1-甲苯基-3-吲哚硼酸 | 149108-61-2

• 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: 1-甲苯基-3-吲哚硼酸
• 英文名称: 1-tosyl-1H-indol-3-boronic acid
• 英文别名: N-tosyl-3-indolylboronic acid；[1-(4-methylbenzenesulfonyl)-1H-indol-3-yl]boronic acid；(1-tosyl-1H-indol-3-yl)boronic acid；N-(p-Toluenesulfonyl)indole-3-boronic acid；[1-(4-methylphenyl)sulfonylindol-3-yl]boronic acid
• CAS: 149108-61-2
• 化学式: C₁₅H₁₄BNO₄S
• 分子量: 315.157
• InChiKey: XADMCCFJOAXDPE-UHFFFAOYSA-N

物化性质

• 沸点：
  581.5±60.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.87
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  87.9
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  -20°C，干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N-(P-Toluenesulfonyl)indole-3-boronic 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: N-(P-Toluenesulfonyl)indole-3-boronic acid
CAS number: 149108-61-2

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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, under −20◦C.
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: C15H14BNO4S
Molecular weight: 315.2

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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, sulfur 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：

  1-甲苯基-3-吲哚硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 盐酸 、 potassium phosphate 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.0h， 生成 6α-(N-tosylindol-3-yl)androst-4-ene-3,17-dione
  参考文献：
  名称：

  Suzuki-Miyaura 交叉偶联反应中的 6-氯代和 6-溴代类固醇。通往潜在芳香酶抑制剂的便捷途径

  摘要：

  类固醇中 sp 2 -碳上的氯已被证明在与 Ni 或 Pd 催化剂的 Suzuki-Miyaura 交叉偶联反应中具有反应性。类似的 6-溴衍生物的偶联也已被证明适用于更广泛的底物。6-溴-Δ 3 , 5-甾体烯醇醚的 Suzuki-Miyaura 芳基化以及随后的水解是获得在饱和碳上带有芳基的 6-芳基化甾体的有用途径。

  DOI：

  10.1055/s-2006-926270
• 作为产物：
  描述：

  3-iodo-1-tosyl-1-indole 在 甲醇 、 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 1.5h， 生成 1-甲苯基-3-吲哚硼酸
  参考文献：
  名称：

  3-（1H-吲哚-3-基）-5-（1H-吲哚-3-羰基）-4-羟基糠酸的区域选择性合成：通往基于羟基糠酸的胰岛素受体激活剂的途径

  摘要：

  报道了一种新型的用羟基糠酸代替羟基醌部分的胰岛素受体活化剂。3-（1所述的合成ħ -吲哚-3-基）-5-（1- ħ -吲哚-3-羰基）-4- hydroxyfuroic酸（26 - 30）需要七个主要步骤。合成的关键要素包括：（1）依次制备两种4-（N-保护的吲哚）-3-甲氧基-糠醛2,5-二羧酸酯（4和6）；（2）用氯甲酸甲酯将糠酸二酸8区域选择性转化为其C-5甲基酯10; （3）酰化10在温和条件下用7位取代的吲哚 这项研究证明了用羟基糠酸支架合成胰岛素受体激活剂的可行途径。在那些羟基糠酸化合物中，化合物28具有与具有二羟基苯醌支架的默克化合物2相当的胰岛素受体激活潜能。Drug Dev Res 72：247–258，2011.©2010 Wiley-Liss，Inc.

  DOI：

  10.1002/ddr.20391

文献信息

• [EN] MTH1 INHIBITORS FOR TREATMENT OF INFLAMMATORY AND AUTOIMMUNE CONDITIONS<br/>[FR] INHIBITEURS DE MTH1 DESTINÉS AU TRAITEMENT DES ÉTATS INFLAMMATOIRES ET AUTO-IMMUNS
  申请人：THOMAS HELLEDAYS STIFTELSE FÖR MEDICINSK FORSKNING

  公开号：WO2015187089A1

  公开（公告）日：2015-12-10

  A compound of formula (I), or a pharmaceutically acceptable salt thereof, for use in the treatment of autoimmune diseases and inflammatory conditions.

