2-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-acrylonitrile | 132820-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-acrylonitrile
• 英文别名: 2-[[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl]prop-2-enenitrile
• CAS: 132820-57-6
• 化学式: C₁₂H₁₇NO₄
• 分子量: 239.271
• InChiKey: NMLOVZBPQVZMGV-GWOFURMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-acrylonitrile 在 三氯化铁 、 sodium iodide 、 锌 作用下， 以 吡啶 、 二甲基亚砜 为溶剂， 反应 30.0h， 生成 2-[[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl]-5-[(2,2,2-trifluoroacetyl)amino]pentanamide
  参考文献：
  名称：

  Relationship Between Chemical Structure and Antileishmanial Effect of Sinefungine Analogues

  摘要：

  The synthesis of various analogues of sinefungin (1), having structures 2-5, has been developed by means of an original approach which uses radical chemistry. The study of their biological activities revealed that for the antileishmanial effect of sinefungin, the presence of the amino group at C-6' in the (S)-configuration and the presence of the carboxyl group at C-9' are necessary.

  DOI：

  10.1080/07328319608007381
• 作为产物：
  描述：

  methyl-5-deoxy-5-(diethoxyphosphinyl)cyanomethyl-2,3-O-isopropyliden-β-D-ribofuranoside 、 聚合甲醛 以85%的产率得到
  参考文献：
  名称：

  MOUNA, ABDEL MALEK;BLANCHARD, PIERRE;FOURREY, JEAN-LOUIS;ROBERT-GERO, MAL+, TETRAHEDRON LETT., 31,(1990) N8, C. 7003-7006

  摘要：

  DOI：

文献信息

• A conjugate addition of primary alkyl iodide derived species to electron deficient olefins
  作者：Pierre Blanchard、Mohammed S. El Kortbi、Jean-Louis Fourrey、Malka Robert-Gero

  DOI：10.1016/s0040-4039(00)92077-x

  日期：1992.6

  Efficient zinc/copper couple induced addition of carbohydrate or amino acid residues derived from their corresponding iodides to various activated olefins have been accomplished by simple vibromixing of the heterogenous reaction mixture.

  通过异质反应混合物的简单振动混合，已经实现了锌/铜对诱导的源自其相应碘化物的碳水化合物或氨基酸残基向各种活化烯烃的添加。
• Zinc-iron couple induced conjugate addition of alkyl halide derived radicals to activated olefins
  作者：Pierre Blanchard、Adilson D. Da Silva、Mohammed S. El Kortbi、Jean Louis Fourrey、Malka Robert-Gero

  DOI：10.1021/jo00075a066

  日期：1993.11
• MOUNA, ABDEL MALEK;BLANCHARD, PIERRE;FOURREY, JEAN-LOUIS;ROBERT-GERO, MAL+, TETRAHEDRON LETT., 31,(1990) N8, C. 7003-7006
  作者：MOUNA, ABDEL MALEK、BLANCHARD, PIERRE、FOURREY, JEAN-LOUIS、ROBERT-GERO, MAL+

  DOI：——

  日期：——
• Relationship Between Chemical Structure and Antileishmanial Effect of Sinefungine Analogues
  作者：P. Blanchard、M. S. El Kortbi、J. -L. Fourrey、F. Lawrence、M. Robert-Gero

  DOI：10.1080/07328319608007381

  日期：1996.6

  The synthesis of various analogues of sinefungin (1), having structures 2-5, has been developed by means of an original approach which uses radical chemistry. The study of their biological activities revealed that for the antileishmanial effect of sinefungin, the presence of the amino group at C-6' in the (S)-configuration and the presence of the carboxyl group at C-9' are necessary.