八氢-1H-异吲哚 | 21850-12-4

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: 八氢-1H-异吲哚
• 中文别名: 顺式全氢异吲哚；顺式-全氢异吲哚；顺式全氢异吲哚盐酸盐
• 英文名称: octahydro-1H-isoindole
• 英文别名: perhydroisoindole；cycloperhydroisoindole；2,3,3a,4,5,6,7,7a-octahydro-1H-isoindole
• CAS: 21850-12-4
• 化学式: C₈H₁₅N
• mdl: MFCD03265253
• 分子量: 125.214
• InChiKey: ODSNARDHJFFSRH-UHFFFAOYSA-N

物化性质

• 沸点：
  90 °C(Press: 14 Torr)
• 密度：
  1.081 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2～8℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Octahydro-isoindole
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: Octahydro-isoindole
CAS number: 21850-12-4

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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: C8H15N
Molecular weight: 125.2

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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.

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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

合成方法主要有三种：

1. 以顺式四氢邻苯二甲酰亚胺为原料，通过四氢锂铝还原得顺式异二氢吲哚，再经催化氢化得到顺式全氢异吲哚。
2. 以邻苯二腈为原料，经钯碳催化氢化还原后得异二氢吲哚，再使用钌催化剂进行催化氢化反应，最终得到顺式全氢异吲哚。
3. 以顺式六氢邻苯二甲酰胺为原料，利用四氢锂铝、硼烷-四氢呋喃络合物、硼氢化钠-硫酸复合体系或硼氢化钾-氯化镁复合体系还原，从而得到顺式全氢异吲哚。

前两种方法均需使用价格较高的过渡金属催化剂，成本较高，难以应用于大规模生产。第三种方法使用的原料较为廉价易得，但四氢锂铝和硼烷-四氢呋喃络合物均具有易燃易爆的特性，且价格高昂，反应条件苛刻，同样不适合工业生产。即使使用硼氢化钠-硫酸复合体系或硼氢化钾-氯化镁复合体系，收率较低，还需采用沸点较低的四氢呋喃溶剂才能获得最佳结果。因此，这种方法在实际应用中存在收率不高、溶剂易燃易爆、回收困难以及试剂用量大导致生产成本较高的问题。

反应信息

• 作为反应物：
  描述：

  八氢-1H-异吲哚 在 potassium nitrite 、 tetrabutylammonium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以60%的产率得到2-nitrosooctahydro-1H-isoindole
  参考文献：
  名称：

  亚硝酸钾/亚硝酸钠作为亚硝化剂在仲胺的电氧化 N-亚硝化中的应用

  摘要：

  已经开发了一种使用亚硝酸钾/亚硝酸钠作为亚硝化剂的仲胺的有效和环境电氧化N-亚硝化。这种策略突破了亚硝酸钠和强酸的先天组合。该反应与药物化合物的后期修饰相容，可以以克级规模进行，反应效率高。

  DOI：

  10.1002/ejoc.202100363
• 作为产物：
  描述：

  六氢邻苯二甲酰亚胺 在 lithium aluminium tetrahydride 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 八氢-1H-异吲哚
  参考文献：
  名称：

  New tertiary 8-hydroxyquinoline-7-carboxamide derivatives and uses thereof

  摘要：

  新的三级8-羟基喹啉-7-甲酰胺衍生物的一般化学式（I）及其药用盐已被披露。 这些化合物可用作抗真菌剂。具体来说，这些化合物已对白色念珠菌、白色念珠菌、黑曲霉和短柄曲霉进行了测试。这些化合物也对白色念珠菌属的物种如白色念珠菌和光滑白色念珠菌具有活性。

  公开号：

  EP2345643A1
• 作为试剂：
  描述：

  八氢-1H-异吲哚 、 S-2-苄基琥珀酸 在 八氢-1H-异吲哚 作用下， 生成 米格列奈
  参考文献：
  名称：

  Succinic acid compounds

  摘要：

  分子式为：##STR1## 的琥珀酸化合物，其中A代表杂环基团、3至8个成员的环烷基团或苯基团，可以具有来自卤素原子、具有1至6个碳原子的低烷基团和具有1至6个碳原子的低烷氧基团的一个或多个取代基；B代表一个具有1或2个不饱和键的双环氨基团，但B与氮原子上的羰基团的碳原子连接，R代表氢原子或结合在一起形成化学键；R.sup.1代表氢原子、具有1至6个碳原子的低烷基团或具有7至10个碳原子的芳基烷基团；当存在不对称碳原子时，其对映异构体和外消旋混合物；当存在几何异构体时，每个几何异构体、E-异构体、Z-异构体、顺式异构体和反式异构体；以及其药学上可接受的盐，能增强胰岛素分泌并具有降血糖作用，因此对于糖尿病的治疗是有用的。

  公开号：

  US05202335A1

文献信息

• [EN] INDAZOLE- AND PYRROLOPYRIDINE-DERIVATIVE AND PHARMACEUTICAL USE THEREOF<br/>[FR] DÉRIVÉ D'INDAZOLE ET PYRROLOPYRIDINE ET UTILISATION PHARMACEUTIQUE DE CELUI-CI
  申请人：DAINIPPON SUMITOMO PHARMA CO

