(+)-新烟碱盐酸盐 | 53912-89-3

• 物质功能分类: 分析化学 - 标准品 - 标准物质
• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 中文名称: (+)-新烟碱盐酸盐
• 中文别名: (+)-假木贼碱盐酸盐
• 英文名称: anabasine hydrochloride
• 英文别名: (S)-(-)-anabasine hydrochloride；(S)-3-(piperidin-2-yl)pyridine hydrochloride；3-[(2S)-piperidin-2-yl]pyridine;hydrochloride
• CAS: 53912-89-3
• 化学式: C₁₀H₁₄N₂*ClH
• 分子量: 198.695
• InChiKey: VTMZQNZVYCJLGG-PPHPATTJSA-N

物化性质

• 熔点：
  220-222 °C
• 闪点：
  9℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  24.9
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  F,T
• 安全说明：
  S16,S36/37,S45
• 危险类别码：
  R11,R23/24/25,R39/23/24/25
• WGK Germany：
  1

制备方法与用途

生物活性

Anabasine ((S)-Anabasine) 氢氯化物是一种生物碱，存在于烟草中。作为烟碱乙酰胆碱受体（nAChRs）的全激动剂，Anabasine 能诱导表达人肌型 nAChRs 的 TE671 细胞去极化，其半数有效浓度为 0.7 µM。

靶点

nAChR

反应信息

• 作为反应物：
  描述：

  (+)-新烟碱盐酸盐 在 potassium tert-butylate 、 sodium acetate 、 copper(l) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 7.0h， 生成 (2S)-(-)-N-(5-hydroxypent-2-yn-1-yl)-2-(3-pyridyl)piperidine
  参考文献：
  名称：

  Functionalized N-propargylanabazine derivatives

  摘要：

  通过将盐酸安乃近与多聚甲醛和适当的末端炔烃进行三组份缩合，得到了侧链中含有羰基、酯基和氰基的生物碱安乃近的 N-丙炔基衍生物。异亚丙基双键的脱氰基乙基化和水合作用分别产生了 N-丙炔基安乃近的单羟基和二羟基衍生物。

  DOI：

  10.1007/s11172-009-0262-5
• 作为产物：
  描述：

  新烟碱 在 ammonium chloride 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以40%的产率得到(+)-新烟碱盐酸盐
  参考文献：
  名称：

  Spectroscopy and crystal structure of anabasine salts

  摘要：

  The anabasinium hydrochloride, hydriodide and perchlorate were characterized by IR and NMR spectroscopy as well as by X-ray diffraction. Anabasinium hydrochloride crystallizes with three independent ionic pairs in the asymmetric part of the orthorhombic unit cell, while anabasinium hydriodide and perchlorate crystals, being isostructural, are hexagonal and contain only one symmetry independent ionic pair. Despite these differences in the crystal data, both types of crystals display very similar helical solid-state patterns. The reported results combined with the CSD searches indicate an inherent tendency of anabasinium salts to crystallize with multiple asymmetric units, and to form folded arrangements in crystals. In the solid state the anabasinium cations predominantly adopt either synperiplanar or antiperiplanar conformations with respect to the mutual orientation of C*-H and pyridine C-C(N) bonds, with deformations towards, respectively, (+) synclinal or (+) anticlinal rotamers. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2006.11.037

文献信息

• Enantioselective Syntheses of 2-Alkyl-, 2,6-Dialkylpiperidines and Indolizidine Alkaloids Through Diastereoselective Mannich-Michael Reactions
  作者：Markus Weymann、Waldemar Pfrengle、Dieter Schollmeyer、Horst Kunz

  DOI：10.1055/s-1997-3185

  日期：1997.10

  Aldimines of 2,3,4,6-tetra-0-pivaloyl-β-D-galactosylamine react with 1-methoxy-3-trimethylsilyloxybuta-1,3-diene in a Mannich-Michael condensation reaction sequence to give 2-substituted N-galactosyl-5,6-dehydropiperidin-4-ones 3 with high diastereoselectivity. The X-ray analysis of the 2-propyl derivative 3a proved (R)-configuration of the major diastereomer and led to the correction of our earlier assignment of configuration for (-)-coniine hydrochloride 9a obtained from this intermediate. Despite their low reactivity, these enaminones 3 can be converted into chiral 2,6-cis-disubstituted piperidinones 12 with high stereoselectivity by reaction with organocuprates in combination with hard electrophiles. Enantiomerically pure alkaloids such as (-)-dihydropinidine and gephyrotoxine 167B have been synthesized according to this methodology.

