(1S,4R,4'S,5'S)-1-(4',5'-dimethyldioxolan-2'-yl)-5,6-dimethylidene-7-oxabicyclo[2.2.1]hept-2-ene | 185678-87-9

• 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: (1S,4R,4'S,5'S)-1-(4',5'-dimethyldioxolan-2'-yl)-5,6-dimethylidene-7-oxabicyclo[2.2.1]hept-2-ene
• 英文别名: (1S,4R)-1-[(4S,5S)-4,5-dimethyl-1,3-dioxolan-2-yl]-5,6-dimethylidene-7-oxabicyclo[2.2.1]hept-2-ene
• CAS: 185678-87-9
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: AIMCESLHIXGFCK-KQXIARHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(p-nitrobenzoyloxy)-3-buten-2-one 、 (1S,4R,4'S,5'S)-1-(4',5'-dimethyldioxolan-2'-yl)-5,6-dimethylidene-7-oxabicyclo[2.2.1]hept-2-ene 在 air 作用下， 生成 4-Nitro-benzoic acid (R)-2-acetyl-5,8-dihydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl ester
  参考文献：
  名称：

  Remote control of Diels-Alder additions. Enantioselective synthesis of (2R)-1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl methyl ketone (Wong's anthracycline intermediate) from furfural

  摘要：

  The enantiomerically pure (1S,4R,4'S,5'S)-1-(4',5'-dimethyl-dioxolan-2'-yl)-5,6-dimethylidene-7-oxabicyclo[2.2.1 derived from the acetal of furfural and (2S,3S)-butane-2,3-diol underwent addition to 1-acetylvinyl para-nitrobenzoate in the presence of an excess of t-BuMe2SiOSO2CF3 to yield an 83:17 mixture of two diastereomeric products which was converted into (2R)-1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl methyl ketone. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00433-3
• 作为产物：
  描述：

  [(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 在 吡啶 、 六甲基磷酰三胺 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 (1S,4R,4'S,5'S)-1-(4',5'-dimethyldioxolan-2'-yl)-5,6-dimethylidene-7-oxabicyclo[2.2.1]hept-2-ene
  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
• Remote control of Diels-Alder additions. Enantioselective synthesis of (2R)-1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl methyl ketone (Wong's anthracycline intermediate) from furfural
  作者：Viviane Theurillat-Moritz、Antonio Guidi、Pierre Vogel

  DOI：10.1016/s0957-4166(97)00433-3

  日期：1997.10

  The enantiomerically pure (1S,4R,4'S,5'S)-1-(4',5'-dimethyl-dioxolan-2'-yl)-5,6-dimethylidene-7-oxabicyclo[2.2.1 derived from the acetal of furfural and (2S,3S)-butane-2,3-diol underwent addition to 1-acetylvinyl para-nitrobenzoate in the presence of an excess of t-BuMe2SiOSO2CF3 to yield an 83:17 mixture of two diastereomeric products which was converted into (2R)-1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl methyl ketone. (C) 1997 Elsevier Science Ltd.