  公开号：WO2012169649A1

  公开（公告）日：2012-12-13

  The present invention relates to a novel indazole- or pyrrolopyridine-derivative, represented by the formula (1) below, that has an agonistic action or a partial agonistic action against serotonin-4 receptor, and a pharmaceutical composition comprising the same. Formula (1) [wherein each substituent is as defined in claim 1]

  本发明涉及一种新型吲唑基或吡咯吡啶基衍生物，由下面的式（1）表示，该衍生物对5-羟色胺-4受体具有激动作用或部分激动作用，并且包括含有该衍生物的药物组合物。式（1）[其中每个取代基如权利要求1所定义]
• THERAPEUTIC AGENT FOR CEREBRAL INFARCTION
  申请人：Nakao Akira

  公开号：US20120196824A1

  公开（公告）日：2012-08-02

  The invention provides a therapeutic drug for ischemic stroke. The therapeutic drug has the formula (I) wherein each symbol is as defined herein, or a pharmacologically acceptable salt thereof, or a solvate thereof, as an active ingredient.

  这项发明提供了一种用于缺血性中风的治疗药物。该治疗药物具有如下式（I）的化学式，其中每个符号如本文所定义，或其药理学上可接受的盐，或其溶剂化物，作为活性成分。
• Piperidine derivative and use thereof
  申请人：Ikeura Yoshinori

  公开号：US20060142337A1

  公开（公告）日：2006-06-29

  The present invention provides a compound represented by the formula: wherein Ar is an aryl group optionally having substituents, R is a C 1-6 alkyl group, R 1 is a hydrogen atom, a hydrocarbon group optionally having substituents, an acyl group or a heterocyclic group optionally having substituents, X is an oxygen atom or an imino group optionally having substituents, ring A is a piperidine ring optionally further having substituents, and ring B is a benzene ring having substituents, or a salt thereof, and an agent for the prophylaxis or treatment of lower urinary tract abnormality and the like, which contains the compound.

  本发明提供了一种由以下公式表示的化合物： 其中Ar是一个芳基基团，可选地具有取代基，R是一个C1-6烷基基团，R1是一个氢原子，一个可选地具有取代基的烃基团，酰基团或杂环基团，X是一个氧原子或一个可选地具有取代基的亚胺基团，环A是一个哌啶环，可选地进一步具有取代基，环B是一个苯环，具有取代基，或其盐，以及含有该化合物的预防或治疗下尿道异常等的药剂。
• Hydroisoindoline tachykinin receptor antagonists
  申请人：Bunda Lynn Jaime

  公开号：US20050165083A1

  公开（公告）日：2005-07-28

  The present invention is directed to certain hydroisoindoline compounds which are useful as neurokinin-1 (NK-1) receptor antagonists, and inhibitors of tachykinin and in particular substance P. The invention is also concerned with pharmaceutical formulations comprising these compounds as active ingredients and the use of the compounds and their formulations in the treatment of certain disorders, including emesis, urinary incontinence, depression, and anxiety.

  本发明涉及某些羟基异吲哚啉化合物，其作为神经激肽-1（NK-1）受体拮抗剂以及缓激肽和特别是P物质的抑制剂而有用。该发明还涉及包含这些化合物作为活性成分的药物配方，以及这些化合物及其配方在治疗某些疾病，包括呕吐、尿失禁、抑郁症和焦虑症中的用途。
• [EN] OCTAHYDROCYCLOPENTAPYRROLES, THEIR PREPARATION AND USE<br/>[FR] OCTAHYDROCYCLOPENTAPYRROLES, LEUR PRÉPARATION ET LEUR UTILISATION
  申请人：UNIV COLUMBIA

  公开号：WO2014152018A1

  公开（公告）日：2014-09-25

  The present invention provides Octahydrocyclopentapyrrole compounds having the structure: (structurally represented) wherein psi is absent or present, and when present is a bond; R1, R2, R3, R4, and R5 are each independently H, halogen, CF, or C1-C4 alkyl; R6 is absent or present, and when present is H, OH, or halogen; A is absent or present, and when present is C(O) or C(O)NH; B is substituted or unsubstituted monocycle, bicycle, heteromonocycle, heterobicycle, benzyl, CO2H or (C1-C4 alkyl)-CO2H, wherein when B is CO2H, then A is present and is C(O); and when psi is present, then R6 is absent and when psi is absent, then R6 is present, or a pharmaceutically acceptable salt thereof, for treatement of diseases characterized by excessive lipofuscin accumulation in the retina.

  本发明提供了具有以下结构的八氢环戊吡咯化合物：(结构表示) 其中psi为不存在或存在，当存在时为键；R1、R2、R3、R4和R5各自独立为H、卤素、CF或C1-C4烷基；R6不存在或存在，当存在时为H、OH或卤素；A不存在或存在，当存在时为C(O)或C(O)NH；B为取代或未取代的单环、双环、杂单环、杂双环、苄基、CO2H或(C1-C4烷基)-CO2H，其中当B为CO2H时，A存在且为C(O)；且当psi存在时，R6不存在，当psi不存在时，R6存在，或其药用可接受盐，用于治疗以视网膜过度脂褐素积聚为特征的疾病。