外向-8-苄基-8-氮杂双环[3.2.1]辛-3-胺 | 76272-36-1

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 外向-8-苄基-8-氮杂双环[3.2.1]辛-3-胺
• 中文别名: 3-氨基-8-苄基-8-8-氮杂双环[3,2,1]辛烷；N-苄基-托品胺
• 英文名称: 8-benzyl-8-azabicyclo[3.2.1]octan-3-amine
• 英文别名: (1R,5S)-8-benzyl-8-azabicyclo[3.2.1]octan-3-amine；8-Benzyl-3a-amino-1aH,5aH-nortropane；(1S,5R)-8-benzyl-8-azabicyclo[3.2.1]octan-3-amine
• CAS: 76272-36-1；76272-35-0
• 化学式: C₁₄H₂₀N₂
• 分子量: 216.326
• InChiKey: TZWXPIKAEAYGPF-AGUYFDCRSA-N

物化性质

• 沸点：
  110-115 °C(Press: 0.05 Torr)
• 密度：
  1.082±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

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: 8-Benzyl-8-azabicyclo[3.2.1]octan-3-exo-amine
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: 8-Benzyl-8-azabicyclo[3.2.1]octan-3-exo-amine
CAS number: 76272-36-1

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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: C14H20N2
Molecular weight: 216.3

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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

制备方法与用途

概述

外向-8-苄基-8-氮杂双环[3.2.1]辛-3-胺是一种杂环化合物，可用作医药合成中间体。

应急措施

若吸入外向-8-苄基-8-氮杂双环[3.2.1]辛-3-胺，请将患者移至新鲜空气处；若皮肤接触，应脱去污染衣物，并用肥皂水和清水彻底清洗；如有不适，请就医。若眼睛接触到该物质，请分开眼睑，用流动清水或生理盐水冲洗，并立即就医。若误食，请立即漱口，禁止催吐，并立即就医。

反应信息

• 作为反应物：
  描述：

  外向-8-苄基-8-氮杂双环[3.2.1]辛-3-胺 在 吡啶 、 盐酸 、 五氯化磷 、 palladium 10% on activated carbon 、 氢气 、 三乙酰氧基硼氢化钠 、 sodium carbonate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 32.5h， 生成 马拉维若
  参考文献：
  名称：

  基于废物再利用策略的不对称曼尼希反应和一锅含α-酰胺基砜的含轴向手性砜的苯乙烯的构建

  摘要：

  证明了同时不对称曼尼希反应和基于废物-再利用策略的一锅中由α-酰胺基砜构建的轴向手性含砜基苯乙烯的结构。在温和条件下，以良好至极佳的收率和对映选择性，合成了一系列具有各种官能团的手性β-氨基二酯和轴向手性含砜基的苯乙烯。此外，该方案已成功应用于合成抗HIV药物Maraviroc和手性三氯衍生物。

  DOI：

  10.1021/acs.orglett.8b02087
• 作为产物：
  描述：

  tert-butyl (8-benzyl-8-azabicyclo[3.2.1]octan-3-yl)carbamate 在 盐酸 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 1.0h， 生成 外向-8-苄基-8-氮杂双环[3.2.1]辛-3-胺
  参考文献：
  名称：

  的发现和生物学评价ñ -甲基吡咯并[2,3- b ]吡啶-5-甲酰胺衍生物作为JAK1选择性抑制剂

  摘要：

  Janus激酶1（JAK1）在大多数细胞因子介导的通过JAK / STAT信号传导的炎症和自身免疫反应中起关键作用；因此，抑制JAK1是对几种疾病的有前途的治疗策略。分析目前的JAK抑制剂与JAK同工型的结合方式，可以设计N-烷基取代的1- H-吡咯并[2,3- b ]吡啶羧酰胺作为JAK1选择性骨架，并合成各种甲基酰胺衍生物提供了4-（（顺式-1-（4-氯苄基）-2-甲基哌啶-4-基）氨基）-N-甲基-1H-吡咯并[2,3 - b ]吡啶-5-甲酰胺（31g），一种有效的JAK1选择性抑制剂。特别是（31 g（38a）的S，S） -对映异构体对JAK1表现出出色的效力，并具有超过JAK2，JAK3和TYK2的选择性。在研究31g对肝纤维化的作用时，发现它降低了TGF-β诱导的肝星状细胞（HSCs）的增殖和纤维生成基因表达。具体而言，在伤口愈合试验中，31g显着抑制TGF-β诱导的0.25μMHSC迁移。

