吲哚-5-甲醇 | 1075-25-8

• 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: 吲哚-5-甲醇
• 英文名称: indole-5-methanol
• 英文别名: (1H-Indol-5-yl)-methanol；5-(hydroxymethyl)indole；(1H-indol-5-yl)methanol；1H-indol-5-ylmethanol
• CAS: 1075-25-8
• 化学式: C₉H₉NO
• mdl: MFCD02179594
• 分子量: 147.177
• InChiKey: ZSHFWQNPJMUBQU-UHFFFAOYSA-N

物化性质

• 熔点：
  66-70
• 沸点：
  360.6±17.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 危险类别：
  IRRITANT
• 安全说明：
  S24/25
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存储条件：2-8°C，密闭保存，并保持干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Indole-5-methanol
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: Indole-5-methanol
CAS number: 1075-25-8

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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: C9H9NO
Molecular weight: 147.2

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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：

  吲哚-5-甲醇 在 manganase oxide 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到5-吲哚甲醛
  参考文献：
  名称：

  二取代的新型氨基-芳基-哌啶类肾素抑制剂的发现和制备。

  摘要：

  最近，反式-二取代的氧代-芳基-哌啶已被确认为小分子非肽类肾素抑制剂，可调节高血压。在这里，我们报告发现和制备新型新型的顺式-二取代的氨基-芳基-哌啶类作为对映体的混合物，这些对映体是有效的体外肾素抑制剂，并且在双转基因小鼠模型中具有体内降压活性。

  DOI：

  10.1016/j.bmc.2004.09.056
• 作为产物：
  描述：

  5-吲哚甲醛 在 tricarbonyl(η⁴-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron 、 氢气 、 potassium carbonate 作用下， 以 异丙醇 为溶剂， 100.0 ℃ 、3.0 MPa 条件下， 反应 17.0h， 以95%的产率得到吲哚-5-甲醇
  参考文献：
  名称：

  通用，高效的铁催化醛，酮和α，β-不饱和醛的加氢反应

  摘要：

  环境友好：据报道标题为醛，酮和α，β-不饱和醛的氢化反应。在催化剂1的存在下，在温和的反应条件下以良好至优异的产率获得伯，仲和烯丙基醇。该催化剂容易且廉价地制备，并且对空气，水和柱色谱法也是稳定的。

  DOI：

  10.1002/anie.201301239

文献信息

• Practical Chemoselective Acylation: Organocatalytic Chemodivergent Esterification and Amidation of Amino Alcohols with <i>N</i> ‐Carbonylimidazoles
  作者：Hope Nelson、William Richard、Hailee Brown、Abigail Medlin、Christina Light、Stephen T. Heller

  DOI：10.1002/anie.202107438

  日期：2021.10.11

  DBU-catalyzed esterification: A single esterification product was obtained from a molecule containing primary aniline, alcohol, phenol, secondary amide, and N−H indole groups. These acylation reactions are highly practical as they involve only readily available, inexpensive, and relatively safe reagents; can be performed on a multigram scale; and can be used on carboxylic acids directly by in situ formation

  化学选择性转化是高效有机合成的基石；然而，即使是简单的转化，如酰化反应，要实现这一目标也常常是一个挑战。我们报告说，N-羰基咪唑分别在吡啶鎓离子或 1,8-二氮杂双环 [5.4.0] undec-7-ene (DBU) 存在下能够催化化学发散的苯胺或醇酰化。两种酰化反应都显示出对目标基团的高而广泛的化学选择性。在 DBU 催化的酯化中观察到了前所未有的化学选择性水平：从含有伯苯胺、醇、苯酚、仲酰胺和N的分子中获得单一酯化产物-H吲哚基团。这些酰化反应非常实用，因为它们只涉及容易获得、便宜且相对安全的试剂；可以在多克规模上进行；并且可以通过原位形成酰基咪唑亲电试剂直接用于羧酸。
• Indolinone compounds as kinase inhibitors
  申请人：Sugen, Inc.

