5-溴-3-甲酰基吲哚-1-羧酸叔丁酯 | 325800-39-3

• 物质功能分类: 医药中间体 - 杂环化合物 - 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: 5-溴-3-甲酰基吲哚-1-羧酸叔丁酯
• 英文名称: tert-butyl 5-bromo-3-formyl-1H-indole-1-carboxylate
• 英文别名: 1-Boc-5-Bromo-3-formylindole；tert-butyl 5-bromo-3-formylindole-1-carboxylate
• CAS: 325800-39-3
• 化学式: C₁₄H₁₄BrNO₃
• 分子量: 324.174
• InChiKey: SESUUKNLBXWLAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  426.7±48.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-BOC-5-Bromo-3-formylindole
Synonyms: t-Butyl 5-bromo-3-formylindole-1-carboxylate; 1-Boc-5-bromoindole-3-carboxaldehyde

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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-5-Bromo-3-formylindole
CAS number: 325800-39-3

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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: C14H14BrNO3
Molecular weight: 324.2

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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, hydrogen bromide.

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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：

  5-溴-3-甲酰基吲哚-1-羧酸叔丁酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以96%的产率得到5-溴吲哚-3-甲醛
  参考文献：
  名称：

  简单且选择性地去除吲哚、吡咯、吲唑和咔啉上的叔丁氧羰基 (Boc) 保护基团

  摘要：

  摘要 使用催化量的 NaOMe 作为碱在无水 MeOH 中，以高产率实现了吲哚、吡咯、吲唑和咔啉上的 N-叔丁氧基羰基 (N-Boc) 基团的高选择性和高效脱保护，在环境温度。IICT 通讯编号 060512。

  DOI：

  10.1080/00397910601033724
• 作为产物：
  描述：

  5-溴吲哚 在 4-二甲氨基吡啶 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 5-溴-3-甲酰基吲哚-1-羧酸叔丁酯
  参考文献：
  名称：

  吲哚和螺吲哚植物抗毒素新的5-溴衍生物的合成

  摘要：

  亲电子芳族取代是有机化学中最深入研究的反应之一。在本文中，通过在各种溴化剂存在下亲电取代吲哚啉在C-5位置的芳族核，获得了5溴化螺螺芥子醇甲基醚VII，VIII。按照由二氢吲哚合成1-甲氧基螺芥菜籽油甲基醚（V）的顺序，也由5-溴吲哚（IX）制备相同的产物。此外，新的相关5-溴螺吲哚啉衍生物XX–XXIII合成了它们，并检查了它们对人肿瘤细胞系的生物学活性。在C-5位置的吲哚或二氢吲哚骨架中存在溴会导致对白血病细胞系（Jurkat，CEM）的抗癌活性部分提高。新制备的产品的结构通过1 H和13 C NMR光谱测定，包括HSQC，HMBC，COSY，NOESY和DEPT测量。

  DOI：

  10.1515/chempap-2015-0230

文献信息

• Metal-Free Trifluoromethylation of Aromatic and Heteroaromatic Aldehydes and Ketones
  作者：Yupu Qiao、Tuda Si、Ming-Hsiu Yang、Ryan A. Altman

  DOI：10.1021/jo501289v

  日期：2014.8.1

  derivatives under mild conditions remains an important goal for medicinal and agricultural chemists. One representative example of a desirable transformation involves the conversion of aromatic and heteroaromatic ketones and aldehydes into aryl and heteroaryl β,β,β-trifluoroethylarenes and -heteroarenes. The traditional approach for this net transformation involves stoichiometric metals and/or multistep reaction

  在温和条件下将简单和常见的底物转化为氟烷基衍生物的能力仍然是医药和农业化学家的一个重要目标。理想转化的一个代表性实例包括将芳族和杂芳族酮和醛转化为芳基和杂芳基β,β,β-三氟乙基芳烃和-杂芳烃。这种净转化的传统方法涉及化学计量的金属和/或多步反应序列，它们消耗过多的时间、材料和劳动力资源，同时提供低产率的产品。为了补充这些传统策略，我们报告了一种一锅式无金属脱羧程序，用于从容易获得的酮和醛中获取 β,β,β-三氟乙基芳烃和 - 杂芳烃。这种方法有几个好处，
• One‐Pot Oxidation of Secondary Alcohols to <i>α</i> ‐Hydroxy Ketones: Application to Synthesis of Oxoaplysinopsin D, E, F, &amp; G
  作者：Akshay S. Kulkarni、Eagala Ramesh、D. Srinivasa Reddy

  DOI：10.1002/ejoc.202100184

  日期：2021.4.22

  A one‐pot method for the transformation of secondary alcohols to α‐hydroxy ketones using pyridinium dichromate (PDC) at room temperature is described. The method was tested with a variety of hydantoin derivatives. As a direct application, total synthesis of four natural oxoaplysinopsins D, E, F and G was accomplished for the first time through a common dihydroxy intermediate.

  描述了一种在室温下使用重铬酸吡啶鎓（PDC）将仲醇转化为α-羟基酮的一锅法。用多种乙内酰脲衍生物测试了该方法。作为直接的应用，四种天然的氧代皂甙酶D，E，F和G的全合成是通过共同的二羟基中间体首次完成的。
• Three-Component One-Pot Synthesis of 3-(2-Furanyl)indoles from Acetylenedicarboxylate, Isocyanide, and 3-Formylindole
  作者：B. Reddy、A. Reddy、D. Somashekar、J. Yadav、B. Sridhar

  DOI：10.1055/s-0029-1218824

  日期：2010.8

  The zwitterions derived from isocyanide and dimethyl acetylenedicarboxylate undergo smooth condensation with 3-formylindoles in benzene at room temperature to give the corresponding 3-(2-furanyl)indoles in good yields. This method provides a simple and convenient route to produce a wide range of 3-heteroarylindoles in a one-pot operation.

  来自异氰和二甲基乙炔二羧酸酯的半缩醛与3-甲醛基吲哚在室温下的苯溶液中顺利进行缩合反应，以良好产率得到相应的3-(2-呋喃基)吲哚。此方法提供了一种简单方便的途径，通过一锅法操作制备多种3-杂芳基吲哚。
• 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。
• One-pot sequential multicomponent reaction between <i>in situ</i> generated aldimines and succinaldehyde: facile synthesis of substituted pyrrole-3-carbaldehydes and applications towards medicinally important fused heterocycles
  作者：Anoop Singh、Nisar A. Mir、Sachin Choudhary、Deepika Singh、Preetika Sharma、Rajni Kant、Indresh Kumar

  DOI：10.1039/c8ra01637b

  日期：——

  An efficient sequential multi-component method for the synthesis of N-arylpyrrole-3-carbaldehydes has been developed. This reaction involved a proline-catalyzed direct Mannich reaction-cyclization sequence between succinaldehyde and in situ generated Ar/HetAr/indolyl-imines, followed by IBX-mediated oxidative aromatization in one-pot operation. The practical utility of this procedure is shown at gram-scale

  开发了一种有效的连续多组分合成N-芳基吡咯-3-甲醛的方法。该反应涉及琥珀醛和原位生成的 Ar/HetAr/吲哚基亚胺之间脯氨酸催化的直接曼尼希反应环化序列，然后在一锅操作中进行 IBX 介导的氧化芳构化。该方法的实用性以克级显示，并合成了多种生物活性稠合杂环支架，例如吡咯并喹啉、吡咯并恶二唑、二氢吡咯并喹啉和吡咯并菲啶。