Methyl 6-(2-methyl-1,3-dioxolan-2-yl)hexanoate | 139117-55-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 6-(2-methyl-1,3-dioxolan-2-yl)hexanoate
• CAS: 139117-55-8
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: LSEHGTQIPYBRMF-UHFFFAOYSA-N

物化性质

• 沸点：
  266.0±15.0 °C(Predicted)
• 密度：
  1.016±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 6-(2-methyl-1,3-dioxolan-2-yl)hexanoate 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 甲苯 、 苯 为溶剂， 生成 (E)-9-Oxo-2-decanoic acid methyl ester
  参考文献：
  名称：

  A microbial synthesis of R and S-9-hydroxy-(E)-2-decenoic acid(9-HDA), a queen honeybee pheromone

  摘要：

  (R,E)-9-hydroxy-2-decenoic acid (9-HDA) and its (S.E)- isomer have been prepared by using an organic-microbial approach.

  DOI：

  10.1016/s0957-4166(00)86050-4
• 作为产物：
  描述：

  Dimethyl 2-acetylheptanedioate 在 potassium carbonate 、 苯硫酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 Methyl 6-(2-methyl-1,3-dioxolan-2-yl)hexanoate
  参考文献：
  名称：

  Diiodosilane. 4.¹Direct Reduction of Ketals and Acetals in the Presence of Unprotected Carbonyls. A Case of Inverted Chemoselectivity

  摘要：

  酮和醛可被二碘硅烷选择性地还原成碘烷。这种颠倒 "受保护 "和 "未受保护 "羰基的正常反应顺序的做法，可以部分还原多羰基化合物，并具有不同寻常的区域和化学选择性。 因此，8,8-(亚乙二氧基)辛烷-2-酮、7,7-(亚乙二氧基)辛醛、3,3-(亚乙二氧基)-雄甾烷-17-酮和 3,3-(亚乙二氧基)孕烷-11,20-二酮被转化为相应的碘化合物。

  DOI：

  10.1055/s-1991-26533

文献信息

• The first general method for α-trifluoromethylation of carboxylic acids using BrF₃
  作者：Aviv Hagooly、Shlomo Rozen

  DOI：10.1039/b315705a

  日期：——

  2-Carbomethoxy-1,1-bis(methylsulfide)-1-alkenes, easily made from carboxylic acids, CS2 and MeI, were treated with BrF3 producing eventually the desired α-trifluoromethyl carboxylate derivatives – RCH(CF3)COOR′ – in good yields.

  2-Carbomethoxy-1,1-bis(methylsulfide)-1-alkenes 很容易由羧酸、CS2 和 MeI 制成，用 BrF3 处理后，最终会以良好的收率生成所需的δ-三氟甲基羧酸衍生物 RCH(CF3)COORâ² 。
• Total synthesis of queen substance of honeybee using an organosilicon route
  作者：Moncef Bellassoued、Assieh Majidi

  DOI：10.1016/0040-4039(91)80490-w

  日期：1991.12

  O-Silylated enolates are used as the key intermediates in the total synthesis of queen substance. The synthesis proceeds in 7 steps and affords the desired pheromone with very high stereoselectivity and 34% overall yield.

  O-甲硅烷基化的烯酸酯被用作皇后物质全合成中的关键中间体。合成以7个步骤进行，并以非常高的立体选择性和34％的总收率提供了所需的信息素。
• Potentiation of cADPR-Induced Ca²⁺-Release by Methylxanthine Analogues
  作者：Rosaria A. Cavallaro、Luigi Filocamo、Annamaria Galuppi、Antony Galione、Mario Brufani、Armando A. Genazzani

  DOI：10.1021/jm980469t

  日期：1999.7.1

  Caffeine and other methylxanthines are known to induce Ca2+-release from intracellular stores via the ryanodine receptor. In the present work, a range of caffeine analogues, in which methyl groups at the 1 and 7 positions were replaced with alkyl chains containing different functional groups (oxo, hydroxyl, propargyl, ester, and acids), were synthesized. These compounds were then screened for their ability to potentiate Ca2+-release induced by cADPR (an endogenous modulator of ryanodine receptors) in sea urchin egg homogenates. Two of the synthesized methylxanthines, 1,3-dimethyl-7-(7-hydroxyoctyl)xanthine (37) and 3-methyl-7-(7-oxooctyl)-1-propargylxanthine (66), were shown to be more potent than caffeine in potentiating cADPR-induced Ca2+-release, while 1,3-dimethyl-7-(5-ethylcarboxypentyl)xanthine (14) was shown to be more efficacious. The development of new methylxanthine analogues may lead to a better understanding of ryanodine receptor function and could possibly provide novel therapeutic agents.
• General Method for the Preparation of β,β-Difluoroacrylates Using BrF₃
  作者：Aviv Hagooly、Shlomo Rozen

  DOI：10.1021/jo0485280

  日期：2004.12.1

  Various esters were reacted with base, carbon disulfide, and methyl iodide, producing 2-carboalkoxy1,1-bis(methyl sulfide)-1-alkenes (2). The reaction of 2 with BrF3, followed by oxidation with HOF-CH3CN gave the bromodifluorosulfonyl derivatives 5. Subsequent treatment with Raney nickel led to alpha-substituted beta,beta-difluoroacrylates 6 in overall yields of 50-80%.