  公开号：US06689806B1

  公开（公告）日：2004-02-10

  The invention relates to certain indolinone compounds, their method of synthesis, and a combinatorial library consisting of the indolinone compounds of the invention. The invention also relates to methods of modulating the function of protein kinases using indolinone compounds of the invention and methods of treating diseases by modulating the function of protein kinases and related signal transduction pathways.

  这项发明涉及某些吲哚酮化合物，它们的合成方法，以及由该发明的吲哚酮化合物组成的组合式文库。该发明还涉及使用该发明的吲哚酮化合物调节蛋白激酶功能的方法，以及通过调节蛋白激酶功能和相关信号转导途径治疗疾病的方法。
• [EN] VIRAL REPLICATION INHIBITORS<br/>[FR] INHIBITEURS DE REPLICATION VIRALE
  申请人：UNIV LEUVEN KATH

  公开号：WO2013045516A1

  公开（公告）日：2013-04-04

  The present invention relates to a series of novel compounds, methods to prevent or treat viral infections in animals by using the novel compounds and to said novel compounds for use as a medicine, more preferably for use as a medicine to treat or prevent viral infections, particularly infections with RNA viruses, more particularly infections with viruses belonging to the family of the Flaviviridae, and yet more particularly infections with the Dengue virus. The present invention furthermore relates to pharmaceutical compositions or combination preparations of the novel compounds, to the compositions or preparations for use as a medicine, more preferably for the prevention or treatment of viral infections. The invention also relates to processes for preparation of the compounds.

  本发明涉及一系列新化合物，通过使用这些新化合物来预防或治疗动物的病毒感染的方法，以及将这些新化合物用作药物，更好地用于治疗或预防病毒感染，特别是感染RNA病毒，更特别是感染属于黄病毒科的病毒，更特别是感染登革病毒。本发明还涉及这些新化合物的药物组合或混合制剂，用作药物的组合或制剂，更好地用于预防或治疗病毒感染。该发明还涉及这些化合物的制备方法。
• Direct and Selective 3-Amidation of Indoles Using Electrophilic <i>N</i>-[(Benzenesulfonyl)oxy]amides
  作者：Gerardo X. Ortiz、Brett N. Hemric、Qiu Wang

  DOI：10.1021/acs.orglett.7b00358

  日期：2017.3.17

  Selective C–H amidation of 1H-indoles at the C3 position is reported as a direct entry to biologically important 3-aminoindoles. This transformation is achieved using novel N-[(benzenesulfonyl)oxy]amides as electrophilic nitrogen agents in the presence of ZnCl2. Interestingly, analogous reactions in the absence of ZnCl2 resulted in the formation of indole aminal products.

  据报道，在C3位置上1 H吲哚的选择性C–H酰胺化是直接进入具有生物学重要性的3-氨基吲哚的。在ZnCl 2存在下，使用新型N -[（苯磺酰基）氧基]酰胺作为亲电氮试剂可以实现这种转化。有趣的是，在没有ZnCl 2的情况下的类似反应导致吲哚氨基产物的形成。
• Selective Oxidation of Alcohols to Esters Using Heterogeneous Co₃O₄–N@C Catalysts under Mild Conditions
  作者：Rajenahally V. Jagadeesh、Henrik Junge、Marga-Martina Pohl、Jörg Radnik、Angelika Brückner、Matthias Beller

  DOI：10.1021/ja403615c

  日期：2013.7.24

  Novel cobalt-based heterogeneous catalysts have been developed for the direct oxidative esterification of alcohols using molecular oxygen as benign oxidant. Pyrolysis of nitrogen-ligated cobalt(II) acetate supported on commercial carbon transforms typical homogeneous complexes to highly active and selective heterogeneous Co3O4-N@C materials. By applying these catalysts in the presence of oxygen, the

  新型钴基多相催化剂已被开发用于使用分子氧作为良性氧化剂对醇进行直接氧化酯化。商业碳上载氮连接的乙酸钴 (II) 的热解将典型的均质配合物转化为高活性和选择性的异质 Co3O4-N@C 材料。通过在氧气存在下使用这些催化剂，醇的交叉和自酯化以良好的产率进行。