2-(pyrid-4-ylmethyl)-1,3-dioxolane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(pyrid-4-ylmethyl)-1,3-dioxolane
• 英文别名: 4-((1,3-dioxolan-2-yl)methyl)pyridine；4-(1,3-dioxolan-2-ylmethyl)pyridine
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: AUFWXLMQFDXOJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(2-溴乙基)-1,3-二恶烷 、 potassium pyridine-4-trifluoroborate 在 乙二醇二甲醚溴化镍 、 4,7-二苯基-1,10-菲罗啉 、 lithium hexamethyldisilazane 作用下， 以 仲丁醇 为溶剂， 反应 16.0h， 以78%的产率得到2-(pyrid-4-ylmethyl)-1,3-dioxolane
  参考文献：
  名称：

  Nickel-Catalyzed Cross-Coupling of Potassium Aryl- and Heteroaryltrifluoroborates with Unactivated Alkyl Halides

  摘要：

  A method for the cross-coupling of alkyl electrophiles with various potassium aryl- and heteroaryltrifluoroborates has been developed. Nearly stoichiometric amounts of organoboron species could be employed to cross-couple a large variety of challenging heteroaryl nucleophiles. Several functional groups were tolerated on both the electrophilic and the nucleophilic partners. Chemoselective reactivity of C(sp(3))-Br bonds in the presence of C(sp(2))-Br bonds was achieved.

  DOI：

  10.1021/ol102717x

文献信息

• Direct Synthesis of Protected Arylacetaldehydes by Palladium-Tetra­phosphine-Catalyzed Arylation of Ethyleneglycol Vinylether
  作者：Henri Doucet、Maurice Santelli、Isabelle Kondolff

  DOI：10.1055/s-2004-829063

  日期：——

  Through the use of [PdCl(C3H5)]2/cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane as a catalyst, a range of aryl bromides undergo Heck reaction with ethyleneglycol vinylether to give regioselectively protected arylacetaldehydes in good yields. The β-arylation products were obtained in the range 93-98% selectivity with electron-poor aryl bromides. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered aryl bromides. The arylvinyl ethers intermediates undergo subsequent ketalization to give the corresponding 2-benzyl-1,3-dioxolane derivatives.

  通过使用[PdCl(C3H5)]2/cis,cis,cis-1,2,3,4-四（二苯基膦甲基）环戊烷作为催化剂，一系列溴苯类化合物在 Heck 反应中与乙二醇乙烯醚反应，以良好的产率得到区域选择性保护的芳基乙醛。β-芳基化产物在电子贫乏的溴苯类化合物中获得了93-98%的选择性。此外，该催化剂在低负载下也可使用，甚至适用于空间位阻的溴苯类化合物的反应。芳基乙烯醚中间体随后经历缩酮化反应，得到相应的2-苄基-1,3-二氧戊环衍生物。
• Direct Synthesis of Protected Arylacetaldehydes by Tetrakis(phosphane)palladium-Catalyzed Arylation of Ethyleneglycol Vinyl Ether
  作者：Isabelle Kondolff、Henri Doucet、Maurice Santelli

  DOI：10.1002/ejoc.200500540

  日期：2006.2

  A range of aryl bromides undergo Heck reaction with ethylene glycol vinyl ether, in the presence of [PdCl(C3H5)]2/cis,cis,cis-1,2,3,4-tetrakis[(diphenylphosphanyl)methyl]cyclopentane as catalyst, to give regioselectively protected arylacetaldehydes in good yields. The β-arylation products were obtained in with 93–100 % selectivity with electron-poor aryl bromides or heteroaryl bromides. Furthermore

  在[PdCl(C3H5)]2/cis,cis,cis-1,2,3,4-四[​​(二苯基膦基)甲基]环戊烷作为催化剂存在下，一系列芳基溴化物与乙二醇乙烯基醚发生Heck反应，以良好的产率得到区域选择性保护的芳基乙醛。用缺电子的芳基溴化物或杂芳基溴化物以 93-100% 的选择性获得 β-芳基化产物。此外，该催化剂可以在低负载下使用，甚至用于与位阻芳基溴化物的反应。芳基乙烯基醚中间体经过随后的缩酮化得到相应的 2-苄基-1,3-二氧戊环衍生物。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Nickel-Catalyzed Cross-Coupling of Potassium Aryl- and Heteroaryltrifluoroborates with Unactivated Alkyl Halides
  作者：Gary A. Molander、O. Andreea Argintaru、Ioana Aron、Spencer D. Dreher

  DOI：10.1021/ol102717x

  日期：2010.12.17

  A method for the cross-coupling of alkyl electrophiles with various potassium aryl- and heteroaryltrifluoroborates has been developed. Nearly stoichiometric amounts of organoboron species could be employed to cross-couple a large variety of challenging heteroaryl nucleophiles. Several functional groups were tolerated on both the electrophilic and the nucleophilic partners. Chemoselective reactivity of C(sp(3))-Br bonds in the presence of C(sp(2))-Br bonds was achieved.