1-苄基-3-羟基甲基-1H-吲唑 | 131427-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 1-苄基-3-羟基甲基-1H-吲唑
• 英文名称: (1-Benzyl-1H-indazol-3-yl)-methanol
• 英文别名: (1-benzyl-1H-indazol-3-yl)methanol；1-benzyl-3-hydroxymethyl-indazole；1-benzyl-3-hydroxymethylindazole；1-benzyl-3-hydroxymethyl-1H-indazole；(1-Benzyl-1H-indazol-3-yl) methanol；(1-Benzylindazol-3-yl)methanol
• CAS: 131427-21-9
• 化学式: C₁₅H₁₄N₂O
• 分子量: 238.289
• InChiKey: AKQDXNFPEFHRLS-UHFFFAOYSA-N

物化性质

• 沸点：
  450.624℃ at 101.325kPa
• LogP：
  2.561

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (1-Benzylindazol-3-yl)methanol
Synonyms: 1-Benzyl-3-hydroxymethyl-1h-indazole

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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: (1-Benzylindazol-3-yl)methanol
CAS number: 131427-21-9

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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: C15H14N2O
Molecular weight: 238.3

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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：

  1-苄基-3-羟基甲基-1H-吲唑 在 盐酸 、 sodium hydride 、 sodium hydroxide 作用下， 以 水 、 甲苯 、 mineral oil 为溶剂， 反应 16.5h， 生成 宾达利
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION OF 1-BENZYL-3-HYDROXYMETHYL- 1H- INDAZOLE AND ITS DERIVATIVES AND REQUIRED MAGNESIUM INTERMEDIATES
  [FR] PROCÉDÉ POUR LA PRÉPARATION DE 1-BENZYL-3-HYDROXYMÉTHYL-1H-INDAZOLE ET DE SES DÉRIVÉS ET INTERMÉDIAIRES AU MAGNÉSIUM CORRESPONDANTS

  摘要：

  本发明涉及根据式（II）将1-苄基-3-羟甲基-1H-吲哚转化为根据式（I）的1-苄基-3-羟甲基-1H-吲哚的过程。

  公开号：

  WO2011015502A1
• 作为产物：
  描述：

  1-苄基-1H-吲唑-3-甲酸苄酯 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 4.0h， 以448 mg的产率得到1-苄基-3-羟基甲基-1H-吲唑
  参考文献：
  名称：

  最有效的口服活性CCK-A激动剂3-（1H-吲唑-3-基甲基）-1,5-苯并二氮杂的优化。

  摘要：

  我们先前描述了一系列3-（1H-吲唑-3-基甲基）-1,5-苯并二氮杂类CCK-A激动剂，以化合物1（GW 5823）为例，这是首次报道的结合选择性CCK-A完全激动剂，证明口服大鼠喂养模型的功效。在本报告中，我们描述了化合物1的类似物，旨在探索C3和N1药效团的变化及其对激动剂活性和受体选择性的影响。该系列中的激动剂功效受C3部分内的立体电子因素影响。CCC-A与CCK-B受体的结合亲和力几乎不依赖于C3部分的结构，但受C3上第二个取代基的性质影响。还研究了C3吲唑系列中N1-苯胺基乙酰胺“触发”部分的结构活性关系。通过改变N1-苯胺基乙酰胺部分上的取代基来调节该系列中的激动剂效力和结合亲和力。在体内小鼠胆囊排空试验中对几种类似物的评价表明，化合物1在所有测试的类似物中是最有效和最有效的。还讨论了1在大鼠中的药代动力学和药效动力学特征。

  DOI：

  10.1021/jm970265x

文献信息

• CCK or gastrin modulating benzo \x9bb!\x9b1,4! diazepines derivatives
  申请人：Glaxo Wellcome Inc.

  公开号：US05859007A1

  公开（公告）日：1999-01-12

  Benzo\x9bb!\x9b1,4!diazepine compounds of formula (I), where R.sup.1 is selected from C.sub.1 C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl, or substituted phenyl; R.sup.2 is selected from C.sub.3 -C.sub.6 alkyl, C.sub.3 C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 alkenyl, benzyl, phenylC.sub.1 -C.sub.3 alkyl of substituted phenyl; or NR.sup.1 R.sup.2 together form 1,2,3,4-tetrahydroquinoline or benzazepine, mono-, di-, or trisubstituted independently with C.sub.1-6 alkyl C.sub.1-6 alkoxy or halogen substituents; p is an integer 0 or 1; q is an integer 0 or 1; r is an integer 0 or 1; t is an integer 0 or 1, provided that when r is 0 then t is 0; R.sup.3, R.sup.5, and R.sup.6 are independently hydrogen or C.sub.1-6 alkyl; R.sup.4 is C.sub.1-6 alkyl or C.sub.1-6 alkenyl; R.sup.7 is selected from the group consisting of hydrogen, C.sub.1-6 alkyl, C.sub.1-6 cycloalkyl, C.sub.1-6 alkenyl, phenyl, substituted phenyl, napthyl, heteroaryl, substituted heteroaryl, bicycloheteroaryl or substituted bicycloheteroaryl; or NR.sup.6 R.sup.7 together form a saturated 5,6, or 7 membered ring optionally interrupted by 1,2,3 or 4 N, S or O heteroatoms, with the proviso that any two O or S atoms are not bonded to each other, m is an integer selected from the group of 0, 1, 2, 3 or 4; R.sup.8 and R.sup.9 are selected from a variety of substituents; Z is hydrogen or halogen; novel intermediates, a pharmaceutical composition for treating obesity, gall bladder stasis, disorders of pancreatic secretion, methods for such treatment and processes for preparing compounds of formula (I).

