2-octyl-[1,3]dioxane | 17357-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 2-octyl-[1,3]dioxane
• 英文别名: 2-Octyl-1,3-dioxan；2-Octyl-1,3-dioxane
• CAS: 17357-15-2
• 化学式: C₁₂H₂₄O₂
• 分子量: 200.321
• InChiKey: VTFSQYXRDREZAN-UHFFFAOYSA-N

物化性质

• 沸点：
  80-82 °C(Press: 0.2 Torr)
• 密度：
  0.889±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-octyl-[1,3]dioxane 在 四乙基溴化铵 、 水 、 2-碘酰基苯甲酸 作用下， 反应 1.0h， 以86%的产率得到3-hydoxypropyl nonanoate
  参考文献：
  名称：

  2-碘氧基苯甲酸/溴化四乙铵/水：乙醛的氧化裂解的有效组合

  摘要：

  已经开发出一种简单有效的方法，用于将环状和非环状缩醛分别氧化为相应的羟烷基羧酸酯和简单酯。在四乙基溴化铵存在下，将2-碘氧基苯甲酸（IBX）用于水性介质中的反应。该方案的显着特征包括反应时间短，对环境无害的试剂和溶剂以及中等至高产率。 邻碘氧苯甲酸-缩醛-氧化-羟烷基酯-醇

  DOI：

  10.1055/s-0028-1087986
• 作为产物：
  描述：

  壬醛 、 1,3-丙二醇 在 ruthenium trichloride 、 sodium sulfate 作用下， 反应 10.0h， 以85%的产率得到2-octyl-[1,3]dioxane
  参考文献：
  名称：

  A convenient and highly efficient method for the protection of aldehydes using very low loading hydrous ruthenium(III) trichloride as catalyst

  摘要：

  A convenient method for the chemoselective protections of both aliphatic and aromatic aldehydes has been developed. Ruthenium(III) trichloride (0.1 mol%) has found to be an highly efficient catalyst in the acetalizations of aldehydes with various simple alcohols such as methanol, ethanol, or diols such as 1,2-ethylanediol and 1,3-propanediol under mild reaction conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.112

文献信息

• Electrochemical Oxidation of 1-Phenylthio-1-trimethylsilylalkanes
  作者：Jun-ichi Yoshida、Sachihiko Isoe

  DOI：10.1246/cl.1987.631

  日期：1987.4.5

  Electrochemical oxidation of 1-phenylthio-1-trimethylsilylalkanes in the presence of alcohol resulted in facile cleavage of the carbon–silicon bond and formation of the corresponding acetals.

  在醇存在下，1-苯硫基-1-三甲基硅基烷的电化学氧化导致碳-硅键的容易断裂，并形成相应的缩醛。
• Formation of Acetals under Rhodium-Catalyzed Hydroformylation Conditions in Alcohols
  作者：Olivier Diebolt、Clément Cruzeuil、Christian Müller、Dieter Vogt

  DOI：10.1002/adsc.201100707

  日期：2012.3

  Hydroformylation of terminal alkenes in alcohol solvents leads to the selective formation of the corresponding acetals. The Xantphos ligand gave the best results as well as acetal selectivities higher than 99% and linear/branched ratios of up to 52 were obtained. The scope of the reaction was studied. Acetals were found to be unreactive under hydroaminomethylation conditions.

  在醇溶剂中末端烯烃的加氢甲酰化导致相应缩醛的选择性形成。Xantphos配体提供了最佳结果，乙缩醛选择性高于99％，线性/支化比高达52。研究了反应范围。发现缩醛在氢氨甲基化条件下不反应。
• New one carbon homologation reagents utilizing electrochemical oxidation of organosilicon compounds
  作者：Jun-ichi Yoshida、Shin-ichiro Matsunaga、Toshiki Murata、Sachihiko Isoe

  DOI：10.1016/s0040-4020(01)87051-4

  日期：1991.1

  Phenylthio(trimethylsilyl)methane, phenylthiosbis(trimethylsily)methane, methoxy(trimethysily)methane, and methoxybis(trimethylsilyl)methane are depronated and the resulting anions are alkylated with electrophiles such as organic halides. The alkylation products are readily converted into the corresponding dimethyl acetals or methyl esters by electrochemical oxidation in methanol.
• Lee, Yuh-Shan; Valle ,Luis del; Larson, Gerald L., Synthetic Communications, 1987, vol. 17, # 4, p. 385 - 392
  作者：Lee, Yuh-Shan、Valle ,Luis del、Larson, Gerald L.

  DOI：——

  日期：——
• Tandem hydroformylation–acetalization with a ruthenium catalyst immobilized in ionic liquids
  作者：Jakob Norinder、Claudia Rodrigues、Armin Börner

  DOI：10.1016/j.molcata.2014.04.009

  日期：2014.9

  For the first time, a ruthenium catalyzed hydroformylation acetalization reaction of olefins is presented. The tandem reaction proceeds well with 1,2- or 1,3-diols, trapping the intermediary formed aldehydes as cyclic acetals. In this manner the hydrogenation of the aldehydes to the corresponding alcohols usually observed with Ru catalysts is prevented. The optimized catalytic system consisting of Ru catalyst, ionic liquids, acetic acid and ammonium salt can be recycled and reused for at least two further runs. Interestingly, styrenes as substrate give preferentially terminal acetals. (C) 2014 Elsevier B.V. All rights reserved.