allomuscarine | 2209-03-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allomuscarine
• 英文别名: (+/-)-allo-muscarine iodide；allo-Muscariniodid；d,l-Allomuscarin-iodid；(+/-)-Allomuscarin; Jodid；[(2S,4S,5R)-4-hydroxy-5-methyloxolan-2-yl]methyl-trimethylazanium;iodide
• CAS: 2209-03-2
• 化学式: C₉H₂₀NO₂*I
• 分子量: 301.168
• InChiKey: PMFYONXEPDMBPE-KEMIKLHMSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.77
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-deoxy-3,5-di-O-p-toluoyl-α-D-erythropentofuranosyl 1-cyanide 在 吡啶 、 盐酸 、 甲醇 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 73.0h， 生成 allomuscarine
  参考文献：
  名称：

  Stereospecific synthesis of muscarines and allomuscarines in D- and L-series

  摘要：

  DOI：

  10.1021/jo00341a003

文献信息

• A simple, stereospecific synthesis of dl-muscarine and dl-allomuscarine
  作者：T. Matsumoto、A. Ichihara、N. Ito

  DOI：10.1016/s0040-4020(01)83096-9

  日期：——

  A bromolactone (VII) was stereospecifically converted to a tetrabydrofuran (IVa, Me/CO2H cis) and a dimethylamide (VIII, Me/CONMe2 trans. Possible mechanisms for these reactions are discussed. Since IVa and VIII have been transformed to dl-muscarine (I) and dl-allomuscarine (II) respectively, stereospecific formation of IVa and VIII provides a stereospecific synthesis of these muscarines.

  将溴内酯（VII）立体定向转化为四氢呋喃（IVa，Me / CO 2 H cis）和二甲基酰胺（VIII，Me / CONMe 2 trans），讨论了这些反应的可能机理，因为IVa和VIII已转化为dl -毒蕈碱（I）和dl-铝肉碱（II），IVa和VIII的立体定向形成提供了这些毒蕈碱的立体定向合成。
• Chemoenzymic synthesis of the eight stereoisomeric muscarines
  作者：Marco De Amici、Carlo De Micheli、Giorgio Molteni、Davide Pitre、Giacomo Carrea、Sergio Riva、Sandro Spezia、Lucia Zetta

  DOI：10.1021/jo00001a015

  日期：1991.1

  Efficient syntheses of the eight stereoisomers of muscarine have been accomplished by dehydrogenase-catalyzed reduction of iodo ketones (+/-)-3a and (+/-)-3b. 3-alpha,20-beta-Hydroxysteroid dehydrogenase from Streptomyces hydrogenans exhibited high enantiomeric and diastereotopic selectivity for (+/-)-3a, yielding an equimolar mixture of iodo alcohol (-)-4 (2S,4S,5S) (96% ee) and iodo ketone (+)-3a (2R,5R) (96% ee) which was reduced by sodium borohydride to a mixture of (+)-4 and (+)-5. 3-beta,17-beta-Hydroxysteroid dehydrogenase from Pseudomonas testosteroni reduced (+/-)-3b with high diastereotopic selectivity to give an equimolar mixture of iodo alcohols (+)-6 (2R,4S,5S) (> 99% ee) and (-)-7 (2S,4S,5R) (81% ee). Synthesis of the remaining iodo alcohols [(-)-5, (-)-6, and (+)-7] was achieved by applying the Mitsunobu procedure to (-)-4, (-)-7, and (+)-6. The enantiomeric excess of intermediates 4-7 was determined by HPLC analysis of the (R)-(+)-MTPA esters. The chiral iodo alcohols 4-7 were then transformed into the final derivatives by conventional chemical manipulations.
• Eugster et al., Helvetica Chimica Acta, 1958, vol. 41, p. 583,586
  作者：Eugster et al.

  DOI：——

  日期：——
• Matsumoto; Maekawa, Angewandte Chemie, 1958, vol. 70, p. 507
  作者：Matsumoto、Maekawa

  DOI：——

  日期：——