1-BOC-吲哚-4-羧酸甲酯 | 220499-11-6

• 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-4-羧酸甲酯
• 英文名称: 1-(tert-butyl) methyl 1H-1,4-indoledicarboxylate
• 英文别名: indole-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester；1-(tert-butyl) 4-methyl 1H-1,4-indoledicarboxylate；1-tert-Butyl 4-methyl 1H-indole-1,4-dicarboxylate；1-O-tert-butyl 4-O-methyl indole-1,4-dicarboxylate
• CAS: 220499-11-6
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: HLGNJZVTHXMEHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 1-BOC-indole-4-carboxylate
Synonyms: 1-tert-Butyl 4-methyl 1H-indole-1,4-dicarboxylate

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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: Methyl 1-BOC-indole-4-carboxylate
CAS number: 220499-11-6

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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: C15H17NO4
Molecular weight: 275.3

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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-吲哚-4-羧酸甲酯 在 lithium hydroxide 、 正丁基锂 、 水 、 三溴化磷 、 二异丁基氢化铝 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 14.34h， 生成 (2S)-2-amino-3-<1-(tert-butoxycarbonyl)-1H-4-indolyl>propanoic acid
  参考文献：
  名称：

  Synthesis of (2S)-2-amino-3-(1H-4-indolyl)propanoic acid, a novel tryptophan analog for structural modification of bioactive peptides

  摘要：

  A convenient, multigram synthesis of a never alpha-amino acid (2S)-2-amino-3-(1H-4-indolyl)propanoic acid (la), is reported. An Fmoc-t-Boc derivative of this novel regioisomer of the natural aromatic amino acid tryptophan could be readily incorporated into bioactive synthetic peptides using standard solid phase synthesis. The synthesis featured the use of Schollkopf chiral auxiliary reagents for chirality induction during a key step. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00445-5
• 作为产物：
  描述：

  2-甲基-3-硝基苯甲酸 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 potassium hydrogencarbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 25.0~120.0 ℃ 、379.21 kPa 条件下， 反应 48.0h， 生成 1-BOC-吲哚-4-羧酸甲酯
  参考文献：
  名称：

  Synthesis of (2S)-2-amino-3-(1H-4-indolyl)propanoic acid, a novel tryptophan analog for structural modification of bioactive peptides

  摘要：

  A convenient, multigram synthesis of a never alpha-amino acid (2S)-2-amino-3-(1H-4-indolyl)propanoic acid (la), is reported. An Fmoc-t-Boc derivative of this novel regioisomer of the natural aromatic amino acid tryptophan could be readily incorporated into bioactive synthetic peptides using standard solid phase synthesis. The synthesis featured the use of Schollkopf chiral auxiliary reagents for chirality induction during a key step. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00445-5

文献信息

• [EN] BIPHENYL SUBSTITUTED 1,3-DIHYDRO-BENZOIMIDAZOL-2-YLIDENEAMINE DERIVATIVES<br/>[FR] DÉRIVÉS DE 1,3-DIHYDRO-BENZOIMIDAZOL-2-YLIDÈNE-AMINE À SUBSTITUTION BIPHÉNYLE
  申请人：NOVARTIS AG

  公开号：WO2011157787A1

  公开（公告）日：2011-12-22

  The invention relates to new derivatives of formula (I), wherein the substituents are as defined in the specification; to processes for the preparation of such derivatives; pharmaceutical compositions comprising such derivatives; such derivatives as a medicament; such derivatives for the treatment of one or more IGF-1 R mediated disorders or diseases.

  这项发明涉及公式（I）的新衍生物，其中取代基如规范中所定义；制备这种衍生物的方法；包括这种衍生物的药物组合物；将这种衍生物用作药物；将这种衍生物用于治疗一个或多个IGF-1 R介导的疾病。
• [EN] PIPERIDINYL SUBSTITUTED 1,3-DIHYDRO-BENZOIMIDAZOL-2-YLIDENEAMINE DERIVATIVES<br/>[FR] DÉRIVÉS DE 1,3-DIHYDRO-BENZOIMIDAZOL-2-YLIDÈNE-AMINE À SUBSTITUTION PIPÉRIDINYLE
  申请人：NOVARTIS AG

  公开号：WO2011157793A1

  公开（公告）日：2011-12-22

  The invention relates to new derivatives of formula (I) wherein the substituents are as defined in the specification; to processes for the preparation of such derivatives; pharmaceutical compositions comprising such derivatives; such derivatives as a medicament; such derivatives for the treatment of one or more IGF-1R mediated disorders or diseases.

