羽扇豆宁 | 486-70-4

• 物质功能分类: 天然产物 - 生物碱
• 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: 羽扇豆宁
• 中文别名: (1R,9aR)-八氢-2H-喹嗪-1-甲醇；羽扇豆寧；羽扇豆碱；八氢-2H-喹啉嗪-1-基甲醇；(1R,9AR)-八氢-2H-喹嗪-1-甲醇
• 英文名称: lupinine
• 英文别名: Lupinin；[(1R,9aR)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl]methanol
• CAS: 486-70-4
• 化学式: C₁₀H₁₉NO
• 分子量: 169.267
• InChiKey: HDVAWXXJVMJBAR-VHSXEESVSA-N

物化性质

• 熔点：
  62-65°C
• 沸点：
  160-164°C 4mm
• 比旋光度：
  D26 -25.9° (c = 3 in water); D28 -21° (c = 9.5 in alcohol)
• 密度：
  0.9660 (rough estimate)
• 闪点：
  160-164°C/4mm
• 溶解度：
  氯仿（微溶）、乙醇（微溶、超声处理）、甲醇（微溶）
• LogP：
  1.290 (est)
• 碰撞截面：
  135.3 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

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：
  6.1
• 危险品标志：
  Xi
• 安全说明：
  S22,S36/37
• 危险类别码：
  R20/21/22
• 危险品运输编号：
  1544
• RTECS号：
  OK5802000
• 包装等级：
  III
• 危险类别：
  6.1
• WGK Germany：
  3
• 危险性防范说明：
  P233,P260,P261,P264,P270,P271,P280,P301+P312,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P330,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H332,H335

制备方法与用途

羽扇豆碱是一种羽扇豆生物碱，可用作化学农药杀虫剂的原料。

反应信息

• 作为反应物：
  描述：

  羽扇豆宁 在 三溴化磷 、 苯 作用下， 生成 bromolupinane
  参考文献：
  名称：

  603.羽扇豆碱的合成

  摘要：

  DOI：

  10.1039/jr9510002714
• 作为产物：
  描述：

  bromolupinane 在 copper(II) sulfate 作用下， 以 二甲基亚砜 为溶剂， 以81%的产率得到羽扇豆宁
  参考文献：
  名称：

  Syntheses from chiral heterocyclic β-amino esters. A new versatile access to pyrrolizidine and quinolizidine alkaloids

  摘要：

  Chiral heterocyclic P-amino esters can be easily transformed into bicyclic alkaloids after a diastereoselective alkylation followed by specific chemical transformations. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00977-7
• 作为试剂：
  描述：

  新烟碱 在 sodium amide 、 N,N-二甲基苯胺 、 羽扇豆宁 作用下， 生成 (±)-5-(piperidin-2-yl)pyridin-2-amine
  参考文献：
  名称：

  Relationship Between Physiological Loss, Performance Decrement, and Age in Master Athletes

  摘要：

  Background. The use of master athletes to describe an idealized rate of physiological loss associated with aging is quite common. The results of such studies suggest that older athletes may be able to reduce the rate of decline in functional loss. The findings of such studies have been questioned due to their limited sample size and the age range and gender of their subjects.Methods. We examined a group of 146 male and 82 female master athletes over the age of 40 years. Physiological parameters included maximal oxygen uptake ((V) over dot O(2)max), body composition, muscle strength, bone density, and blood chemistries Medical histories and training records were obtained via questionnaire.Results. Results demonstrated gender differences in body composition, blood chemistries, blood pressure, (V) over dot O(2)max, muscle strength, bone density, and performance (p < .05) All metabolic parameters for men and most for women demonstrated significant losses across the age range (p < .05). In addition, strength and performance for men and women and bone density for women declined significantly with age (p < .05). The demonstrated loss rates did not differ by gender.Conclusions. Although limited by the lack of a sedentary comparison group, these data suggest that age-related losses in (V) over dot O(2)max may not be different from data previously reported for older sedentary adults and that loss in muscle strength and performance with aging is not linear.

  DOI：

  10.1093/gerona/56.10.m618

文献信息

• Synthesis of Substituted Quinolizidines <i>via</i> a Gold-Catalyzed Double Cyclization Cascade
  作者：Shiori Nonaka、Kenji Sugimoto、Hirofumi Ueda、Hidetoshi Tokuyama

  DOI：10.1002/adsc.201500907

  日期：2016.2.4

  A novel synthesis of quinolizidines by a cationic gold‐catalyzed double cyclization cascade has been developed. The reaction was initiated by the gold‐catalyzed 6‐exo‐dig cyclization of ynamides, which was followed by a second cyclization of an enamide intermediate to provide the corresponding quinolizidine derivatives. The utility of this reaction was demonstrated by application to the synthesis of

  已开发出一种通过阳离子金催化的双环化级联反应合成喹啉嗪的新方法。该反应是由金酰胺对酰胺进行6- exo - dig环化反应引发的，然后第二次环化酰胺中间体以提供相应的喹喔啉衍生物。该反应的实用性通过应用于多取代喹oli啶类化合物的合成以及喹oli啶类生物碱（±）-羽扇豆碱的全合成而得到证明。
• Convenient One-Pot Synthesis of Chiral Tetrahydropyridines via a Multicomponent Reaction
  作者：Gérard Lhommet、Romain Noël、Marie-Claude Fargeau-Bellassoued、Corinne Vanucci-Bacqué

  DOI：10.1055/s-2008-1067092

  日期：——

  The multicomponent condensation of various β-dicarbonyl compounds, acrolein and (S)-2-phenylglycinol was found to provide a one-pot access to chiral 6-carbonyl-3-phenyl-2,3,8,8a-tetrahydro-7H-[1,3]oxazolo[3,2-a]pyridines. The value of this methodology is illustrated by the short and efficient synthesis of (-)-lupinine.

