(+/-)-epiallo-muscarine iodide | 104048-27-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-epiallo-muscarine iodide
• 英文别名: (+/-)-(4c-hydroxy-5c-methyl-(2rH)-tetrahydro-furfuryl)-trimethyl-ammonium; iodide；(+/-)-(4c-Hydroxy-5c-methyl-(2rH)-tetrahydro-furfuryl)-trimethyl-ammonium; Jodid；[(2S,4R,5R)-4-hydroxy-5-methyloxolan-2-yl]methyl-trimethylazanium;iodide
• CAS: 104048-27-3
• 化学式: C₉H₂₀NO₂*I
• 分子量: 301.168
• InChiKey: PMFYONXEPDMBPE-RVKMJUHISA-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

• 作为反应物：
  描述：

  (+/-)-epiallo-muscarine iodide 在 silver(I) chloride 作用下， 以 水 为溶剂， 生成 5-Epimuscarine (epiallomuscarine)
  参考文献：
  名称：

  Chelation-controlled synthesis of (.+-.)-muscarine

  摘要：

  DOI：

  10.1021/jo01304a056
• 作为产物：
  描述：

  2-Methyl-3-hydroxy-tetrahydrofuran-carbonsaeure-(5)-dimethylamid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 (+/-)-epiallo-muscarine iodide
  参考文献：
  名称：

  Chelation-controlled synthesis of (.+-.)-muscarine

  摘要：

  DOI：

  10.1021/jo01304a056

文献信息

• Acid - catalyzed rearrangement of butyl 2-0-acetyl-4,5-anhydro-3,6-dideoxy-hexaldonate. Synthesis of racemic epiallomuscarine and epimuscarine
  作者：Marek Chmielewski、Piotr Guzik、Bogumiła Hinjtze、Włodzimierz M. Daniewski

  DOI：10.1016/s0040-4020(01)91432-2

  日期：1985.1

  in the presence of SnCl4 underwent an intramolecular rearrangement to give 2,5-anhydro ester 7. On the other hand the lyxo epimeric epoxide 5 under the same conditions afforded esters 7 and 8. Ester 7 was transformed into racemic epiallomuscarine (12), whereas the isomer 8 into racemic epimuscarine (13).

  丁基2-O-乙酰基-4,5-脱水-3,6-二脱氧DL-低聚木糖-hexaldonate（4）中的SnCl存在4行的分子内重排以得到2,5-脱水酯7.在其他在相同条件下，将lyxo差向异构环氧化合物5得到酯7和8。酯7被转化为外消旋表alcaruscarine（12），而异构体8被转化为外消旋epimuscarine（13）。
• 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.
• DE, AMICI MARCO;DE, MICHELI CARLO;MOLTENI, GIORGIO;PITRE, DAVIDE;CARREA, +, J. ORG. CHEM., 56,(1991) N, C. 67-72
  作者：DE, AMICI MARCO、DE, MICHELI CARLO、MOLTENI, GIORGIO、PITRE, DAVIDE、CARREA, +

  DOI：——

  日期：——
• Eugster et al., Helvetica Chimica Acta, 1958, vol. 41, p. 705,710
  作者：Eugster et al.

  DOI：——

  日期：——
• Matsumoto; Ichihara, Biochemische Zeitschrift, 1959, vol. 331, p. 580
  作者：Matsumoto、Ichihara

  DOI：——

  日期：——