八氢-2H-喹啉-1-甲醇 | 10159-79-2

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 羽扇豆生物碱
• 中文名称: 八氢-2H-喹啉-1-甲醇
• 英文名称: lupinine
• 英文别名: Lupinin；Epilupinin；DL-1-Epilupinin；2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-ylmethanol
• CAS: 10159-79-2
• 化学式: C₁₀H₁₉NO
• mdl: MFCD00017327
• 分子量: 169.267
• InChiKey: HDVAWXXJVMJBAR-UHFFFAOYSA-N

物化性质

• 熔点：
  68-70°C
• 沸点：
  269-270°C
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S23
• 危险类别码：
  R23/24/25
• 危险品运输编号：
  UN 1544

SDS

Name:	Octahydro-2H-quinolizin-1-ylmethanol 97% Material Safety Data Sheet
Synonym:	Lupinin
CAS:	10159-79-2

Section 1 - Chemical Product MSDS Name:Octahydro-2H-quinolizin-1-ylmethanol 97% Material Safety Data Sheet
Synonym:Lupinin

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
10159-79-2	Octahydro-2H-quinolizin-1-ylmethanol	97%	unlisted

Hazard Symbols: T
Risk Phrases: 23/24/25

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic by inhalation, in contact with skin and if swallowed.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Toxic in contact with skin.
Ingestion:
May cause irritation of the digestive tract. May cause central nervous system depression, characterized by excitement, followed by headache, dizziness, drowsiness, and nausea. Advanced stages may cause collapse, unconsciousness, coma and possible death due to respiratory failure. May cause tingling and numbness of the extremities. Continued exposure may result in muscular weakness, difficulty in maintaining balance, and clumsiness in walking and the use of hands. Toxic if swallowed.
Inhalation:
May cause respiratory tract irritation. Toxic if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid immediately. Wash mouth out with water.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 10159-79-2: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 269 - 270 deg C @755mmHg
Freezing/Melting Point: 68 - 70 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Soluble.
Specific Gravity/Density:
Molecular Formula: C10H19NO
Molecular Weight: 169

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen cyanide, nitrogen oxides, carbon monoxide, carbon dioxide, acrid smoke and fumes.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 10159-79-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Octahydro-2H-quinolizin-1-ylmethanol - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: ALKALOIDS, SOLID, N.O.S.*
Hazard Class: 6.1
UN Number: 1544
Packing Group: III
IMO
Shipping Name: ALKALOID SALTS, SOLID, N.O.S.
Hazard Class: 6.1
UN Number: 1544
Packing Group: III
RID/ADR
Shipping Name: ALKALOIDS, SOLID, N.O.S.
Hazard Class: 6.1
UN Number: 1544
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T
Risk Phrases:
R 23/24/25 Toxic by inhalation, in contact with skin
and if swallowed.
Safety Phrases:
S 28A After contact with skin, wash immediately with
plenty of water.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 38 In case of insufficient ventilation, wear
suitable respiratory equipment.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 10159-79-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 10159-79-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 10159-79-2 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  八氢-2H-喹啉-1-甲醇 在 三苯基乙酸 、 盐酸 作用下， 以 氯仿 、 水 为溶剂， 以53%的产率得到1-表羽扇豆碱
  参考文献：
  名称：

  简明的不对称全合成（+）-艾比林宁

  摘要：

  仅使用市售通用试剂，仅需三个步骤即可实现（+）-艾比卢皮碱的不对称全合成。总的合成涉及N-烷基酰胺的烷基化，臭氧氧化，以及去除烷基的顺序反应，分子内脱水缩合，1-脯氨酸催化的分子内曼尼希反应和还原。

  DOI：

  10.1021/acs.orglett.9b00607
• 作为产物：
  描述：

  1-(6-Hydroxyhex-4-ynyl)-2-(trimethylsilyl)piperidine 在 Lindlar's catalyst 四氯化碳 、 sodium tetrahydroborate 、 二甲基硫 、 萘-1,4-二腈 、 氢气 、 potassium carbonate 、 臭氧 、 三苯基膦 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 异丙醇 为溶剂， -78.0~25.0 ℃ 、241.32 kPa 条件下， 反应 16.0h， 生成 八氢-2H-喹啉-1-甲醇
  参考文献：
  名称：

  Stereoselectivity in the photoinduced electron transfer (PET) promoted intramolecular cyclisations of 1-alkenyl-2-silyl-piperidines and -pyrrolidines: rapid construction of 1-azabicyclo[m.n.0]alkanes and stereoselective synthesis of (±)-isoretronecanol and (±)-epilupinine

  摘要：

  PET promoted cyclisations of 1-alkenyl-2-silyl-pyrrolidines and -piperidines 9a-d to 1-aza-bicyclo[m.n.0]alkanes have been found to be stereoselective. The five-membered ring formation gives predominantly cis products while six-membered rings are trans. Application of such cyclisations to the synthesis of (+/-)-isoretronecanol 22a, (+/-)-epilupinine 29 and related alkaloids has been demonstrated.

