1-BOC-6-甲基吲哚 | 127956-24-5

• 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: 1-BOC-6-甲基吲哚
• 英文名称: tert-butyl 6-methyl-1H-indole-1-carboxylate
• 英文别名: tert-butyl 6-methylindole-1-carboxylate
• CAS: 127956-24-5
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: MUQBSROSSKTUQW-UHFFFAOYSA-N

物化性质

• 沸点：
  337.3±35.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-BOC-6-methylindole, tech grade
Synonyms: t-Butyl 6-methyl-1H-indole-1-carboxylate

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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-BOC-6-methylindole, tech grade
CAS number: 127956-24-5

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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.
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: C14H17NO2
Molecular weight: 231.3

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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-BOC-6-甲基吲哚 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 二碳酸二叔丁酯 、 水 、 碳酸氢钠 、 二甲基亚砜 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 氘代苯 为溶剂， 反应 12.92h， 生成 吲哚-6-甲醛
  参考文献：
  名称：

  6-（氟甲基）吲哚和6-（二氟甲基）吲哚的合成与反应性

  摘要：

  制备了由N-1 BOC保护的6-（氟甲基）吲哚和6-（二氟甲基）吲哚的前体，并通过快速真空热解脱保护。已经表征了这些新制备的未保护的吲哚衍生物的稳定性，并将其与先前已知的化合物6-（三氟甲基）吲哚的稳定性进行了比较。

  DOI：

  10.1016/s0040-4039(01)93319-2
• 作为产物：
  描述：

  6-甲基吲哚 生成 1-BOC-6-甲基吲哚
  参考文献：
  名称：

  Heterocyclyl-substituted dihydroquinazolines and their use as antiviral agents

  摘要：

  这项发明涉及公式（I）的杂环基取代的二氢喹唑啉，以及它们的制备方法、含有它们的药物，以及用于治疗和/或预防疾病的方法，特别是作为抗病毒剂，特别是针对巨细胞病毒。

  公开号：

  US20070185121A1

文献信息

• Cu-Catalyzed Oxidation of C2 and C3 Alkyl-Substituted Indole via Acyl Nitroso Reagents
  作者：Jun Zhang、Saeedeh Torabi Kohlbouni、Babak Borhan

  DOI：10.1021/acs.orglett.8b03185

  日期：2019.1.4

  The selective oxidation of C2-alkyl-substituted indoles to 3-oxindole and the selective C–H oxygenation or amination of C2,C3-dialkyl-substituted indoles at C2 are reported under mild conditions. The position of the alkyl substitution on the indole directs the reaction to different pathways under similar conditions.

  据报道，在温和的条件下，C2-烷基取代的吲哚被选择性氧化为3-羟吲哚，以及在C2处对C2，C3-二烷基取代的吲哚进行选择性的CH氧化或胺化。吲哚上烷基的取代位置将反应引导至相似条件下的不同途径。
• An entry to 2-(cyclobut-1-en-1-yl)-1<i>H</i>-indoles through a cyclobutenylation/deprotection cascade
  作者：Philipp Natho、Zeyu Yang、Lewis A. T. Allen、Juliette Rey、Andrew J. P. White、Philip J. Parsons

  DOI：10.1039/d1ob00430a

  日期：——

  A transition-metal-free methodology for the synthesis of 2-(cyclobut-1-en-1-yl)-1H-indoles through a cyclobutenylation/deprotection cascade was developed and the underlying mechanism was studied.

  通过环丁烯基化/脱保护串联反应合成2-(环丁-1-烯-1-基)-1H-吲哚的过渡金属自由方法已经开发，并研究了其中的机理。
• Tandem copper-catalysed aryl and alkenyl amination reactions: the synthesis of N-functionalised indoles
  作者：Roy C. Hodgkinson、Jurgen Schulz、Michael C. Willis

  DOI：10.1039/b817254d

  日期：——

  A Cu-diamine complex effectively catalyses tandem C–N bond formation on 2-(2-haloalkenyl)-aryl halide substrates, to deliver a series of N-functionalised indoles. Anilines, amides and carbamates are all effective coupling partners under the developed conditions.

