic esters and carried out on gram scale as well as under flow conditions.

  我们在此报告了一种简单的、无金属和无添加剂的、光诱导的卤代芳烃硼化反应，包括富电子氟芳烃，以及芳基铵盐直接转化为硼酸。这种硼酸化方法具有广泛的范围和官能团耐受性。我们表明它可以进一步扩展到硼酸酯并在克级以及在流动条件下进行。
• Substituted Benzo-Imidazo-Pyrido-Diazepine Compounds
  申请人：Ashwell Mark A.

  公开号：US20120108574A1

  公开（公告）日：2012-05-03

  The present invention relates to substituted benzo-imidazo-pyrido-diazepine compounds and methods of synthesizing these compounds. The present invention also relates to pharmaceutical compositions containing substituted benzo-imidazo-pyrido-diazepine compounds and methods of treating cell proliferative disorders, such as cancer, by administering these compounds and pharmaceutical compositions to subjects in need thereof.

  本发明涉及取代的苯并咪唑吡啶二氮杂化合物及其合成方法。本发明还涉及含有取代的苯并咪唑吡啶二氮杂化合物的药物组合物，以及通过向需要的主体施用这些化合物和药物组合物来治疗细胞增殖性障碍，如癌症的方法。
• Discovery of a Novel Series of Biphenyl Benzoic Acid Derivatives as Potent and Selective Human β₃-Adrenergic Receptor Agonists with Good Oral Bioavailability. Part I
  作者：Masashi Imanishi、Yasuyo Tomishima、Shinji Itou、Hitoshi Hamashima、Yutaka Nakajima、Kenichi Washizuka、Minoru Sakurai、Shigeo Matsui、Emiko Imamura、Koji Ueshima、Takao Yamamoto、Nobuhiro Yamamoto、Hirofumi Ishikawa、Keiko Nakano、Naoko Unami、Kaori Hamada、Yasuhiro Matsumura、Fujiko Takamura、Kouji Hattori

  DOI：10.1021/jm701324c

  日期：2008.3.1

  A novel class of biphenyl analogues containing a benzoic acid moiety based on lead compound 8i have been identified as potent and selective human beta 3 adrenergic receptor (beta 3-AR) agonists with good oral bioavailability and long plasma half-life. After further substituent effects were investigated at the terminal phenyl ring of lead compound 8i, we have discovered that more lipophilic substitution

  一种新型的含有基于铅化合物8i的苯甲酸部分的联苯类似物已被鉴定为具有良好口服生物利用度和长血浆半衰期的有效和选择性的人β3肾上腺素能受体（β3-AR）激动剂。在研究了铅化合物8i的末端苯环上的进一步取代基作用后，我们发现R位置的更多亲脂取代提高了效能和选择性。这些研究的结果是，在效力，选择性和药代动力学方面取得了最佳平衡，确定了10a和10e是领先的候选药物。另外，评价化合物10a和10e对于由卡巴胆碱引起的膀胱内压力升高是有效的，例如在麻醉狗中膀胱过度活动模型。
• Efficient cyclopropanation of aryl/heteroaryl acetates and acetonitriles with vinyl diphenyl sulfonium triflate
  作者：Mingwei Zhou、Yimin Hu、Ke En、Xuefei Tan、Hong C. Shen、Xuhong Qian

  DOI：10.1016/j.tetlet.2018.02.080

  日期：2018.4

  A convenient method was developed for the cyclopropanation of aryl acetates and aryl acetonitrile using vinyl diphenyl sulfonium triflate salt. The newly developed conditions are simple, mild, and compatible with a wide range of functional groups, without the need to apply an inert atmosphere, or alkali bases.

  开发了一种方便的方法，该方法使用乙烯基二苯基sulf三氟甲磺酸盐对乙酸芳基酯和芳基乙腈进行环丙烷化。新开发的条件简单，温和，并且与各种官能团兼容，而无需施加惰性气氛或碱金属。