1-Boc-吲哚 | 75400-67-8

• 物质功能分类: 医药中间体 - 吲哚类化合物
• 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-吲哚
• 中文别名: 1-BOC-吲哚/1H-吲哚-1-羧酸叔丁酯；1-吲哚羧酸叔丁酯；1H-吲哚-1-羧酸叔丁酯；1-N-Boc-吲哚；1-BOC-吲哚
• 英文名称: indole-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 1H-indole-1-carboxylate；N-Boc indole；1-Boc-indole；tert-butyl indole-1-carboxylate
• CAS: 75400-67-8
• 化学式: C₁₃H₁₅NO₂
• mdl: MFCD02093939
• 分子量: 217.268
• InChiKey: OWPIFQXNMLDXKW-UHFFFAOYSA-N

物化性质

• 熔点：
  24-26
• 沸点：
  201 °C(lit.)
• 密度：
  1.07 g/mL at 25 °C(lit.)
• 闪点：
  160 °F
• 稳定性/保质期：

  远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT, KEEP COLD
• 危险品标志：
  Xi
• WGK Germany：
  3
• 海关编码：
  2933990090
• 安全说明：
  S24/25
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302,H317
• 储存条件：
  存放在密封容器中，并放置在阴凉、干燥处。储存地点须远离氧化剂。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: tert-Butyl 1H-indole-1-carboxylate
Synonyms: 1-Boc-indole

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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: tert-Butyl 1H-indole-1-carboxylate
CAS number: 75400-67-8

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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.

---

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: C13H15NO2
Molecular weight: 217.3

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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.

---

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-吲哚 在 碘 、 叔丁基锂 、 sodium methylate 、 正戊烷 、 碘甲烷 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.92h， 生成 2-(2-iodo-1H-indol-3-yl)acetonitrile
  参考文献：
  名称：

  2-碘色胺和2-碘-5-甲氧基色胺的制备

  摘要：

  描述了吲哚和5-甲氧基吲哚的区域特异性碘化，以及将这些2-碘吲哚合成为相应的色胺的方法。

  DOI：

  10.1002/jhet.5570220260
• 作为产物：
  描述：

  2-氨基苯乙醇 在 二(氰基苯)二氯化钯 、 亚硝酸特丁酯 、 氧气 、 三乙胺 、 potassium hydroxide 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 180.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 生成 1-Boc-吲哚
  参考文献：
  名称：

  Pd-tBuONO共催化好氧吲哚合成

  摘要：

  甲的Pd-吨作为终端氧化剂被显影BUONO共催化的分子氧吲哚的可扩展性和实用的合成。在一种通用条件下，末端或内部2乙烯基苯胺均可顺利转化为所需的吲哚。吲哚美辛和潜在的抗乳腺癌候选药物1的大规模合成已对该方法进行了评估。

  DOI：

  10.1002/adsc.201701512
• 作为试剂：
  描述：

  2-丙烯酰胺,N-(2-碘苯基)-2-甲基- 在 palladium diacetate 、 三苯基膦 三乙基硼 、 叔丁基锂 、 1-Boc-吲哚 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 1,3,3-三甲基-2,3-二氢-1H-吲哚-2-酮
  参考文献：
  名称：

  A palladium-catalyzed tandem cyclization-cross-coupling reaction using indolylborate as a transfer agent

  摘要：

  Investigation of the palladium-catalyzed tandem cyclization-cross-coupling reaction using indolylborate (2) as a transfer agent has been carried out. Furthermore, the cross-coupling reaction performed under carbon monoxide led to the generation of indolyl ketones. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.065

文献信息

• Gold(<scp>i</scp>)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes
  作者：Manjur O. Akram、Popat S. Shinde、Chetan C. Chintawar、Nitin T. Patil

  DOI：10.1039/c8ob00630j

  日期：——

  Gold(I)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes are described. This redox neutral strategy offers an efficient approach to diverse biaryls, vinyl arenes and arylacetylenes. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the in situ formation of Ph3PAuIR (R = aryl, vinyl and alkynyl) species which is crucial for the activation of aryldiazonium