  DOI：

  10.1021/acs.jmedchem.0c01026

文献信息

• [EN] NOVEL CARBOXAMIDE DERIVATIVES AS HIV INHIBITORS<br/>[FR] NOUVEAUX DÉRIVÉS CARBOXAMIDES COMME INHIBITEURS DU VIH
  申请人：HETERO RESEARCH FOUNDATION

  公开号：WO2011061590A1

  公开（公告）日：2011-05-26

  The present invention relates to carboxamide derivatives of Formula (I), where B1, B2, X, L, n, R, R1, R2, Z1, Z2, Rx and Ry are as defined in the claims, as compounds and compositions for inhibiting Human Immunodeficiency Virus (HIV) and process for making the compounds.

  本发明涉及公式（I）的羧酰胺衍生物，其中B1、B2、X、L、n、R、R1、R2、Z1、Z2、Rx和Ry如权利要求中所定义的那样，作为抑制人类免疫缺陷病毒（HIV）的化合物和组合物，以及制备这些化合物的方法。
• Asymmetric Synthesis of Maraviroc (UK-427,857)
  作者：Gui-Ling Zhao、Shuangzheng Lin、Aleš Korotvička、Luca Deiana、Martin Kullberg、Armando Córdova

  DOI：10.1002/adsc.201000287

  日期：2010.9.10

  The asymmetric synthesis of Maraviroc (UK‐427,857), a chemochine receptor 5 (CCR‐5) receptor antagonist, based on an expeditious organocatalytic enantioselective assembly of the chiral β‐amino aldehyde key fragment is presented. The reactions were performed on a gram‐scale and allow for the rapid construction of new Maraviroc analogues.

  基于手性β-氨基醛键片段的快速有机催化对映选择性组装，提出了趋化因子受体5（CCR-5）受体Maraviroc（UK-427,857）的不对称合成。反应以克为单位进行，可以快速构建新的Maraviroc类似物。
• HETEROARYL-SUBSTITUTED SULFONAMIDE COMPOUNDS AND THEIR USE AS SODIUM CHANNEL INHIBITORS
  申请人：Xenon Pharmaceuticals Inc.

  公开号：US20200071313A1

  公开（公告）日：2020-03-05

  This invention is directed to heteroaryl-substituted sulfonamide compounds, as stereoisomers, enantiomers, tautomers thereof or mixtures thereof; or pharmaceutically acceptable salts, solvates or prodrugs thereof, for the treatment of diseases or conditions associated with voltage-gated sodium channels, such as epilepsy.

  这项发明涉及杂环取代磺酰胺化合物，包括其立体异构体、对映异构体、互变异构体或其混合物；或其药用可接受盐、溶剂合物或前药，用于治疗与电压门控钠通道相关的疾病或症状，如癫痫。
• Heteroaryl-substituted sulfonamide compounds and their use as sodium channel inhibitors
  申请人：Xenon Pharmaceuticals Inc.

  公开号：US10752623B2

  公开（公告）日：2020-08-25

  This invention is directed to heteroaryl-substituted sulfonamide compounds, as stereoisomers, enantiomers, tautomers thereof or mixtures thereof; or pharmaceutically acceptable salts, solvates or prodrugs thereof, for the treatment of diseases or conditions associated with voltage-gated sodium channels, such as epilepsy.

  本发明涉及杂芳基取代的磺酰胺化合物，作为其立体异构体、对映体、同系物或其混合物；或其药学上可接受的盐、溶液剂或原药，用于治疗与电压门控钠通道相关的疾病或病症，如癫痫。
• EP1403255
  申请人：——

  公开号：——

  公开（公告）日：——