(+/-)-4-(3-cyanopropyl)-2,2-dimethyldioxolane | 132619-82-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-4-(3-cyanopropyl)-2,2-dimethyldioxolane
• 英文别名: (+/-)-5,6-O-isopropylidenehexanenitrile；5,6-isopropylidenedioxyhexanonitrile；2,2-Dimethyl-1,3-dioxolane-4-butanenitrile；4-(2,2-dimethyl-1,3-dioxolan-4-yl)butanenitrile
• CAS: 132619-82-0
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: WBUXGNPHKATBOR-UHFFFAOYSA-N

物化性质

• 沸点：
  263.4±15.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-4-(3-cyanopropyl)-2,2-dimethyldioxolane 在 敌草腈 、 sodium acetate 、 sodium hydride 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 36.0h， 生成 3-(N-ethoxycarbonyl)cyanomethyleneamino-2-(3,4-isopropylidenedioxybutyl)acrylonitrile
  参考文献：
  名称：

  Buchanan, J. Grant; Craven, David A.; Wightman, Richard H., Journal of the Chemical Society. Perkin transactions I, 1991, # 1, p. 195 - 202

  摘要：

  DOI：
• 作为产物：
  描述：

  5-己烯腈 在 四氧化锇 、 对甲苯磺酸 、 氧化-4-甲基吗啉一水合物 作用下， 以 水 、 丙酮 为溶剂， 反应 24.0h， 生成 (+/-)-4-(3-cyanopropyl)-2,2-dimethyldioxolane
  参考文献：
  名称：

  Raadt, Anna de; Klempier, Norbert; Faber, Kurt, Journal of the Chemical Society. Perkin transactions I, 1992, # 1, p. 137 - 140

  摘要：

  DOI：

文献信息

• Selective transformation of nitriles into amides and carboxylic acids by an immobilized nitrilase
  作者：Norbert Klempier、Anna de Raadt、Kurt Faber、Herfried Griengl

  DOI：10.1016/s0040-4039(00)92623-6

  日期：1991.1

  Using an immobilized nitrilase from Rhodococcus sp. mild and selective hydrolysis of nitriles can be achieved even in the presence of acid or base sensitive groups under neutral conditions. This method is applicable to a broad range of substrates as exemplified by aliphatic, alicyclic, heterocyclic and carbohydrate type nitriles.

  使用来自红球菌属的固定化腈水解酶。即使在中性条件下存在酸或碱敏感基团，也可以实现腈的温和选择性水解。该方法适用于各种底物，例如脂族，脂环族，杂环和碳水化合物类腈。
• Deoxygenative Transformation of Alcohols via Phosphoranyl Radical from Exogenous Radical Addition
  作者：Wenhao Xu、Chao Fan、Xile Hu、Tao XU

  DOI：10.1002/anie.202401575

  日期：2024.4.22

  A general approach to the direct deoxygenative transformation of primary, secondary, and tertiary alcohols has been developed. It proceeds through phosphoranyl radical intermediates generated by the addition of exogenous iodine radical to trivalent alkoxylphosphanes. Since these alkoxylphosphanes are readily in situ obtained from alcohols and commercially available, inexpensive chlorodiphenylphosphine

  已经开发出伯醇、仲醇和叔醇直接脱氧转化的通用方法。它通过将外源碘自由基加成到三价烷氧基膦上而生成正膦基中间体来进行。由于这些烷氧基膦很容易从醇和市售廉价的氯二苯基膦原位获得，因此可以利用具有各种官能团的各种醇与烯烃或芳基碘化物进行脱氧交叉偶联。该方法还证明了多羟基底物的选择性转化和复杂有机分子的快速合成。
• Diastereo- and enantioselective routes to some 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols. Absolute stereochemistry of (E,E,E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-3-ol and of (E,E)-8-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)methanol present in Bactrocera cucumis
  作者：Michael V. Perkins、Mark F. Jacobs、William Kitching、Peter J. Cassidy、Judith A. Lewis、Richard A. I. Drew

  DOI：10.1021/jo00038a027

  日期：1992.6

  Routes to the four regioisomeric 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols have been developed, and in the racemic series, mercury(II)-mediated reactions of appropriate dienone, hydroxy enone, dienedione, and hydroxy dienone systems have been exploited. Most of the epimeric pairs of alcohols (i.e. axial or equatorial) in the E,E, E,Z, or Z,E spiroacetal ring systems have been characterized by detailed H-1, C-13, and correlated NMR spectroscopy and mass spectrometry. Key enantiomers of these alcohols have been obtained by elaborating chiral starting materials such as D-mannitol, L-arabinose, poly(hydroxybutyrate), and in the case of the 5-hydroxy derivative, mandelonitrile lyase mediated formation of a key chiral cyanohydrin was employed. Most of the alcohols, as their trifluoroacetates, are resolved (into enantiomers) on a Lipodex A GC column, thus facilitating their identification from natural sources. In this way, the absolute configurations of a number of 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols present in the rectal gland secretion of Bactrocera cucumis (cucumber fly) have been determined.
• BUCHANAN, J. GRANT;CRAVEN, DAVID A.;WIGHTMAN, RICHARD H.;HARNDEN, MICHAEL+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1991) N, C. 195-202
  作者：BUCHANAN, J. GRANT、CRAVEN, DAVID A.、WIGHTMAN, RICHARD H.、HARNDEN, MICHAEL+

  DOI：——

  日期：——