(2S,3S,4aS,8aR)-2,3-dimethoxy-2,3,7-trimethyl-2,3,8,8a-tetrahydro-4aH-1,4-benzodioxin-5-one | 1173195-43-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4aS,8aR)-2,3-dimethoxy-2,3,7-trimethyl-2,3,8,8a-tetrahydro-4aH-1,4-benzodioxin-5-one
• 英文别名: (1R,2S)-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-5-methyl-3-oxo-4-cyclohexene；(2S,3S,4aS,8aR)-2,3-dimethoxy-2,3,7-trimethyl-8,8a-dihydro-4aH-1,4-benzodioxin-5-one
• CAS: 1173195-43-1
• 化学式: C₁₃H₂₀O₅
• 分子量: 256.299
• InChiKey: SDBAPNVYPHJFTK-NDBYEHHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4aS,8aR)-2,3-dimethoxy-2,3,7-trimethyl-2,3,8,8a-tetrahydro-4aH-1,4-benzodioxin-5-one 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 水 为溶剂， 以92%的产率得到(2S,3S,4aR,5R,8aR)-2,3-dimethoxy-2,3,7-trimethyl-4a,5,8,8a-tetrahydro-1,4-benzodioxin-5-ol
  参考文献：
  名称：

  Synthesis of polyhydroxy 7- and N-alkyl-azepanes as potent glycosidase inhibitors

  摘要：

  An effective synthetic method for polyhydroxylated azepanes that contain an alkyl group (Me or Bu) at either the 7- or N-positions is developed. The synthetic routes are accomplished in eight to ten steps from D-(-)-quinic acid. Among the compounds synthesized, the polyhydroxy 7-butyl azepane (compound 3), which possessed the R-configuration at C-7 position, is shown to give potent inhibition against beta-galactosidase (IC50 = 3 mu M). Preliminary biological data indicate that the length of alkyl groups along with the proper stereochemistry at the C-7 position is essential for acquiring extra binding affinity. Using similar synthetic routes, the polyhydroxy N-methyl and N-butyl azepanes are synthesized for the comparison of their biological activities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.11.014
• 作为产物：
  描述：

  (2R,3S,4aR,8aR)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,8a-tetrahydro-1,4-benzodioxin-6(5H)-one 在 cerium(III) chloride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2S,3S,4aS,8aR)-2,3-dimethoxy-2,3,7-trimethyl-2,3,8,8a-tetrahydro-4aH-1,4-benzodioxin-5-one
  参考文献：
  名称：

  Synthesis of polyhydroxy 7- and N-alkyl-azepanes as potent glycosidase inhibitors

  摘要：

  An effective synthetic method for polyhydroxylated azepanes that contain an alkyl group (Me or Bu) at either the 7- or N-positions is developed. The synthetic routes are accomplished in eight to ten steps from D-(-)-quinic acid. Among the compounds synthesized, the polyhydroxy 7-butyl azepane (compound 3), which possessed the R-configuration at C-7 position, is shown to give potent inhibition against beta-galactosidase (IC50 = 3 mu M). Preliminary biological data indicate that the length of alkyl groups along with the proper stereochemistry at the C-7 position is essential for acquiring extra binding affinity. Using similar synthetic routes, the polyhydroxy N-methyl and N-butyl azepanes are synthesized for the comparison of their biological activities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.11.014

文献信息

• Total Synthesis of Neoaltenuene
  作者：Martina Altemöller、Joachim Podlech

  DOI：10.1002/ejoc.200900125

  日期：2009.5

  The total synthesis of neoaltenuene, a toxin produced by alternaria fungi, has been achieved for the first time in 14 steps in a yield of 10 % starting from quinic acid and phloroglucinic acid, the longest linear sequence consisting of 10 steps. The key reaction was a palladium-catalyzed Suzuki-type coupling of an arene boronate with an iodinated cyclohexene.4a-epi-Neoaltenuene, a non-natural isomer

  由链格孢属真菌产生的毒素新烯烃的全合成首次以奎尼酸和间苯三甲酸为起始原料，分 14 步完成，产率为 10%，最长的线性序列由 10 步组成。关键反应是钯催化的芳烃硼酸酯与碘化环己烯的 Suzuki 型偶联。4a-epi-Neoaltenuene，一种非天然异构体也已类似地合成。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Synthesis of polyhydroxy 7- and N-alkyl-azepanes as potent glycosidase inhibitors
  作者：Tzenge-Lien Shih、Ming-Tsung Liang、Kuen-Da Wu、Chun-Hung Lin

  DOI：10.1016/j.carres.2010.11.014

  日期：2011.2

  An effective synthetic method for polyhydroxylated azepanes that contain an alkyl group (Me or Bu) at either the 7- or N-positions is developed. The synthetic routes are accomplished in eight to ten steps from D-(-)-quinic acid. Among the compounds synthesized, the polyhydroxy 7-butyl azepane (compound 3), which possessed the R-configuration at C-7 position, is shown to give potent inhibition against beta-galactosidase (IC50 = 3 mu M). Preliminary biological data indicate that the length of alkyl groups along with the proper stereochemistry at the C-7 position is essential for acquiring extra binding affinity. Using similar synthetic routes, the polyhydroxy N-methyl and N-butyl azepanes are synthesized for the comparison of their biological activities. (C) 2010 Elsevier Ltd. All rights reserved.