5-氟芦竹碱 | 343-90-8

• 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-氟芦竹碱
• 英文名称: 1-(5-fluoro-1H-indol-3-yl)-N,N-dimethylmethanamine
• 英文别名: 3-dimethylaminomethyl-5-fluoroindole
• CAS: 343-90-8
• 化学式: C₁₁H₁₃FN₂
• mdl: MFCD00022731
• 分子量: 192.236
• InChiKey: QNCNSISRJMCGPK-UHFFFAOYSA-N

物化性质

• 熔点：
  145-149°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 安全说明：
  S22,S24/25
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  | 2-8°C |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Fluorogramine
Synonyms:

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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: 5-Fluorogramine
CAS number: 343-90-8

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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.

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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: C11H13FN2
Molecular weight: 192.2

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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 fluoride.

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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

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  5-氟吲哚-3-乙腈	2-(5-fluoro-1H-indol-3-yl)acetonitrile	73139-85-2	C10H7FN2	174.177
  ——	bis(5-fluoro-1H-indol-3-yl)methane	215997-93-6	C17H12F2N2	282.292
  5-氟吲哚-3-乙酸	(5-fluoroindol-3-yl)acetic acid	443-73-2	C10H8FNO2	193.177
  5-氟-DL-色氨酸	DL-5-fluorotryptophan	154-08-5	C11H11FN2O2	222.219
  5-氟-L-色氨酸	5-fluoro-L-tryptophan	16626-02-1	C11H11FN2O2	222.219
  2-氨基-3-(5-氟-1H-吲哚-3-基)-丙酸甲酯	5-fluoro-DL-tryptophan	171489-71-7	C12H13FN2O2	236.246
  ——	ethyl 2-amino-3-(5-fluoro-1H-indol-3-yl)propanoate	——	C13H15FN2O2	250.273

反应信息

• 作为反应物：
  描述：

  5-氟芦竹碱 在 盐酸 、 sodium hydride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 mineral oil 为溶剂， 反应 2.0h， 生成 5-氟-DL-色氨酸
  参考文献：
  名称：

  紫罗兰色杆菌中紫堇青素的生物合成，1-色氨酸氧化酶VioA的结构和功能。

  摘要：

  紫罗兰素是紫罗兰色杆菌的天然紫色颜料，具有潜在的医学应用，如抗微生物，抗病毒和抗癌药。紫胶素生物合成的第一步是通过黄酮酶L-色氨酸氧化酶（VioA）将L-色氨酸氧化转化为相应的α-亚胺。与底物相关的（3-（1H-吲哚-3-基）-2-甲基丙酸）和与产品相关的（2-（1H-吲哚-3-基甲基）丙-2-烯酸）竞争性VioA抑制剂是合成用于后续的动力学和X射线晶体学研究。解析了二元VioA·FADH2和三元VioA·FADH2·2-（1H-吲哚-3-基甲基）丙-2-烯酸配合物的结构。VioA形成“松散相关”的同型二聚体，如小角度X射线散射实验所示。根据结构保守的辅因子结合结构域，VioA属于FAD依赖性氧化还原酶的谷胱甘肽还原酶家族2。VioA的底物结合域主要负责l-色氨酸的特异性识别。其他典型的氨基酸被有效区分，只有少量的1-苯丙氨酸转化。此外，7-氮杂-色氨酸，1-甲基-色氨酸，5-甲基-色氨酸

  DOI：

  10.1074/jbc.m116.741561
• 作为产物：
  描述：

  5-氟吲哚-2-甲酸 在 溶剂黄146 作用下， 生成 5-氟芦竹碱
  参考文献：
  名称：

  Bergmann; Pelchowicz, Journal of the Chemical Society, 1959, p. 1913

  摘要：

  DOI：

文献信息

• [EN] NOVEL DUAL MODE OF ACTION SOLUBLE GUANYLATE CYCLASE ACTIVATORS AND PHOSPHODIESTERASE INHIBITORS AND USES THEREOF<br/>[FR] NOUVEAUX ACTIVATEURS DE LA GUANYLATE CYCLASE SOLUBLE À DOUBLE MODE D'ACTION ET INHIBITEURS DE PHOSPHODIESTÉRASE ET LEURS UTILISATIONS
  申请人：TOPADUR PHARMA AG

  公开号：WO2021245192A1

  公开（公告）日：2021-12-09

  The present invention relates to compounds of formula (I), or pharmaceutically acceptable salt, solvate or hydrate thereof, wherein said compound of formula (I) comprises at least one covalently bound -ONO2 or -ONO moiety and at most four covalently bound -ONO2 or -ONO moieties, and wherein AR, R1, X, R3 and R4 are as defined in claim 1; and pharmaceutical compositions thereof, and their use in methods of treating or preventing a disease alleviated by inhibition of PDE5 in a human or in a non-human mammal.