  发现多种β-二羰基化合物、丙烯醛和(S)-2-苯基甘氨酸醇的多组分缩合反应，可以一锅法合成手性6-羰基-3-苯基-2,3,8,8a-四氢-7H-[1,3]恶唑并[3,2-a]吡啶。通过(-)-羽扇豆碱的简短高效合成，展示了这种方法的价值。
• BITTER TASTE MODIFIERS INCLUDING SUBSTITUTED 1-BENZYL-3-(1-(ISOXAZOL-4-YLMETHYL)-1H-PYRAZOL-4-YL)IMIDAZOLIDINE-2,4-DIONES AND COMPOSITIONS THEREOF
  申请人：SENOMYX, INC.

  公开号：US20160376263A1

  公开（公告）日：2016-12-29

  The present invention includes compounds and compositions known to modify the perception of bitter taste, and combinations of said compositions and compounds with additional compositions, compounds, and products. Exemplary compositions comprise one or more of the following: cooling agents; inactive drug ingredients; active pharmaceutical ingredients; food additives or foodstuffs; flavorants, or flavor enhancers; food or beverage products; bitter compounds; sweeteners; bitterants; sour flavorants; salty flavorants; umami flavorants; plant or animal products; compounds known to be used in pet care products; compounds known to be used in personal care products; compounds known to be used in home products; pharmaceutical preparations; topical preparations; cannabis-derived or cannabis-related products; compounds known to be used in oral care products; beverages; scents, perfumes, or odorants; compounds known to be used in consumer products; silicone compounds; abrasives; surfactants; warming agents; smoking articles; fats, oils, or emulsions; and/or probiotic bacteria or supplements.

  本发明涵盖已知用于改变苦味感知的化合物和组合物，以及所述组合物和化合物与额外的组合物、化合物和产品的组合。示例组合物包括以下一种或多种：冷却剂；无活性药物成分；活性药用成分；食品添加剂或食品；调味剂或调味增强剂；食品或饮料产品；苦味化合物；甜味剂；苦味剂；酸味调味剂；咸味调味剂；鲜味调味剂；植物或动物产品；已知用于宠物护理产品中的化合物；已知用于个人护理产品中的化合物；已知用于家用产品中的化合物；制药制剂；局部制剂；大麻衍生或与大麻相关的产品；已知用于口腔护理产品中的化合物；饮料；香味、香水或除臭剂；已知用于消费品中的化合物；硅化合物；磨料；表面活性剂；发热剂；吸烟物品；脂肪、油脂或乳化剂；和/或益生菌或补充剂。
• [EN] PHENYL-HETEROARYL DERIVATIVES AND METHODS OF USE THEREOF<br/>[FR] DÉRIVÉS DE PHÉNYL-HÉTÉROARYLE ET PROCÉDÉS D'UTILISATION DE CEUX-CI
  申请人：TRANSTECH PHARMA INC

  公开号：WO2011103091A1

  公开（公告）日：2011-08-25

  The present invention provides phenyl-heteroaryl derivatives of Formula (I) and pharmaceutically acceptable salts thereof. These compounds are useful in the treatment of RAGE-mediated diseases such as Alzheimer's Disease. The present invention further relates to methods for the preparation of compounds of Formula (I) and pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising such compounds, and the use of such compounds and/or pharmaceutical compositions in treating RAGE-mediated diseases.

  本发明提供了式（I）的苯基-杂环芳基衍生物及其药学上可接受的盐。这些化合物在治疗RAGE介导的疾病，如阿尔茨海默病方面是有用的。本发明还涉及制备式（I）化合物及其药学上可接受的盐的方法，包括含有这些化合物的药物组合物，以及在治疗RAGE介导的疾病中使用这些化合物和/或药物组合物的用途。
• Synthesis and analgesic activity of 1-[(1,2,3-triazol-1-yl)methyl]quinolizines based on the alkaloid lupinine
  作者：Zhangeldy S. Nurmaganbetov、Viktor A. Savelyev、Yurii V. Gatilov、Oralgazy A. Nurkenov、Roza B. Seidakhmetova、Zarina T. Shulgau、Gulim K. Mukusheva、Serik D. Fazylov、Elvira E. Shults

  DOI：10.1007/s10593-021-03000-7

  日期：2021.9

  ydro-1H-quinolizines with various substituents at the C-4 position of the triazole ring. The structures of lupinine methanesulfonate and 1-[(1,2,3-triazol-1-yl)methyl]octahydroquinolizines were confirmed by X-ray structural analysis. 1-[(1,2,3-Triazol-1-yl)methyl]octahydroquinolizines containing a hydroxymethyl or 2-hydroxypropan-2-yl substituent at the C-4 position of the triazole ring exhibit pronounced

  通过引入取代的 1,2,3-三唑对生物碱羽扇豆碱的喹嗪主链进行修饰。当 NaN 3作用于羽扇豆与甲磺酰氯的反应产物时，形成羽扇豆酰叠氮化物，在 CuSO 4水溶液和抗坏血酸钠存在下与末端炔烃反应形成相应的 (1 S ,9a R )-1- [(1,2,3-triazol-1-yl)-methyl]octahydro-1 H-在三唑环的 C-4 位具有各种取代基的喹啉。羽扇豆甲磺酸盐和 1-[(1,2,3-triazol-1-yl)methyl]octahydroquinolizines 的结构通过 X 射线结构分析得到证实。在三唑环的 C-4 位含有羟甲基或 2-羟基丙-2-基取代基的 1-[(1,2,3-三唑-1-基) 甲基]八氢喹啉具有显着的镇痛活性。