  一个铜-双胺复合物有效催化了在2-(2-卤代烯基)-芳基卤化物底物上的串联C–N键形成，生成了一系列N功能化的吲哚。在优化的条件下，苯胺、酰胺和碳酸酯都是有效的偶联反应伙伴。
• Gold-catalyzed stereoselective dearomatization/metal-free aerobic oxidation: access to 3-substituted indolines/oxindoles
  作者：Kai Liu、Guangyang Xu、Jiangtao Sun

  DOI：10.1039/c7sc04086e

  日期：——

  excellent Z-selectivity, demonstrating unusual reactivity and selectivity compared with other noble metal catalysis. Importantly, simply followed by silica gel adsorption, an unprecedented metal-free aerobic oxidation occurs for indoles bearing N-electron donating substituents, providing a novel and efficient approach towards 3-substituted indolin-2-ones with a newly formed quaternary stereocenter in

  已经通过阳离子金（I）催化开发了重氮化合物使吲哚空前的脱芳香化作用。功能化选择性地发生在C3位置，以高收率和优异的Z传递亚甲基吲哚衍生物-选择性，与其他贵金属催化相比，显示出不同寻常的反应性和选择性。重要的是，简单地进行硅胶吸附之后，带有N电子给体取代基的吲哚会发生前所未有的无金属需氧氧化，从而为新颖的季铵立体中心具有优异立体选择性的3-取代的吲哚-2-酮提供了一种新颖而有效的方法。 。值得注意的是，这些方法提供了从丰富的原料化学物质中直接和选择性地获得各种有价值的中间体的途径。
• Structure–Activity Relationship (SAR) Optimization of 6-(Indol-2-yl)pyridine-3-sulfonamides: Identification of Potent, Selective, and Orally Bioavailable Small Molecules Targeting Hepatitis C (HCV) NS4B
  作者：Nanjing Zhang、Xiaoyan Zhang、Jin Zhu、Anthony Turpoff、Guangming Chen、Christie Morrill、Song Huang、William Lennox、Ramesh Kakarla、Ronggang Liu、Chunshi Li、Hongyu Ren、Neil Almstead、Srikanth Venkatraman、F. George Njoroge、Zhengxian Gu、Valerie Clausen、Jason Graci、Stephen P. Jung、Yingcong Zheng、Joseph M. Colacino、Fred Lahser、Josephine Sheedy、Anna Mollin、Marla Weetall、Amin Nomeir、Gary M. Karp

  DOI：10.1021/jm401621g

  日期：2014.3.13

  an acceptable pharmacokinetic profile. Compound 4t has excellent potency against the HCV 1b replicon, with an EC50 = 2 nM and a selectivity index of >5000 with respect to cellular GAPDH. Compound 4t has an overall favorable pharmacokinetic profile with oral bioavailability values of 62%, 78%, and 18% in rats, dogs, and monkeys, respectively, as well as favorable tissue distribution properties with a

  一种新型的，靶向NS4B丙型肝炎RNA复制的强效，和口服生物抑制剂，化合物4吨（PTC725），已经通过6-（吲哚-2-基）的化学优化吡啶-3-磺酰胺标识2，以改善DMPK和安全特性。SAR研究的重点是确定吲哚N-1，C-5和C-6位置的取代基与磺酰胺基的最佳组合，以限制体内氧化代谢的潜力并达到可接受的药代动力学轮廓。化合物4t具有抗HCV 1b复制子的出色效能，相对于细胞GAPDH ，EC 50 = 2 nM，选择性指数> 5000。复合4t 具有总体良好的药代动力学特征，大鼠，狗和猴子的口服生物利用度分别为62％，78％和18％，并且大鼠的肝血浆接触比为25，具有良好的组织分布特性。