  以下是您提供的化学公式和描述的中文翻译： 本专利涉及1,4-苯并二氮杂卓化合物，其分子式为(I)，其中R1选自C1-C6烷基、C3-C6环烷基、苯基或取代苯基；R2选自C3-C6烷基、C3-C6环烷基、C3-C6烯基、苄基、苯基C1-C3烷基或取代苯基；或NR1R2共同形成1,2,3,4-四氢喹啉或苯并氮卓环，且单独或同时以C1-6烷基、C1-6烷氧基或卤素取代基进行单、双或三取代；p为0或1的整数；q为0或1的整数；r为0或1的整数；t为0或1的整数，条件是当r为0时，t也为0；R3、R5和R6独立地为氢或C1-6烷基；R4为C1-6烷基或C1-6烯基；R7选自氢、C1-6烷基、C1-6环烷基、C1-6烯基、苯基、取代苯基、萘基、杂芳基、取代杂芳基、双环杂芳基或取代双环杂芳基；或NR6R7共同形成一个由1,2,3或4个N、S或O杂原子隔断的饱和的5,6或7元环，条件是任意两个O或S原子不得相互连接；m为0、1、2、3或4的整数；R8和R9选自多种取代基；Z为氢或卤素；本专利还包括新颖的中间体、用于治疗肥胖、胆囊淤滞、胰腺分泌障碍的药物组合物，以及用于治疗这些疾病的方法和制备公式(I)化合物的方法。
• [EN] PROCESS FOR THE PREPARATION OF 1-BENZYL-3-HYDR0XYMETHYL-1H-INDAZ0LE AND ITS DERIVATIVES AND REQUIRED MAGNESIUM INTERMEDIATES<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE 1-BENZYL-3-HYDROXYMÉTHYL-1H-INDAZOLE ET DE SES DÉRIVÉS ET INTERMÉDIAIRES AU MAGNÉSIUM CORRESPONDANTS
  申请人：ACRAF

  公开号：WO2011015501A1

  公开（公告）日：2011-02-10

  The present invention relates to the process for the preparation of 1-benzyl-3-hydroxymethyl-1H-indazole according to formula (II), to be used in a subsequent process for the preparation of 1-benzyl-3- hydroxymethyl-1H-indazole according to formula (I).

  本发明涉及根据式（II）制备1-苄基-3-羟甲基-1H-吲唑的过程，用于随后根据式（I）制备1-苄基-3-羟甲基-1H-吲唑的过程。
• 一种吲唑的制备方法及其在药物合成中的应 用
  申请人：兰州大学

  公开号：CN106316958B

  公开（公告）日：2018-08-14

  本发明属于化学领域，涉及一种吲唑的制备方法及其在药物合成中的应用。本发明公开一种吲唑的制备方法及其在1H‑吲唑‑3‑羧酸、lonidamine、化合物8、化合物9、化合物10、axitinib、YD‑3、YC‑1及其类似物合成中的应用。
• Efficient two-step sequence for the synthesis of 2,5-disubstituted furan derivatives from functionalized nitroalkanes: successive Amberlyst A21- and Amberlyst 15-catalyzed processes
  作者：Alessandro Palmieri、Serena Gabrielli、Roberto Ballini

  DOI：10.1039/c0cc01097a

  日期：——

  The nitroaldol reaction of ketal-functionalized nitroalkanes with α-oxoaldehydes, promoted by Amberlyst A21, followed by acidic treatment (Amberlyst 15) of the obtained nitroalkanol, leads to the formation of 2,5-disubstituted furans in good yields. The procedure was successfully applied to the total synthesis of 1-benzyl-3-(5′-hydroxymethyl-2′-furyl)-indazole (YC-1), an important pharmaceutical target.

  在 Amberlyst A21 的促进下，酮官能化的硝基烷烃与 α-氧代醛发生硝基醛反应，然后对得到的硝基烷醇进行酸处理（Amberlyst 15），从而以良好的收率生成 2,5-二取代呋喃。该过程被成功应用于 1-苄基-3-（5′-羟甲基-2′-呋喃基）-吲唑（YC-1）的全合成，这是一种重要的药物目标物。
• [EN] PROCESSES OF MAKING 2-((1-BENZYL-1H-INDAZOL-3-YL)METHOXY)-2-METHYLPROPANOIC ACID AND ITS DERIVATIVES<br/>[FR] PROCÉDÉS DE FABRICATION D'ACIDE 2-((1-BENZYL-1H-INDAZOL-3-YL)MÉTHOXY)-2-MÉTHYLPROPANOÏQUE ET DE SES DÉRIVÉS
  申请人：TRANSLATUM MEDICUS INC

  公开号：WO2020261158A1

  公开（公告）日：2020-12-30

  The invention in this disclosure is related to the processes of making Bindarit or derivatives thereof. Specifically, the present invention provides, in part, new processes for making 2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid and its derivatives. By way of non-limiting example, synthesis and purification processes of 2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid are provided by the invention in this disclosure.

  本公开的发明涉及制备Bindarit或其衍生物的过程。具体来说，本发明部分提供了制备2-((1-苄基-1H-吲哚-3-基)甲氧基)-2-甲基丙酸及其衍生物的新工艺。举例而言，本公开的发明提供了2-((1-苄基-1H-吲哚-3-基)甲氧基)-2-甲基丙酸的合成和纯化过程。