  该发明涉及公式（I）的新衍生物，其中取代基如规范中定义；制备这种衍生物的方法；包含这种衍生物的药物组合物；这种衍生物作为药物；这种衍生物用于治疗一个或多个IGF-1R介导的疾病或疾病。
• Electrochemical Dearomative Dicarboxylation of Heterocycles with Highly Negative Reduction Potentials
  作者：Yong You、Wataru Kanna、Hideaki Takano、Hiroki Hayashi、Satoshi Maeda、Tsuyoshi Mita

  DOI：10.1021/jacs.1c13032

  日期：2022.3.2

  CO2 radical anion (E1/2 of CO2 = −2.2 V in DMF and −2.3 V in CH3CN vs SCE) that produces unprecedented trans-oriented 2,3-dicarboxylic acids from N-Ac-, Boc-, and Ph-protected indoles that exhibit highly negative reduction potentials (−2.50 to −2.94 V). On the basis of the calculated reduction potentials, N-protected indoles with reduction potentials up to −3 V smoothly undergo the desired dicarboxylation

  使用 CO 2对稳定的杂芳烃进行脱芳族二羧基化具有很高的挑战性，但它代表了一种非常有效的生产合成有用二羧酸的方法，二羧酸有可能用作生物活性分子（如天然产物和药物先导物）的中间体。然而，这些类型的转化仍然不发达，高效的简明方法（例如，高产率和高选择性的二羧基化）尚未见报道。我们在此描述了一种使用 CO 2自由基阴离子（ DMF 中的E 1/2的 CO 2 = -2.2 V 和 CH 3 CN vs SCE 中的 -2.3 V）的新电化学方案，该方案产生前所未有的反式来自N -Ac-、Boc- 和 Ph-保护的吲哚的取向 2,3-二羧酸，具有高负还原电位（-2.50 至 -2.94 V）。基于计算的还原电位，还原电位高达-3 V的N-保护吲哚顺利地进行了所需的二羧化。其他杂芳烃，包括苯并呋喃、苯并噻吩、缺电子呋喃、噻吩、1,3-二苯基异苯并呋喃和N-Boc-吡唑，也表现出比 -3 V 更正的还
• Neo-tryptophan
  申请人：Mayo Foundation for Medical Education And Research

  公开号：US06214790B1

  公开（公告）日：2001-04-10

  The invention provides a novel amino acid, neo-tryptophan, as well as polypeptides containing this novel amino acid such as neurotensin analogs. In addition, the invention provides neo-tryptophan derivatives, serotonin-like neo-tryptophan derivatives, and polypeptides containing such derivatives. The invention also provides methods for making neo-tryptophan, neo-tryptophan derivatives, serotonin-like neo-tryptophan derivatives, and compositions containing these compounds. Further, the invention provides methods for inducing a neurotensin response in a mammal as well as methods for treating a mammal having a serotonin recognition molecule.

  该发明提供了一种新型氨基酸neo-色氨酸，以及含有该新型氨基酸的多肽，如神经肽类似物。此外，该发明提供了neo-色氨酸衍生物、类似于5-羟色胺的neo-色氨酸衍生物，以及含有这些衍生物的多肽。该发明还提供了制备neo-色氨酸、neo-色氨酸衍生物、类似于5-羟色胺的neo-色氨酸衍生物以及含有这些化合物的组合物的方法。此外，该发明提供了诱导哺乳动物神经肽反应的方法，以及治疗具有5-羟色胺识别分子的哺乳动物的方法。
• Indazole compounds
  申请人：Ericsson M. Anna

  公开号：US20070282101A1

  公开（公告）日：2007-12-06

  Novel compounds of Formula (I) or pharmaceutically acceptable salts, prodrugs and biologically active metabolites thereof of Formula (I) wherein the substituents are as defined herein, which are useful as therapeutic agents.

  本发明提供了化合物(I)或其药学上可接受的盐、前药和生物活性代谢物，其中取代基如定义所述，这些化合物可用作治疗剂。