6-苄氧基吲哚-3-甲醛 | 92855-64-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 6-苄氧基吲哚-3-甲醛
• 英文名称: 6-(benzyloxy)-1H-indole-3-carbaldehyde
• 英文别名: 6-phenylmethoxy-1H-indole-3-carbaldehyde
• CAS: 92855-64-6
• 化学式: C₁₆H₁₃NO₂
• mdl: MFCD00056931
• 分子量: 251.285
• InChiKey: UUKFCVCTRWNXBI-UHFFFAOYSA-N

物化性质

• 熔点：
  215-216 °C
• 沸点：
  474.2±30.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.062
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H317,H319
• 储存条件：
  温度：2-8°C，保持惰性气体氛围。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Benzyloxyindole-3-carboxaldehyde
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: 6-Benzyloxyindole-3-carboxaldehyde
CAS number: 92855-64-6

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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: C16H13NO2
Molecular weight: 251.3

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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

反应信息

• 作为反应物：
  描述：

  6-苄氧基吲哚-3-甲醛 在 乙酸铵 、 甲醇 、 palladium on activated charcoal 、 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 6-羟基吲哚乙胺
  参考文献：
  名称：

  704. 5-羟色胺（5-羟色胺）及有关色胺的合成

  摘要：

  DOI：

  10.1039/jr9580003493
• 作为产物：
  描述：

  6-苄氧基吲哚 、 N,N-二甲基甲酰胺 在 sodium hydroxide 、 三氯氧磷 作用下， 以 水 为溶剂， 反应 1.0h， 生成 6-苄氧基吲哚-3-甲醛
  参考文献：
  名称：

  （+）-多卡霉素SA的对映选择性全合成

  摘要：

  描述了有效，简洁的对映体选择性合成有效的抗肿瘤抗生素（+）-双霉素SA的方法。本发明的路线基于一种断开策略，该策略旨在促进关键核心化合物的快速有效合成，从而能够进行临床前结构-活性关系研究。关键的三轮车核心采用高度对映选择性的吲哚氢化来建立立体中心，并随后进行了迄今未开发的替代的亲核取代/环化序列，以有效地伪造最终的吲哚环。另外，能够进行温和的化学选择性切割的稳定的磺酰胺保护基的开发大大提高了序列产量和产量。对关键反应参数的理解确保了稳定，

  DOI：

  10.1021/acs.joc.8b00285

文献信息

• An Efficient Synthetic Routeto Homocarbonyltopsentine
  作者：Benoît Joseph、Cyril Montagne、Guy Fournet

  DOI：10.1055/s-2003-40843

  日期：——

  Efficient synthesis of homocarbonyltopsentine Ia, starting from readily available triiodoimidazole 9 and 3-formylindoles 2 and 18 is described. The key steps of the synthesis are selective halogen-metal exchanges at the imidazole nucleus and subsequent addition to formylated indoles.

  介绍了一种从易得的碘代咪唑9和3-甲醛吲哚2及18出发，合成高效同羰基托品碱Ia的方法。该合成方法的关键步骤是咪唑环上选择性卤素-金属交换和随后的甲醛吲哚加成反应。
• Synthesis of Homocarbonyltopsentine Derivatives
  作者：Benoît Joseph、Cyril Montagne、Guy Fournet

  DOI：10.1055/s-2004-834905

  日期：——

  Homocarbonyltopsentines I are known to exhibit interesting anti-inflammatory activity in vivo. In order to study the role of the heterocycles in the modulation of their activity, several analogues in which indoles were replaced either by substituted indoles or by bioisosteric heterocycles such as pyrrolo[2,3-b]pyridine, benzo[b]thiophene and pyridine were synthesised. The synthesis is based on selective

