2-(1-nitropropan-2-yl)-1,3-dioxolane | 94371-22-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 2-(1-nitropropan-2-yl)-1,3-dioxolane
• CAS: 94371-22-9
• 化学式: C₆H₁₁NO₄
• 分子量: 161.158
• InChiKey: PRGAXULETDYMAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-nitropropan-2-yl)-1,3-dioxolane 在 hexacarbonyl molybdenum 异氰酸苯酯 作用下， 以 水 、 乙腈 、 苯 为溶剂， 反应 15.0h， 生成 (Z)-3-amino-4-(1,3-dioxolan-2-yl)-1-(4-methoxyphenyl)pent-2-en-1-one
  参考文献：
  名称：

  由异恶唑合成吡喃-4-酮

  摘要：

  据报道由异恶唑合成单，二和三取代的吡喃-4-酮。异恶唑可以由容易获得的起始原料合成，并与Mo（CO）6进行还原裂解反应生成烯氨基酮中间体，然后在酸性条件下环化成吡喃-4-酮。

  DOI：

  10.1016/s0040-4039(02)00567-1
• 作为产物：
  描述：

  2-(2-Iodo-1-methylethyl)-1,3-dioxolane 在 间苯三酚 、 sodium nitrite 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以82%的产率得到2-(1-nitropropan-2-yl)-1,3-dioxolane
  参考文献：
  名称：

  An Enantioselective Approach to Furanoeremophilanes: (+)-9-Oxoeuryopsin

  摘要：

  An enantioselective total synthesis of the furanoeremophilane sesquiterpene (+)-9-oxoeuryopsin 1 is reported. The synthesis involves as a key step a copper(II) triflate catalyzed tandem asymmetric conjugate addition of AlMe3 to 2-methyl-2-cyclohexen-1-one with the Feringa (S,R,R)-phosphoramidite binaphthol ligand, followed by aldol condensation of the resulting aluminum enolate with 4-methyl-3-furaldehyde 4. This tandem transformation has not been previously reported with a 2-substituted-2-cyclohexen-1-one. Conventional functional group manipulations completed the synthesis.

  DOI：

  10.1021/jo400399q

文献信息

• A nitrile oxide based entry to 2,3-dihydropyran-4-ones. Synthesis of a protected version "compactin lactone" in racemic and optically active forms
  作者：Alan P. Kozikowski、Chun Sing Li

  DOI：10.1021/jo00206a010

  日期：1985.3
• KOZIKOWSKI, A. P.;LI, CHUN-SING, J. ORG. CHEM., 1985, 50, N 6, 778-785
  作者：KOZIKOWSKI, A. P.、LI, CHUN-SING

  DOI：——

  日期：——
• Synthesis of pyran-4-ones from isoxazoles
  作者：Chun-Sing Li、Edith Lacasse

  DOI：10.1016/s0040-4039(02)00567-1

  日期：2002.5

  A synthesis of mono-, di- and tri-substituted pyran-4-ones from isoxazoles is reported. The isoxazoles can be synthesized from readily available starting materials and undergo a reductive cleavage reaction with Mo(CO)6 to generate enamino ketone intermediates, which are then cyclized to pyran-4-ones under acidic conditions.

  据报道由异恶唑合成单，二和三取代的吡喃-4-酮。异恶唑可以由容易获得的起始原料合成，并与Mo（CO）6进行还原裂解反应生成烯氨基酮中间体，然后在酸性条件下环化成吡喃-4-酮。
• An Enantioselective Approach to Furanoeremophilanes: (+)-9-Oxoeuryopsin
  作者：Ana L. Silva、Rubén A. Toscano、Luis A. Maldonado

  DOI：10.1021/jo400399q

  日期：2013.6.7

  An enantioselective total synthesis of the furanoeremophilane sesquiterpene (+)-9-oxoeuryopsin 1 is reported. The synthesis involves as a key step a copper(II) triflate catalyzed tandem asymmetric conjugate addition of AlMe3 to 2-methyl-2-cyclohexen-1-one with the Feringa (S,R,R)-phosphoramidite binaphthol ligand, followed by aldol condensation of the resulting aluminum enolate with 4-methyl-3-furaldehyde 4. This tandem transformation has not been previously reported with a 2-substituted-2-cyclohexen-1-one. Conventional functional group manipulations completed the synthesis.