6β,7β-dihydroxy-8-methyl-8-azabicyclo<3.2.1>octan-3-one | 575-63-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: 6β,7β-dihydroxy-8-methyl-8-azabicyclo<3.2.1>octan-3-one
• 英文别名: 6exo,7exo-dihydroxy-tropan-3-one；6exo,7exo-Dihydroxy-tropan-3-on；teloidinone；(1R,5S,6S,7R)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-one
• CAS: 575-63-3
• 化学式: C₈H₁₃NO₃
• 分子量: 171.196
• InChiKey: BBZXQEXUIOSPAN-KVFPUHGPSA-N

物化性质

• 熔点：
  192 °C
• 沸点：
  343.1±41.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6β,7β-dihydroxy-8-methyl-8-azabicyclo<3.2.1>octan-3-one 在 sodium tetrahydroborate 、 cerium(III) chloride 、 三氟乙酸 作用下， 生成 9-methyl-2-methoxyhexahydro-6H-cyclohepta-1,3-dioxol-4,8-imin-6-ol
  参考文献：
  名称：

  UNIVERSAL SOLID SUPPORTS AND PHOSPHORAMIDITE BUILDING BLOCKS FOR OLIGONUCLEOTIDE SYNTHESIS

  摘要：

  Disclosed herein are chemical preparation of oligonucleotides, chemical entities useful in such preparation, processes for such preparation, and methods of use relating to the chemical preparation of oligonucleotides. Further disclosed herein are novel universal solid supports and phosphoramidite building blocks for oligonucleotide synthesis on solid phase that effect the removal of the 3'-phosphate moieties during the course of oligonucleotide deprotection.

  公开号：

  WO2024044792A1
• 作为产物：
  描述：

  1,3-丙酮二羧酸 、 erythro-tetrodialdose 、 甲胺 生成 6β,7β-dihydroxy-8-methyl-8-azabicyclo<3.2.1>octan-3-one
  参考文献：
  名称：

  The Synthesis of Teloidinone and 6-Hydroxytropinone

  摘要：

  DOI：

  10.1021/ja01135a032

文献信息

• <i>C</i>-Nucleosides and related compounds. XIV. The synthesis of a nitrogen analogue of showdomycin
  作者：George Just、G. Paul Donnini

  DOI：10.1139/v77-417

  日期：1977.8.15

  Starting from teloidinone 5a, 2-(2′α,3′α-dihydroxy-4′β-hydroxymethyl-N-carbomethoxypyrrolidin-1β-yl)maleimide 1b, a showdomycin analogue in which the ribofuranosyl ring oxygen is replaced by an N-carbomethoxy group, has been synthesized in 7% overall yield.

  从 teloidinone 5a 开始，2-(2'α,3'α-dihydroxy-4'β-hydroxymethyl-N-carbomethoxypyrrolidin-1β-yl)maleimide 1b，一种显示霉素类似物，其中呋喃核糖环氧被 N-取代碳甲氧基，总产率为 7%。
• Synthesis and stereochemistry of (3α)-6β,7β-dihydroxy- and 6β-hydroxy-8-alkyl-8-azabicyclo[3.2.1]octane-3-spiro-5′-imidazoline-2′,4′-diones
  作者：Mercedes Villacampa、Manuel Martínez、Gregorio González-Trigo、Mó Nica M. Söllhuber

  DOI：10.1002/jhet.5570290628

  日期：1992.10

  The synthesis of 6β-hydroxy- and 6β,7β-dihydroxy-8-alkyl-8-azabicyclo[3.2.1]octane-3-spiro-5′-hydantoins was stereoselectively achieved by Bucherer-Bergs reaction of the corresponding ketones. An α configuration on C3 was proposed for all hydantoins on the basis of spectral data.

  通过相应酮的Bucherer-Bergs反应立体选择性地合成了6β-羟基-和6β，7β-二羟基-8-烷基-8-氮杂双环[3.2.1]辛烷-3-螺-5'-乙内酰脲。在光谱数据的基础上，对所有乙内酰脲提出在C 3上的α构型。
• Access to 2-Alkyltropones via Organic Base-Catalyzed Tandem Deamination and Aldol Condensation of Tropinone-Derived Quaternary Ammonium Salts
  作者：Yan Wang、Qian-Qian Wu、Shi-Kai Tian

  DOI：10.1021/acs.joc.3c01983

  日期：2023.12.1

  The tropone skeleton exists in a number of natural products and bioactive substances, and currently, the applications of substituted tropones are significantly limited by their preparative methods. Herein, we report a very convenient method to access 2-alkyltropones via organic base-catalyzed tandem reaction of tropinone-derived quaternary ammonium salts. Tropinone methiodide reacted with a wide variety

  托酮骨架存在于许多天然产物和生物活性物质中，目前，取代托酮的应用受到其制备方法的严重限制。在此，我们报道了一种非常方便的方法，通过托品酮衍生的季铵盐的有机碱催化串联反应来获得 2-烷基托酮。托品酮甲碘化物在 1,4-二氮杂双环[2.2.2]辛烷存在下与多种芳香族和脂肪族醛反应，以中等至优异的产率和极高的位点选择性提供结构多样的 2-烷基托酮。该反应采用现成的原料和试剂，不含过渡金属，与水和空气相容，可耐受多种官能团，并且可以轻松扩大规模。此外，该产品适合各种合成转化。初步机理研究表明，该反应通过串联脱氨、羟醛缩合和异构化进行。
• Schoepf; Arnold, Justus Liebigs Annalen der Chemie, 1947, vol. 558, p. 109,123
  作者：Schoepf、Arnold

  DOI：——

  日期：——
• Zeile; Heusner, Chemische Berichte, 1957, vol. 90, p. 2800,2805
  作者：Zeile、Heusner

  DOI：——

  日期：——