(1R,2R,3R,4R)-1,2-O-Benzylideneconduritol E | 152877-69-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2R,3R,4R)-1,2-O-Benzylideneconduritol E
• 英文别名: (2R,3aS,4R,5R,7aR)-2-phenyl-3a,4,5,7a-tetrahydro-1,3-benzodioxole-4,5-diol
• CAS: 152877-69-5
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: JJQKXSBVGYXWOF-SYLRKERUSA-N

物化性质

• 沸点：
  427.5±45.0 °C(predicted)
• 密度：
  1.344±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R,4R)-1,2-O-Benzylideneconduritol E 在 Dowex-50W-X₈ (H⁽¹⁺⁾ form) 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以75%的产率得到(-)-conduritol E
  参考文献：
  名称：

  Asymmetric dihydroxylation of a meso-symmetric cyclic diene using AD-mix reagents: a new enantiocontrolled route to conduritol E

  摘要：

  The asymmetric dihydroxylation of two symmetric cyclohexa-1,3-diene derivatives, including a meso-symmetric substrate, has been investigated for the first time using the Sharpless AD-mix reagents. Although cyclohexa-1,3-diene, itself showed unsatisfactory enantioselectivity, meso-symmetric 1,2-O-benzylidene-cis-cyclohexa-3,5-diene-1,2-diol showed a practical level of enantioselectivity and furnished the optically active diol in good yield. The diol obtained could be transformed into optically pure (+)-conduritol E in good yield, after a single recrystallization. The stereochemical outcome of the dihydroxylation was in harmony with the observations so far reported.

  DOI：

  10.1021/jo00080a011
• 作为产物：
  描述：

  cis-1,2-dihydrocatechol 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 甲基磺酰胺 、 Sharpless AD-mix-α reagent 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 56.83h， 生成 (1R,2R,3R,4R)-1,2-O-Benzylideneconduritol E
  参考文献：
  名称：

  Asymmetric dihydroxylation of a meso-symmetric cyclic diene using AD-mix reagents: a new enantiocontrolled route to conduritol E

  摘要：

  The asymmetric dihydroxylation of two symmetric cyclohexa-1,3-diene derivatives, including a meso-symmetric substrate, has been investigated for the first time using the Sharpless AD-mix reagents. Although cyclohexa-1,3-diene, itself showed unsatisfactory enantioselectivity, meso-symmetric 1,2-O-benzylidene-cis-cyclohexa-3,5-diene-1,2-diol showed a practical level of enantioselectivity and furnished the optically active diol in good yield. The diol obtained could be transformed into optically pure (+)-conduritol E in good yield, after a single recrystallization. The stereochemical outcome of the dihydroxylation was in harmony with the observations so far reported.

  DOI：

  10.1021/jo00080a011

文献信息

• Asymmetric dihydroxylation of a meso-symmetric cyclic diene using AD-mix reagents: a new enantiocontrolled route to conduritol E
  作者：Seiichi Takano、Takehiko Yoshimitsu、Kunio Ogasawara

  DOI：10.1021/jo00080a011

  日期：1994.1

  The asymmetric dihydroxylation of two symmetric cyclohexa-1,3-diene derivatives, including a meso-symmetric substrate, has been investigated for the first time using the Sharpless AD-mix reagents. Although cyclohexa-1,3-diene, itself showed unsatisfactory enantioselectivity, meso-symmetric 1,2-O-benzylidene-cis-cyclohexa-3,5-diene-1,2-diol showed a practical level of enantioselectivity and furnished the optically active diol in good yield. The diol obtained could be transformed into optically pure (+)-conduritol E in good yield, after a single recrystallization. The stereochemical outcome of the dihydroxylation was in harmony with the observations so far reported.