3-azabicyclo[3.3.0]octane hydrochloride | 112626-50-3

• 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 - 吡咯烷类
• 英文名称: 3-azabicyclo[3.3.0]octane hydrochloride
• 英文别名: cis-octahydrocyclopenta[c]pyrrole hydrochloride；(3aR,6aS)-octahydrocyclopenta[c]pyrrole hydrochloride；(3aS,6aR)-1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrole;hydrochloride
• CAS: 112626-50-3
• 化学式: C₇H₁₃N*ClH
• 分子量: 147.648
• InChiKey: HVZRRRPCVOJOLJ-UKMDXRBESA-N

物化性质

• 熔点：
  131 - 135°C
• 溶解度：
  氯仿（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Azabicyclo[3.3.0]octane, HCl
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: 3-Azabicyclo[3.3.0]octane, HCl
CAS number: 112626-50-3

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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: C7H13N.ClH
Molecular weight: 147.6

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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 chloride.

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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：

  3-azabicyclo[3.3.0]octane hydrochloride 在 sodium chloride dihydrate 作用下， 以 甲基叔丁基醚 为溶剂， 反应 2.0h， 生成 (3aR,6aS)-1,3a,4,5,6,6a-hexahydrocyclopenta[c]pyrrole
  参考文献：
  名称：

  一种特拉匹韦中间体的制备方法

  摘要：

  一种特拉匹韦中间体的制备方法，包括以下步骤：（1）（3aR,6aS）-1,3a,4,5,6,6a-六氢环戊烷并吡咯的合成；（2）（3aR,6aS）-八氢环戊烷并吡咯-1-硫酸钠的合成；（3）（3aR,6aS）-八氢环戊烷并吡咯-1-氰的合成；（4）（3aR,6aS）-八氢环戊烷并吡咯-1-羧酸的合成；（5）（3aR,6aS）-2-Boc八氢环戊烷并吡咯-1-羧酸的合成；（6）（1s，3aR,6aS）-2-Boc八氢环戊烷并吡咯-1-羧酸的合成；（7）（1s,3aR,6aS）-2-Boc八氢环戊烷并吡咯-1-羧酸乙酯盐的合成。本发明工艺合理，试剂便宜易得，成本低廉；操作简便，反应容易控制。

  公开号：

  CN103664739B
• 作为产物：
  描述：

  octahydrocyclopenta[c]pyrrole 、 盐酸 在 甲基叔丁基醚 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以The product is isolated by filtration in the form of a solid in a yield of 83% and with a chemical purity of 99%的产率得到3-azabicyclo[3.3.0]octane hydrochloride
  参考文献：
  名称：

  SYNTHESIS PROCESS, AND CRYSTALLINE FORM OF 4- BENZAMIDE HYDROCHLORIDE AND PHARMACEUTICAL COMPOSITIONS CONTAINING IT

  摘要：

  公式（I）的工业合成过程：

  公开号：

  US20140100374A1

文献信息

• Ni-Catalyzed Carbon–Carbon Bond-Forming Reductive Amination
  作者：Christoph Heinz、J. Patrick Lutz、Eric M. Simmons、Michael M. Miller、William R. Ewing、Abigail G. Doyle

  DOI：10.1021/jacs.7b12212

  日期：2018.2.14

  describes a three-component, Ni-catalyzed reductive coupling that enables the convergent synthesis of tertiary benzhydryl amines, which are challenging to access by traditional reductive amination methodologies. The reaction makes use of iminium ions generated in situ from the condensation of secondary N-trimethylsilyl amines with benzaldehydes, and these species undergo reaction with several distinct classes

  本报告描述了一种三组分、Ni 催化的还原偶联，它能够聚合合成二苯甲基叔胺，这是传统还原胺化方法难以获得的。该反应利用仲 N-三甲基甲硅烷基胺与苯甲醛缩合原位生成的亚胺离子，这些物质与几种不同类别的有机亲电试剂发生反应。抗偏头痛药物氟桂利嗪 (Sibelium) 的一步合成以及帕罗西汀 (Paxil) 和美托洛尔 (Lopressor) 的高产衍生化证明了该工艺的合成价值。机理研究支持顺序氧化加成机制，而不是通过 α-氨基自由基形成进行的途径。因此，
• Structure activity refinement of phenylsulfonyl piperazines as antimalarials that block erythrocytic invasion
  作者：William Nguyen、Madeline G. Dans、Anna Ngo、Maria R. Gancheva、Ornella Romeo、Sandra Duffy、Tania F. de Koning-Ward、Kym N. Lowes、Helene Jousset Sabroux、Vicky M. Avery、Danny W. Wilson、Paul R. Gilson、Brad E. Sleebs