  2,3,4,6-四-O-特戊酰基-β-D-半乳糖胺的烯胺与1-甲氧基-3-三甲基硅氧基丁-1,3-二烯在曼尼希-迈克尔缩合反应序列中反应，以高非对映选择性得到2-取代的N-半乳糖基-5,6-脱氢哌啶-4-酮3。2-丙基衍生物3a的X射线分析证实了主要非对映异构体的(R)构型，并纠正了我们之前对该中间体得到的(-)-毒芹碱盐酸盐9a的构型分配。尽管这些烯胺酮3的反应性较低，但通过与有机铜酸盐和硬亲电试剂的反应，可以高立体选择性地将其转化为手性的2,6-顺式-二取代哌啶酮12。根据这一方法，已经合成了高对映纯度的生物碱，如(-)-二氢矮牵牛素和gephyrotoxine 167B。
• Synthesis of N-aryloxyalkylanabasine derivatives
  作者：N. M. Slyn’ko、L. E. Tatarova、M. M. Shakirov、E. E. Shul’ts

  DOI：10.1007/s10600-013-0585-1

  日期：2013.5

  N-Aryloxyalkylanabasine derivatives were prepared via the reaction of anabasine hydrochloride with various aryloxyhaloalkanes in the presence of potash in DMF. The reaction occurred with retention of the chiral center C-(2) of the piperidine group. Side products of bis(aryloxy)ethanes were characterized.

  N-芳氧烷基烟碱衍生物是通过在DMF中存在氢氧化钾的条件下，将烟碱盐酸盐与各种芳氧卤烷反应而制备的。反应中保留了哌啶基团的手性中心C-(2)。双(芳氧)乙烷的副产物得到了表征。
• Diastereoselectivity of Azido-Ugi Reaction with Secondary Amines. Stereoselective Synthesis of Tetrazole Derivatives
  作者：Danil P. Zarezin、Victor N. Khrustalev、Valentine G. Nenajdenko

  DOI：10.1021/acs.joc.7b00611

  日期：2017.6.16

  diastereoselectivity of azido-Ugi reaction with cyclic amines was investigated. It was found that the reaction with α-substituted five- to seven-membered cyclic amines proceeds very efficiently to provide high control of diastereoselectivity (≤100% de) under mild conditions. Target tetrazole-derived products were isolated in excellent yields (≤98%). The reaction has a broad scope in terms of its amine, aldehyde, and

  研究了叠氮基-Ugi与环胺的非对映选择性。发现与α-取代的五元至七元环胺的反应非常有效地进行，以在温和的条件下高度控制非对映选择性（≤100％de）。分离出目标四唑衍生产品，收率极高（≤98％）。就胺，醛和异氰酸酯的性质而言，该反应具有广泛的范围。发现反应的非对映选择性取决于起始环胺的环大小。刚性更高的哌啶提供最高的反应选择性。使用苄基异氰化物，可以通过氢解将制备的N-苄基四唑脱保护以形成相应的NH四唑。
• Synthesis of N-Derivatives of Cytisine, Anabasine, and Salsoline Alkaloids with Pharmacophore 3-Aminopyridine-2(1H)-one and 5-Methyl-7-phenyloxazole[5,4-b]pyridine Cycles
  作者：I. V. Palamarchuk、D. N. Ogurtsova、T. M. Seilkhanov、I. V. Kulakov

  DOI：10.1134/s1070363219120259

  日期：2019.12

  reaction of nucleophilic substitution of 2-chloro-N-(6-methyl-2-oxo-4-phenyl-1,2-dihydropyridin-3-yl)acetamide and 2-(chloromethyl)-5-methyl-7-phenyloxazolo[5,4-b]pyridine with cytisine, anabasine, and salsoline alkaloids has afforded the corresponding derivatives. Structure of the obtained compounds has been confirmed by means of 1H and 13C NMR spectroscopy.

  2-氯-N-（6-甲基-2-氧代-4-苯基-1,2-二氢吡啶-3-基）乙酰胺与2-（氯甲基）-5-甲基-7-苯基恶唑的亲核取代反应[5,4- b ]吡啶与胞嘧啶碱，金刚烷胺和索索林生物碱已提供相应的衍生物。所获得的化合物的结构已经通过1 H和13 C NMR光谱法确认。
• Isoprenoid derivatives of N-propargylanabasine: mild hydration of a trisubstituted double bond
  作者：M. V. Mavrov、S. G. Zlotin

  DOI：10.1007/s10593-009-0330-7

  日期：2009.6

  iperidine has been synthesi-zed by the three-component condensation of (S)-anabasine with (2-cyanoethoxy)dehydrolinalool and formaldehyde. A series of previously unreported N-propargylanabasine derivatives has been synthesized from this compound.

  （2S，4' RS）-N- [4-（2-氰基乙氧基）-4,8-二甲基-壬-7-烯-2-炔-1-基] -2-（3-吡啶基）哌啶一直synthesi- （S）-天麻碱与（2-氰基乙氧基）脱氢芳樟醇和甲醛的三组分缩合反应。从该化合物合成了一系列先前未报道的N-炔丙基天麻碱衍生物。