  已知 Homocarbonyltopsentines I 在体内表现出有趣的抗炎活性。为了研究杂环在调节其活性中的作用，一些类似物将吲哚替换为取代的吲哚或生物等排杂环，例如吡咯并[2,3-b]吡啶、苯并[b]噻吩和吡啶被合成了。该合成基于三碘咪唑 1 上的选择性卤素-金属交换以及随后添加到甲酰化杂环上。
• Structure-Guided Design, Synthesis, and Biological Evaluation of (2-(1<i>H</i>-Indol-3-yl)-1<i>H</i>-imidazol-4-yl)(3,4,5-trimethoxyphenyl) Methanone (ABI-231) Analogues Targeting the Colchicine Binding Site in Tubulin
  作者：Qinghui Wang、Kinsie E. Arnst、Yuxi Wang、Gyanendra Kumar、Dejian Ma、Stephen W. White、Duane D. Miller、Weimin Li、Wei Li

  DOI：10.1021/acs.jmedchem.9b00706

  日期：2019.7.25

  10ab and 10bb in complex with tubulin confirmed their improved molecular interactions to the colchicine site. In vitro, biological studies showed that new ABI-231 analogues disrupt tubulin polymerization, promote microtubule fragmentation, and inhibit cancer cell migration. In vivo, analogue 10bb not only significantly inhibits primary tumor growth and decreases tumor metastasis in melanoma xenograft

  ABI-231是一种有效的，口服生物利用的微管蛋白抑制剂，可与秋水仙碱结合位点相互作用，目前正在接受前列腺癌的临床试验。在与微管蛋白复合的ABI-231晶体结构的指导下，我们围绕3-吲哚部分进行了结构-活性关系研究，从而发现了几种有效的ABI-231类似物，最著名的是10ab和10bb。与微管蛋白复合的10ab和10bb的晶体结构证实了它们与秋水仙碱位点的分子相互作用得到了改善。在体外，生物学研究表明，新的ABI-231类似物可破坏微管蛋白聚合，促进微管碎裂并抑制癌细胞迁移。体内，类似物10bb不仅在黑素瘤异种移植模型中显着抑制原发性肿瘤生长并减少肿瘤转移，而且在抗紫杉烷的PC-3 / TxR模型中显示出显着的克服紫杉醇抗性的能力。此外，药理学筛选表明10bb潜在脱靶功能的风险较低。
• Iodine-Mediated Tryptathionine Formation Facilitates the Synthesis of Amanitins
  作者：Guiyang Yao、Caroline H. Knittel、Simone Kosol、Marius T. Wenz、Bettina G. Keller、Hendrik Gruß、Alexandra C. Braun、Christian Lutz、Torsten Hechler、Andreas Pahl、Roderich D. Süssmuth

  DOI：10.1021/jacs.1c06565

  日期：2021.9.8

  provides rapid access to various new amanitin analogues. This study for the first time presents a systematic compilation of structure–activity relations (SAR) of amatoxins with regard to RNA polymerase II inhibition and cytotoxicity with one amanitin derivative of superior RNAP II inhibition. The present approach paves the way for the synthesis of structurally diverse amatoxins as future payloads for

  多肽大环化的合成方法备受关注，因为它们有助于合成各种类型的潜在生物活性化合物，例如解决蛋白质-蛋白质相互作用等目标。在此，我们报告了一种在氨基酸 Trp 和 Cys 之间的肽中构建色氨酸交联的有效方法。该反应不仅是死亡帽毒素 α-鹅膏菌素全合成的基础，而且还提供了对各种新鹅膏菌素类似物的快速获取。本研究首次系统地汇编了鹅膏菌毒素在 RNA 聚合酶 II 抑制和细胞毒性方面的构效关系 (SAR)，其中一种鹅膏菌素衍生物具有卓越的 RNAP II 抑制作用。
• [EN] INDOLE COMPOUNDS OR ANALOGUES THEREOF USEFUL FOR THE TREATMENT OF AGE-RELATED MACULAR DEGENERATION (AMD)<br/>[FR] COMPOSÉS INDOLIQUES OU ANALOGUES DE CEUX-CI UTILES DANS LE TRAITEMENT DE LA DÉGÉNÉRESCENCE MACULAIRE LIÉE À L'ÂGE (DMLA)
  申请人：NOVARTIS AG

  公开号：WO2012093101A1

  公开（公告）日：2012-07-12

  The present invention provides a compound of formula (I): a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

  本发明提供了一种公式(I)的化合物：一种制造本发明化合物的方法及其治疗用途。本发明进一步提供了一种药物活性剂的组合物和一种药物组合物。