2-苯基六亚甲基亚胺 | 3466-82-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 中文名称: 2-苯基六亚甲基亚胺
• 中文别名: 2-苯基氮杂烷；2-苯基氮杂环庚烷；2-苯基六氢氮杂卓
• 英文名称: 2-phenylazepane
• CAS: 3466-82-8
• 化学式: C₁₂H₁₇N
• mdl: MFCD02663698
• 分子量: 175.274
• InChiKey: QFRVVKIFIHGQCH-UHFFFAOYSA-N

物化性质

• 沸点：
  277℃
• 密度：
  0.950
• 闪点：
  123℃
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Phenylazepane
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: 2-Phenylazepane
CAS number: 3466-82-8

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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.
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: C12H17N
Molecular weight: 175.3

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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：

  2-苯基六亚甲基亚胺 在 cesium fluoride 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 92.0h， 生成 (E)-N,N-Dimethyl-6-phenyl-5-hexenylamine
  参考文献：
  名称：

  Conjugated-triene intermediates in the Sommelet-Hauser rearrangement of cyclic 1-methyl-2-phenylammonium 1-methylides.

  摘要：

  氟离子诱导的 1-甲基-1-(三甲基硅烷基)甲基-2-(2-取代苯基)吡咯烷鎓（3a）、-哌啶鎓（3b 和 3c）和-全氢氮杂卓鎓碘化物（3d 和 3e）的脱硅反应和-全氢氮杂卓碘化物（3d 和 3e），高产率地得到了含有共轭三烯键系统的八元环胺（5a）、九元环胺（5b 和 5c）和十元环胺（5d、5e、6d 和 6e）。这些三烯产物是环状 1-甲基-2-苯基铵 1-甲基化物（4）的 Sommelt-Hauser 重排的中间产物，在强碱或强酸（5b 除外）的存在下，可异构化成相应的 Sommelet-Hauser 重排产物（7）。在二甲苯中加热这些三烯，可得到斯蒂文斯重排产物（8）和开环胺（9）的混合物。在己烷中用紫外线照射三烯（5），可以选择性地生成 8。本文对反应机理进行了讨论。

  DOI：

  10.1248/cpb.39.36
• 作为产物：
  描述：

  己内酰胺 在 4-二甲氨基吡啶 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 二氯甲烷 、 乙腈 为溶剂， 反应 5.0h， 生成 2-苯基六亚甲基亚胺
  参考文献：
  名称：

  通过顺序生物催化还原和有机锂介导的重排化学酶法合成取代的氮杂

  摘要：

  Enantioenriched 2-aryl azepanes 和 2-arylbenzazepines 是通过使用亚胺还原酶的不对称还原胺化或通过使用单胺氧化酶的 deracemization 生物催化生成的。胺被转化为相应的 N'-芳基脲，在用碱处理时重排，芳基取代基通过构型稳定的苄基锂中间体立体有择地转移到杂环的 2-位。这些产品是以前无法获得的富含对映体的 2,2-二取代氮杂环庚烷和苯并氮杂。

  DOI：

  10.1021/jacs.8b11891

文献信息

• [EN] BENZOXAZEPINES AS INHIBITORS OF PI3K/m TOR AND METHODS OF THEIR USE AND MANUFACTURE<br/>[FR] BENZOXAZÉPINES COMME INHIBITEURS DE PI3K/M TOR, MÉTHODES D'UTILISATION ET DE FABRICATION BENZOXAZEPINES AS INHIBITORS OF PI3K/M TOR AND METHODS OF THEIR USE AND MANUFACTURE
  申请人：EXELIXIS INC

  公开号：WO2010138487A1

  公开（公告）日：2010-12-02

  The invention is directed to Compounds of Formula (I): the invention provides compounds that inhibit, regulate, and/or modulate P13K and/or mTOR that are useful in the treatment of hyperproliferative diseases, such as cancer, in mammals. This invention also provides methods of making the compound methods of using such compounds in the treatment of hyperproliferative diseases in mammals, especially humans, and to pharmaceutical compositions containing such compounds. For example, cancer in which activity against PI3fC-alph mTOR, or both contributes to its pathology and/or symptomatology include breast cancer mantle cell lymphoma, renal cell carcinoma, acute myelogenous leukemia, chronic myelogenous leukemia, NPM/ALK- transformed anaplastic large cell lymphoma, diffu large B cell lymphoma, rhabdomyosarcoma, ovarian cancer, endometrial cancer, cervic cancer, non small cell lung carcinoma, small cell lung carcinoma, adenocarcinoma, col cancer, rectal cancer, gastric carcinoma, hepatocellular carcinoma, melanoma, pancreat cancer, prostate carcinoma, thyroid carcinoma, anaplastic large cell lymphoma, hemangiom glioblastoma, or head and neck cancer.

