(1S,2R,6S,7R)-1-((4S,5S)-4,5-Dimethyl-[1,3]dioxolan-2-yl)-4,10-dioxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione | 185678-74-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: (1S,2R,6S,7R)-1-((4S,5S)-4,5-Dimethyl-[1,3]dioxolan-2-yl)-4,10-dioxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione
• 英文别名: (1S,2R,6S,7R)-1-[(4S,5S)-4,5-dimethyl-1,3-dioxolan-2-yl]-4,10-dioxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
• CAS: 185678-74-4
• 化学式: C₁₃H₁₄O₆
• 分子量: 266.251
• InChiKey: ZNAIGZKAPNRSLT-RTVMLRSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2R,6S,7R)-1-((4S,5S)-4,5-Dimethyl-[1,3]dioxolan-2-yl)-4,10-dioxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到[(1S,2S,3R,4R)-1-((4S,5S)-4,5-Dimethyl-[1,3]dioxolan-2-yl)-3-hydroxymethyl-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-methanol
  参考文献：
  名称：

  Enantiomerically pure Diels-Alder adducts of maleic anhydride to furfural acetals through thermodynamic control. Single crystal and molecular structure of (1S,4R,4′S,5′S)-1-(4′,5′-dimethyldioxolan-2′-yl)-5,6-dimethylidene-7-oxabicyclo[2.2.1]hept-2-ene

  摘要：

  The acetal of (2S;,3S)-butane-2,3-diol and furfural is equilibrated in molten maleic anhydride with one major crystalline product which is a 1:1 complex of maleic anhydride and (1S,2R,3S,4R,4'S,5'S)-1-(4',5'-dimethyldioxolan-2'-yl)-7-oxabicyclo [2.2.1]hept-5-ene-2-exo,3-exo-dicarboxylic anhydride. This compound was converted into (1S,4R,4'S,5'S)-1-(4',5'-dimethyldioxolan-2'-yl)-5,6-dimethylidene-7-oxabicyclo[2.2.1]hept-2-ene (+)-12, the circular dichroism spectrum of which suggests a slightly skew s-cis-butadiene chromophore as confirmed by X-ray diffraction. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00417-x
• 作为产物：
  描述：

  (1S,2R,6S,7R)-1-((4S,5S)-4,5-Dimethyl-[1,3]dioxolan-2-yl)-4,10-dioxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione; compound with furan-2,5-dione 在 天然橡胶 作用下， 反应 24.0h， 以60%的产率得到(1S,2R,6S,7R)-1-((4S,5S)-4,5-Dimethyl-[1,3]dioxolan-2-yl)-4,10-dioxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione
  参考文献：
  名称：

  Enantiomerically pure Diels-Alder adducts of maleic anhydride to furfural acetals through thermodynamic control. Single crystal and molecular structure of (1S,4R,4′S,5′S)-1-(4′,5′-dimethyldioxolan-2′-yl)-5,6-dimethylidene-7-oxabicyclo[2.2.1]hept-2-ene

  摘要：

  The acetal of (2S;,3S)-butane-2,3-diol and furfural is equilibrated in molten maleic anhydride with one major crystalline product which is a 1:1 complex of maleic anhydride and (1S,2R,3S,4R,4'S,5'S)-1-(4',5'-dimethyldioxolan-2'-yl)-7-oxabicyclo [2.2.1]hept-5-ene-2-exo,3-exo-dicarboxylic anhydride. This compound was converted into (1S,4R,4'S,5'S)-1-(4',5'-dimethyldioxolan-2'-yl)-5,6-dimethylidene-7-oxabicyclo[2.2.1]hept-2-ene (+)-12, the circular dichroism spectrum of which suggests a slightly skew s-cis-butadiene chromophore as confirmed by X-ray diffraction. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00417-x

文献信息

• Enantiomerically pure Diels-Alder adducts of maleic anhydride to furfural acetals through thermodynamic control. Single crystal and molecular structure of (1S,4R,4′S,5′S)-1-(4′,5′-dimethyldioxolan-2′-yl)-5,6-dimethylidene-7-oxabicyclo[2.2.1]hept-2-ene
  作者：Antonio Guidi、Viviane Theurillat-Moritz、Pierre Vogel、A.Alan Pinkerton

  DOI：10.1016/0957-4166(96)00417-x

  日期：1996.11

  The acetal of (2S;,3S)-butane-2,3-diol and furfural is equilibrated in molten maleic anhydride with one major crystalline product which is a 1:1 complex of maleic anhydride and (1S,2R,3S,4R,4'S,5'S)-1-(4',5'-dimethyldioxolan-2'-yl)-7-oxabicyclo [2.2.1]hept-5-ene-2-exo,3-exo-dicarboxylic anhydride. This compound was converted into (1S,4R,4'S,5'S)-1-(4',5'-dimethyldioxolan-2'-yl)-5,6-dimethylidene-7-oxabicyclo[2.2.1]hept-2-ene (+)-12, the circular dichroism spectrum of which suggests a slightly skew s-cis-butadiene chromophore as confirmed by X-ray diffraction. Copyright (C) 1996 Elsevier Science Ltd