  DOI：10.1016/j.ejmech.2021.113253

  日期：2021.3

  asexual stage activity and determined the alpha-carbonyl S-methyl isomer was important for antimalarial potency. The optimized compounds also possessed comparable activity against multidrug resistant strains of P. falciparum and displayed weak activity against sexual stage gametocytes. We determined that the optimized compounds blocked erythrocyte invasion consistent with the asexual activity observed and

  对由青蒿素衍生物组成的联合疗法的新出现的耐药性促使人们需要鉴定具有新作用机制的新抗疟药。疟原虫的裂殖子对红细胞的入侵是疟原虫存活和增殖的关键，它为新型疗法提供了有吸引力的靶标。使用表达纳米荧光素酶生物发光报告基因的转基因恶性疟原虫寄生虫对疟疾风险病原体药进行的筛选确定了苯磺酰哌嗪类是红细胞入侵的特异性抑制剂。在这里，我们描述了苯磺酰基哌嗪类的优化和进一步表征。在优化过程中，我们定义了所需的功能恶性疟原虫的无性阶段活性和确定的α-羰基S-甲基异构体对抗疟药效力很重要。优化的化合物还对恶性疟原虫的多药耐药菌株具有可比的活性，并且对性阶段配子细胞显示出弱的活性。我们确定优化的化合物可以阻止与观察到的无性活动相一致的红细胞入侵，因此所描述的苯磺酰基哌嗪类似物可以作为研究疟原虫红细胞入侵的有用工具。
• [EN] COMPOUNDS AND COMPOSITIONS AS MODULATORS OF TLR SIGNALING<br/>[FR] COMPOSÉS ET COMPOSITIONS UTILISÉS EN TANT QUE MODULATEURS DE LA SIGNALISATION TLR
  申请人：NEUROPORE THERAPIES INC

  公开号：WO2020198368A1

  公开（公告）日：2020-10-01

  The present disclosure relates to compounds, pharmaceutical compositions comprising such compounds, and use of such compounds in methods of treatment or in medicaments for treatment of inflammatory diseases and certain neurological disorders that are related to inflammatory signaling processes, including but not limited to misfolded proteins.

  本发明公开涉及化合物、包含此类化合物的药物组合物，以及此类化合物在治疗炎症性疾病和与炎症信号传导过程相关的某些神经障碍的方法或药物中的用途，所述神经障碍包括但不限于错误折叠的蛋白质。
• Chimeric self-sufficient P450cam-RhFRed biocatalysts with broad substrate scope
  作者：Aélig Robin、Valentin Köhler、Alison Jones、Afruja Ali、Paul P Kelly、Elaine O'Reilly、Nicholas J Turner、Sabine L Flitsch

  DOI：10.3762/bjoc.7.173

  日期：——

  A high-throughput screening protocol for evaluating chimeric, self-sufficient P450 biocatalysts and their mutants against a panel of substrates was developed, leading to the identification of a number of novel biooxidation activities.

  开发了一种高通量筛选方案，用于评估嵌合的、自给自足的 P450 生物催化剂及其针对一组底物的突变体，从而确定了许多新的生物氧化活性。
• Solvent-Free Synthesis of Cyanoformamides from Carbamoyl Imidazoles
  作者：Jeremy Nugent、Sarah G. Campbell、Yen Vo、Brett D. Schwartz

  DOI：10.1002/ejoc.201700974

  日期：2017.9.15

  Secondary and tertiary cyanoformamides have been synthesized with a solvent-free approach from carbamoyl imidazoles and TMSCN. This method negates the need to use large excesses of toxic reagents and is amenable to large-scale synthesis.

  仲和叔氰基甲酰胺已由无溶剂方法由氨基甲酰基咪唑和TMSCN合成。该方法不需要使用大量过量的有毒试剂，并且适合大规模合成。