  描述了金（I）催化的芳基重氮盐与有机锡烷的交叉偶联反应。这种氧化还原中性策略为各种联芳基，乙烯基芳烃和芳基乙炔提供了一种有效的方法。用NMR和ESI-MS监测反应为原位形成Ph 3 PAu I R（R =芳基，乙烯基和炔基）物种提供了有力证据，这对于激活芳基重氮盐至关重要。
• Catalyst-free, scalable heterocyclic flow photocyclopropanation
  作者：Viktor Klöpfer、Robert Eckl、Johannes Floß、Philippe M. C. Roth、Oliver Reiser、Joshua P. Barham

  DOI：10.1039/d1gc01624e

  日期：——

  have been limited by their explosivity and toxicity. Their catalyst-free photolysis in continuous flow improves safety, sustainability and scalability compared to batch reactions. Herein, we report the continuous flow catalyst-free photocyclopropanation of heterocycles in up to grams per h productivity in a non-chlorinated, biodegradable solvent. Highly-functionalized cyclopropanated products are key

  工业过程开发受多种因素驱动，包括安全性、成本、稳健性和环境方面。然而，在化学工业中建立芳基重氮酯的尝试由于其爆炸性和毒性而受到限制。与间歇反应相比，它们在连续流动中的无催化剂光解提高了安全性、可持续性和可扩展性。在此，我们报告了在非氯化、可生物降解的溶剂中以高达每小时克的生产率连续流动无催化剂的杂环光环丙烷化反应。高度官能化的环丙烷化产物是合成药物和药学相关化合物的关键中间体。通过实验设计方法获得最佳条件和过程理解。与大规模批量实验相比，连续流动条件提高了产量、生产率和过程安全性。
• Novel organophosphorus derivatives of indazoles and use thereof as medicinal products
  申请人：Cherrier Marie-Pierre

  公开号：US20050137171A1

  公开（公告）日：2005-06-23

  The present invention relates in particular to novel chemical compounds, particularly to novel organophosphorus derivatives of indazoles, to the compositions containing them, and to the use thereof as medicinal products for treating cancers.

  本发明特别涉及新型化合物，特别是吲唑的新型有机磷衍生物，包含它们的组合物，以及将其用作治疗癌症的药物产品。
• Enantioselective Formal [4+2] Cycloadditions to 3-Nitroindoles by Trienamine Catalysis: Synthesis of Chiral Dihydrocarbazoles
  作者：Yang Li、Fernando Tur、Rune Pagh Nielsen、Hao Jiang、Frank Jensen、Karl Anker Jørgensen

  DOI：10.1002/anie.201509693

  日期：2016.1.18

  enantioselective formal [4+2] cycloadditions of 3‐nitroindoles are presented. By using 3‐nitroindoles in combination with an organocatalyst, chiral dihydrocarbazole scaffolds are formed in moderate to good yields (up to 87 %) and enantioselectivities (up to 97 % ee). The reaction was extended to include enantioselective [4+2] cycloadditions of 3‐nitrobenzothiophene. The reaction proceeds through a [4+2] cycl

  提出了第一个3-硝基吲哚的对映选择性形式[4 + 2]环加成反应。通过将3-硝基吲哚与有机催化剂结合使用，可以形成中等至良好的收率（高达87％）和对映选择性（高达97％ee）的手性二氢咔唑支架。反应扩展到包括3-硝基苯并噻吩的对映选择性[4 + 2]环加成反应。反应在温和的反应条件下通过[4 + 2]环加成/消除级联进行。此外，提出了对映体富集的对映体的环加合物的非对映选择性还原。基于实验和计算研究，讨论了反应机理。
• N-2-嘧啶基-3-氟吲哚类化合物及其制备方法与应用
  申请人：浙江工业大学

  公开号：CN112574180A

  公开（公告）日：2021-03-30

  一种式(I)所示的N‑2‑嘧啶基‑3‑氟吲哚类化合物的制备方法，所述的方法包括以下步骤：以乙腈溶剂为反应介质，加入式(III)所示N‑2‑嘧啶基吲哚类化合物、selectfluor、CuI和光催化剂，在蓝光照射下室温反应2～5h，反应完全后，所得反应混合物经后处理得到式(I)所示的N‑2‑嘧啶基‑3‑氟吲哚类化合物。该类化合物是一种具有显著抑制单胺氧化酶活性的抑制剂类化合物，特别是I‑2和I‑3对MAO‑A具有较高选择性，为抗抑郁，抗帕金森类药物筛选提供了研究基础。本发明利用光催化剂，在蓝光照射和室温下进行反应，反应条件温和、位点选择性高，反应高效，绿色，环保，反应收率可达到85％。