  这项发明涉及式(I)的化合物：该发明提供了抑制、调节和/或调节P13K和/或mTOR的化合物，这些化合物在治疗哺乳动物的高增殖性疾病，如癌症，方面非常有用。该发明还提供了制备该化合物的方法，以及在治疗哺乳动物，特别是人类的高增殖性疾病中使用这些化合物的方法，以及含有这些化合物的药物组合物。例如，对PI3fC-α mTOR或两者都具有活性有助于其病理学和/或症状学的癌症包括乳腺癌、套细胞淋巴瘤、肾细胞癌、急性髓细胞白血病、慢性髓细胞白血病、NPM/ALK转化的间变性大细胞淋巴瘤、弥漫性大B细胞淋巴瘤、横纹肌肉瘤、卵巢癌、子宫内膜癌、宫颈癌、非小细胞肺癌、小细胞肺癌、腺癌、结肠癌、直肠癌、胃癌、肝细胞癌、黑色素瘤、胰腺癌、前列腺癌、甲状腺癌、间变性大细胞淋巴瘤、血管瘤、胶质母细胞瘤或头颈癌。
• Direct Access to Functionalized Azepanes by Cross-Coupling with α-Halo Eneformamides
  作者：Timothy K. Beng、Sidney M. Wilkerson-Hill、Richmond Sarpong

  DOI：10.1021/ol403671s

  日期：2014.2.7

  The synthesis of functionalized azepanes was accomplished through the palladium-mediated cross-coupling of α-halo eneformamides with mostly unactivated nucleophiles under mild conditions. Alkenylations proceeded with excellent stereoselectivitiy. In most cases, high yields of the coupling products were obtained.

  功能化氮杂环庚烷的合成是通过钯介导的 α-卤代烯甲酰胺与大多数未活化的亲核试剂在温和条件下交叉偶联来完成的。烯基化以优异的立体选择性进行。在大多数情况下，可以获得高产率的偶联产物。
• Direct α-C–H bond functionalization of unprotected cyclic amines
  作者：Weijie Chen、Longle Ma、Anirudra Paul、Daniel Seidel

  DOI：10.1038/nchem.2871

  日期：2018.2

  Direct α-C–H bond functionalization of unprotected cyclic amines Direct α-C–H bond functionalization of unprotected cyclic amines, Published online: 06 November 2017; doi:10.1038/nchem.2871NatureArticleSnippet(type=short-summary, markup= Cyclic amines bearing α-substituents are valuable building blocks for drug discovery and natural product synthesis. Introduction of α-substituents via site-selective

  未保护的环胺的直接α-C–H键官能化 未保护的环胺的直接α-C–H键官能化，在线发布：2017年11月6日；doi：10.1038 / nchem.2871NatureArticleSnippet（type = short-summary，markup = 带有α-取代基的环胺是药物发现和天然产物合成的重要组成部分。通过位点选择性取代C–H键引入α取代基极具吸引力，但通常仅限于受保护的胺底物。现在，基于操作上简单的氢化物转移的方法可以在未保护的胺上引入α取代基。，isJats = true）
• Antiviral agents
  申请人：SANWA KAGAKU KENKYUSHO CO., LTD.

  公开号：EP0539180A1

  公开（公告）日：1993-04-28

  Antiviral compounds (I): the symbols being as defined in the specification, are efficacious against infections caused by a variety of DNA viruses, RNA viruses and retroviruses. Other specified compounds also exhibit activity. The compounds have a wider spectrum of activity than known antiviral substances.

  抗病毒化合物（I）：在规范中定义的符号对由各种DNA病毒、RNA病毒和逆转录病毒引起的感染具有疗效。其他指定的化合物也表现出活性。这些化合物的活性谱比已知的抗病毒物质更广泛。
• Pyrroloisoquinoline antidepressants. 2. In-depth exploration of structure-activity relationships
  作者：Bruce E. Maryanoff、David F. McComsey、Joseph F. Gardocki、Richard P. Shank、Michael J. Costanzo、Samuel O. Nortey、Craig R. Schneider、Paulette E. Setler

  DOI：10.1021/jm00391a028

  日期：1987.8

  verified by enantiospecific synthesis starting with (+)-(R)-2-phenylpyrrolidine. Regarding the pendant phenyl ring, diverse substitution patterns were investigated. Those substitutions that were particularly unfavorable were 3',4',5'-trimethoxy (20b), 2',3',4',5',6'-pentafluoro (34b), 2'-trifluoromethyl (38b), 3',5'-bis(trifluoromethyl) (42b), 4'-n-butyl (44b), 2'-cyano (47b), 4'-methylsulfonyl (50b), and

  一系列吡咯并[2,1-a]异喹啉和相关化合物由于对丁苯那嗪诱导的上睑下垂和镇静作用以及对生物胺吸收的抑制作用而被检测为抗抑郁样活性。因此，我们已经鉴定出有史以来报道的一些最有效的TBZ诱导上睑下垂拮抗剂和一些最有效的多巴胺，去甲肾上腺素和血清素摄取抑制剂（在大鼠脑突触体中）。在这方面，特别值得注意的化合物分别是52b，29b，22b和48b。生物活性主要由反式异构体表现出来。而且，通过拆分四种化合物7b，24b，37b和48b，发现生物活性与（+）对映异构体亚组（在589 nm在MeOH中测得的盐）相关，对应于6S，10bR的绝对构型7b，37b，和48b，以及24b的6R，10bR配置。在（+）-24b X HBr上进行X射线测定，确定了其绝对构型；通过（+）-（R）-2-苯基吡咯烷开始的对映体特异性合成，验证了其他化合物的构型。关于侧苯环，研究了多种取代方式。那些特别不利的取代基是3'