  DOI：

  10.1039/p19960000219

文献信息

• Organocatalytic Asymmetric Mannich Cyclization of Hydroxylactams with Acetals: Total Syntheses of (−)-Epilupinine, (−)-Tashiromine, and (−)-Trachelanthamidine
  作者：Dipankar Koley、Yarkali Krishna、Kyatham Srinivas、Afsar Ali Khan、Ruchir Kant

  DOI：10.1002/anie.201407185

  日期：2014.11.24

  cyclization between a hydroxylactam and acetal is described to provide fused, bicyclic alkaloids bearing a bridgehead N atom. Both aliphatic and aromatic substrates were used in this transformation to furnish chiral pyrrolizidinone, indolizidinone, and quinolizidinone derivatives in up to 89 % yield and 97 % ee. The total syntheses of (−)‐epilupinine, (−)‐tashiromine, and (−)‐trachelanthamidine also

  羟基内酰胺和乙缩醛之间的不对称有机催化单锅曼尼希环化反应可提供带有桥头N原子的稠合双环生物碱。脂肪族和芳香族底物均用于该转化中，以高达89％的收率和97％的ee值提供手性吡咯烷酮，吲哚啶酮和喹喔啉酮衍生物。（-）-癫痫素，（-）-tashiromine和（-）-trachelanthamidine的总合成也证明了该方法的普遍性。
• ARYL-SUBSTITUTED POLYCYCLIC AMINES, METHOD FOR THE PRODUCTION THEREOF, AND USE THEREOF AS A MEDICAMENT
  申请人：SCHWINK Lothar

  公开号：US20070197584A1

  公开（公告）日：2007-08-23

  The invention relates to aryl-substituted polycyclic amines of the formula I, especially bicyclic amines, and to the physiologically tolerated salts and physiologically functional derivatives thereof; where the symbols and radicals are explained in the description as well as to pharmaceutical compositions and medical treatments employing these compounds.

  该发明涉及公式I的芳基取代的多环胺，特别是双环胺，以及其生理耐受的盐和生理功能衍生物；其中符号和基团在描述中有解释，还涉及使用这些化合物的药物组合物和医疗治疗。
• Synthesis and comparison of antiplasmodial activity of (+), (−) and racemic 7-chloro-4-(N-lupinyl)aminoquinoline
  作者：Chiara Rusconi、Nadia Vaiana、Manolo Casagrande、Nicoletta Basilico、Silvia Parapini、Donatella Taramelli、Sergio Romeo、Anna Sparatore

  DOI：10.1016/j.bmc.2012.07.041

  日期：2012.10

  issue, the corresponding racemic compound, derived from synthetic (±)-lupinine was considered a cheaper alternative for the development of a novel antimalarial agent. Therefore, the racemic and the 7-chloro-4-(N-(+)-lupinyl)aminoquinoline ((±)-AM-1; (+)-AM-1) were synthesized and their in vitro antimalarial activity and cytotoxicity compared with those of (−)-AM-1. The (+)-lupinine required for the synthesis

  最近Ñ - （ - ） - lupinyl衍生物7-氯-4-氨基喹啉的（（ - ） - AM-1; 7-氯-4- ñ - [（1-小号，9A ř）（八氢-2 ħ -喹啉嗪-1-基）甲基]氨基}喹啉对恶性疟原虫的氯喹敏感和耐药菌株均显示出有效的体外和体内活性。然而，（-）-AM-1是从（-）-羽扇豆碱（一种从羽扇豆羽扇豆中分离出来的昂贵生物碱）开始合成的目前，其全球产量不足以满足大型市场的需求。为了克服这个问题，衍生自合成（±）-羽扇豆碱的相应外消旋化合物被认为是开发新型抗疟药的廉价替代品。因此，合成了外消旋和7-氯-4-（N -（+）-羽扇豆基）氨基喹啉（（±）-AM-1;（+）-AM-1），并比较了它们的体外抗疟活性和细胞毒性。 （-）-AM-1的那些。合成（+）-AM-1所需的（+）-羽扇豆碱是通过先前未描述的脂肪酶催化的（±）-羽扇豆碱的动力学拆分而获得的。就抗疟疾活性而言，（±
• Quinolizidine alkaloids and the enzymatic syntheses of their cinnamic and hydroxycinnamic acid esters in Lupinus angustifolius and L. Luteus
  作者：Dieter Strack、Andrea Becher、Sabine Brall、Ludger Witte

  DOI：10.1016/0031-9422(91)84195-x

  日期：1991.1

  and L. luteus are described. The enzymes catalysing the syntheses of the cinnamic acid O -ester of 13-hydroxylupanine and hydroxycinnamic acid O -esters of lupinine (4-coumaroyl- and feruloyllupinine) are characterized and classified as cinnamoyl-CoA: 13-hydroxylupanine O -cinnamoyltransferase (EC 2.3. 1.-) and hydroxycinnamoyl-CoA: lupinine O -hydroxycinnamoyltransferase (EC 2.3. 1.-).

  摘要 描述了羽扇豆(Lupinus angustifolius) 和黄花羽扇豆(L. luteus) 幼苗和幼苗发育过程中喹尼西啶生物碱的积累规律。催化 13-羟基羽扇豆氨酸的肉桂酸 O-酯和羽扇豆碱的羟基肉桂酸 O-酯（4-香豆酰-和阿魏酰羽扇豆碱）合成的酶被表征并归类为肉桂酰辅酶 A：13-羟基羽扇豆氨酸 O-肉桂酰转移酶（EC .1.-)和羟基肉桂酰-CoA：羽扇豆碱O-羟基肉桂酰转移酶(EC 2.3. 1.-)。
• USE OF ARYL-SUBSTITUTED POLYCYCLIC AMINES AS MEDICAMENTS
  申请人：SCHWINK Lothar

  公开号：US20090258872A1

  公开（公告）日：2009-10-15

  The invention relates to therapeutic use of aryl-substituted polycyclic amines of the formula I, especially bicyclic amines, and to the physiologically tolerated salts and physiologically functional derivatives thereof; where the symbols and radicals are explained in the description.

  本发明涉及公式I的芳基取代多环胺的治疗用途，特别是双环胺，以及其生理上耐受的盐和生理上功能性衍生物；其中符号和基团在说明中解释。