  本发明涉及式(I)的化合物，或其药学上可接受的盐、溶剂或水合物，其中所述式(I)的化合物至少包括一个共价结合的-ONO2或-ONO基团，最多包括四个共价结合的-ONO2或-ONO基团，其中AR、R1、X、R3和R4如权利要求1所定义；以及其药物组合物，以及它们在治疗或预防通过抑制人类或非人类哺乳动物中的PDE5而缓解的疾病的方法中的使用。
• Synthesis of tryptophans by alkylation of chiral glycine enolate equivalents with quaternary gramines
  作者：Matiss Reinfelds、Konstantins Kalinins、Dace Katkevica、Ronalds Zemribo、Martins Katkevics

  DOI：10.1016/j.tetlet.2015.09.017

  日期：2015.10

  source of the 3-methylindole fragment for diastereoselective alkylation. The best yields and stereoselectivity were obtained for the alkylation of a chiral William’s morpholinone enolate. Based on this transformation, a general method for the synthesis of enantiopure, indole ring substituted tryptophan derivatives was developed with good overall yields.

  发现季胺是非对映选择性烷基化的3-甲基吲哚片段的合适来源。对于手性William's吗啉代烯醇烯酸酯的烷基化，可获得最佳收率和立体选择性。基于该转化，开发了具有良好总收率的对映体纯的，吲哚环取代的色氨酸衍生物的合成的通用方法。
• Catalyst-Controlled Regiodivergence in Rearrangements of Indole-Based Onium Ylides
  作者：Vaishnavi N. Nair、Volga Kojasoy、Croix J. Laconsay、Wang Yeuk Kong、Dean J. Tantillo、Uttam K. Tambar

  DOI：10.1021/jacs.1c00283

  日期：2021.6.23

  metal-coordinated ion-pair in the copper catalyzed [1,2]-rearrangement that recombines in the solvent-cage. The application of our methodology was demonstrated in the first total synthesis of the indole alkaloid (±)-sorazolon B, which enabled the stereochemical reassignment of the natural product. Further functional group transformations of the rearrangement products to generate valuable synthetic intermediates

  我们开发了由吲哚底物衍生的鎓叶立德的催化剂控制区域发散重排。由取代的吲哚原位形成的氧鎓叶立德分别在铑和铜催化剂存在下选择性地进行[2,3]-和[1,2]-重排。实验和密度泛函理论 (DFT) 相结合的计算研究表明，不同的机制途径涉及铑催化反应中的无金属叶立德有利于 [2,3]-重排，以及铜催化反应中的金属配位离子对 [1 ,2]-在溶剂笼中重新组合的重排。我们的方法的应用在吲哚生物碱 (±)-sorazolon B 的首次全合成中得到了证明，这使得天然产物的立体化学重新分配成为可能。还展示了重排产物的进一步官能团转化以产生有价值的合成中间体。
• [EN] 3-AMINO CHOMAN AND 2-AMINO TETRALIN DERIVATIVES<br/>[FR] DERIVES 3-AMINO CHOMANE ET 2-AMINO TETRALINE
  申请人：WYETH CORP

  公开号：WO2005012291A1

  公开（公告）日：2005-02-10

  3-Amino chroman and 2-amino tetralin derivatives and compositions containing such compounds are disclosed. Methods of using the 3-amino chroman and 2-amino tetralin compounds and compositions containing such compounds in the treatment of serotonin disorders, such as depression and anxiety, are also disclosed.

  揭示了3-氨基色苷和2-氨基四氢萘衍生物以及含有这些化合物的组合物。还揭示了在治疗血清素失调症，如抑郁症和焦虑症中使用3-氨基色苷和2-氨基四氢萘化合物以及含有这些化合物的组合物的方法。
• Rhodium-Catalyzed Enantioselective Cyclization of 3-Allenyl-indoles: Access to Functionalized Tetrahydrocarbazoles
  作者：Christian P. Grugel、Bernhard Breit

  DOI：10.1021/acs.orglett.9b01721

  日期：2019.8.2

  A highly selective rhodium-catalyzed cyclization of tethered 3-allenylindoles is reported. In a smooth reaction, 1-vinyltetrahydrocarbazoles are obtained in excellent yields and enantioselectivities. Aside from a great functional group tolerance, this method requires neither the Schlenk technique nor the use of anhydrous solvents. Preliminary mechanistic investigations proved that the reaction proceeds

  报道了拴系的3-烯基吲哚的高选择性铑催化的环化。在平稳的反应中，以优异的产率和对映选择性获得了1-乙烯基四氢咔唑。除了对官能团的耐受性强之外，该方法既不需要Schlenk技术，也不需要使用无水溶剂。初步的机理研究证明，该反应通过中间形成的螺环吲哚胺进行，该螺环吲哚胺迅速经历酸催化的立体有规迁移。