5-氰基芦竹碱 | 25514-67-4

• 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-氰基芦竹碱
• 英文名称: 3-Dimethylaminomethylindole-5-carbonitrile
• 英文别名: 5-cyano-3-(dimethylamino)methyl-1H-indole；5-cyanogramine；3-[(dimethylamino)methyl]-1H-indole-5-carbonitrile
• CAS: 25514-67-4
• 化学式: C₁₂H₁₃N₃
• mdl: MFCD01719098
• 分子量: 199.255
• InChiKey: JOPBIDDQPQFQHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 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-Cyanogramine
Synonyms: 3-[(Dimethylamino)methyl]-1H-indole-5-carbonitrile

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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-Cyanogramine
CAS number: 25514-67-4

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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: C12H13N3
Molecular weight: 199.3

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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：

  5-氰基芦竹碱 在 sodium iodide 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 氯仿 、 乙酸乙酯 为溶剂， 生成 Methyl-5-cyanoindole-3-propionate
  参考文献：
  名称：

  Antimigraine 4-pyrimidinyl and pyridinyl derivatives of

  摘要：

  一系列新颖的Formula I的吲哚-3-基烷基哌嗪的烷氧基吡啶-4-基和烷氧基吡啶-4-基衍生物旨在成为有用的药剂，用于缓解血管性头痛，基于它们在5-HT1D结合位点的强亲和力和激动剂活性。

  公开号：

  US05434154A1
• 作为产物：
  描述：

  5-氰基吲哚 在 Merrifield resin bound glycerol 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 78.0h， 生成 5-氰基芦竹碱
  参考文献：
  名称：

  Kraxner, Johannes; Arlt, Michael; Gmeiner, Peter, Synlett, 2000, # 1, p. 125 - 127

  摘要：

  DOI：

文献信息

• 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。
• Molecular iodine mediated oxidative cleavage of the C–N bond of aryl and heteroaryl (dimethylamino)methyl groups into aldehydes
  作者：Ketan S. Mandrekar、Santosh G. Tilve

  DOI：10.1039/d0nj05832g

  日期：——

  The oxidative cleavage of the C–N bond of aryl and heteroaryl (dimethylamino)methyl groups is achieved by employing molecular iodine as a mild oxidizing agent under ambient conditions in the presence of a mild base. The important reaction of C3 formylation of free NH and substituted indoles containing various substituents is accomplished from the corresponding Mannich bases. This methodology can also

  芳基和杂芳基（二甲基氨基）甲基的C–N键的氧化裂解可通过在环境条件下，弱碱存在下使用分子碘作为弱氧化剂来实现。游离NH和含有各种取代基的取代的吲哚的C 3甲酰化的重要反应是由相应的曼尼希碱完成的。该方法还可以扩展为芳基和其他杂芳基醛和酮的合成。此外，该方法的实用性已成功以克为单位进行了证明。
• Indolylalkyl derivatives of pyrimidinylpiperazine for treating vascular
  申请人：Bristol-Myers Squibb Company

  公开号：US05300506A1

  公开（公告）日：1994-04-05

  A series of novel indol-3-ylalkyl derivatives of alkoxypyrimidinylpiperazines are disclosed as Formula I. ##STR1## These compounds are intended to be useful agents for alleviation of vascular headache on the basis of their potent affinity and agonist activity at 5-HT1D binding sites.

  一系列新颖的吲哚-3-基烷基衍生物的烷氧基嘧啶基哌嗪被披露为公式I。这些化合物旨在通过它们在5-HT1D结合位点的强亲和力和激动剂活性来缓解血管性头痛。
• INDOLYLALKYL DERIVATIVES OF PYRIMIDINYLPIPERAZINE AND METABOLITES THEREOF FOR TREATMENT OF ANXIETY, DEPRESSION, AND SEXUAL DYSFUNCTION
  申请人：KRAMER Stephen J.

  公开号：US20090281114A1

  公开（公告）日：2009-11-12

  The present invention relates to a method for alleviation, prevention, and treatment of anxiety, depression, and sexual dysfunction by administering certain indolylalkyl derivatives of pyrimidinylpiperazine or metabolites thereof. A preferred embodiment is of the following formula:

  本发明涉及通过给予某些吡咯啉基吡咯嗪的衍生物或其代谢物来缓解、预防和治疗焦虑、抑郁和性功能障碍的方法。一种首选实施例的化学式如下：
• 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。