  化合物的化学式（I），或其药学上可接受的盐，用于治疗自身免疫性疾病和炎症性疾病。
• [EN] PYRIMIDINE-2,4-DIAMINE DERIVATIVES FOR TREATMENT OF CANCER<br/>[FR] DÉRIVÉS DE PYRIMIDINE-2,4-DIAMINE UTILISABLES EN VUE DU TRAITEMENT DU CANCER
  申请人：THOMAS HELLEDAYS STIFTELSE FÖR MEDICINSK FORSKNING

  公开号：WO2014084778A1

  公开（公告）日：2014-06-05

  A compound of formula (I), or a pharmaceutically-acceptable salt thereof. The compound is useful in the treatment of cancer or other diseases that may benefit from inhibition of MTH1.

  公式(I)的化合物，或其药用可接受的盐。该化合物可用于治疗癌症或其他可能从抑制MTH1中受益的疾病。
• Palladium-Catalyzed Preparation of Weinreb Amides from Boronic Acids and <i>N</i>-Methyl-<i>N</i>-methoxycarbamoyl Chloride
  作者：Ravi Krishnamoorthy、Sang Q. Lam、Christopher M. Manley、R. Jason Herr

  DOI：10.1021/jo902647h

  日期：2010.2.19

  A simple protocol for the synthesis of Weinreb benzamides and α,β-unsaturated Weinreb amides through a palladium-catalyzed cross-coupling reaction between organoboronic acids and N-methoxy-N-methylcarbamoyl chloride has been developed. The method is also applicable to the use of potassium organotrifluoroborates.

  已经开发了通过有机硼酸与N-甲氧基-N-甲基氨基甲酰氯之间的钯催化交叉偶联反应合成Weinreb苯甲酰胺和α，β-不饱和Weinreb酰胺的简单方案。该方法也适用于有机三氟硼酸钾的使用。
• 一种铁催化羰基化合成二芳甲酮的方法
  申请人：南京师范大学

  公开号：CN106116999B

  公开（公告）日：2019-02-01

  本发明公开了一种铁催化羰基化合成二芳甲酮类化合物的方法，属于催化合成技术领域。本发明在溶剂醇或醇的水溶液中，在碱、酸和碘化物的作用下，加入铁催化剂，催化芳基卤代物、芳硼类化合物与卤仿或四卤化碳羰基源直接交叉偶联反应制备二芳甲酮类化合物。本发明的偶联反应制备二芳甲酮类化合物的方法，具有羰基源安全、廉价和易于处理；催化剂来源广泛、廉价和毒性小；反应无需配体且活性好；反应条件温和且选择性高；底物来源广泛且稳定；底物官能团相容性好且底物的适用范围广；反应介质绿色且可以循环回收。在优化的反应条件之下，目标产品分离收率高达94％。
• The First Total Synthesis of Dragmacidin D
  作者：Neil K. Garg、Richmond Sarpong、Brian M. Stoltz

  DOI：10.1021/ja027822b

  日期：2002.11.1

  The first total synthesis of the biologically significant bis-indole alkaloid dragmacidin D (5) has been achieved. Thermal and electronic modulation provides the key for a series of palladium-catalyzed Suzuki cross-coupling reactions that furnished the core structure of the complex guanidine- and aminoimidazole-containing dragmacidins. Following this crucial sequence, a succession of meticulously controlled

  已经实现了具有生物学意义的双吲哚生物碱 Dragmacidin D (5) 的首次全合成。热和电子调制为一系列钯催化的 Suzuki 交叉偶联反应提供了关键，这些反应提供了含有胍和氨基咪唑的复杂药物的核心结构。按照这个关键的顺序，一系列精心控制的最终事件被开发出来，导致天然产品的完成。