6,6'-bis(hydroxymethyl)-5,5'-bi-1,3-benzodioxole | 79422-40-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 6,6'-bis(hydroxymethyl)-5,5'-bi-1,3-benzodioxole
• 英文别名: 6,6'-bis(5-hydroxymethyl-1,3-benzodioxole)；[5,5'-Bi-1,3-benzodioxole]-6,6'-dimethanol；[6-[6-(hydroxymethyl)-1,3-benzodioxol-5-yl]-1,3-benzodioxol-5-yl]methanol
• CAS: 79422-40-5
• 化学式: C₁₆H₁₄O₆
• 分子量: 302.284
• InChiKey: KNNPVLGXUKWPMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4'-溴乙酰苯胺 在 bis(1,5-cyclooctadiene)nickel (0) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 以15%的产率得到6,6'-bis(hydroxymethyl)-5,5'-bi-1,3-benzodioxole
  参考文献：
  名称：

  Reaction of aryl and vinyl halides with zerovalent nickel - preparative aspects and the synthesis of alnusone

  摘要：

  DOI：

  10.1021/ja00411a034

文献信息

• Intramolecular biaryl coupling reaction of benzyl benzoate and phenyl benzoate derivatives, and its application to the formal synthesis of (−)-steganone
  作者：Shigemitsu Takeda、Hitoshi Abe、Yasuo Takeuchi、Takashi Harayama

  DOI：10.1016/j.tet.2006.10.059

  日期：2007.1

  Construction of the biaryl moiety of stegane and related compounds through an intramolecular biaryl coupling reaction is described. Undesired products were obtained by the intramolecular coupling reaction of benzyl benzoates (8, 13, and 14) because of their steric and electrostatic properties, and only that of phenyl benzoates (26b and 26c) afforded the desired biaryl lactones in good yields. An asymmetric

  描述了通过分子内联芳基偶合反应构建硬脂烷和相关化合物的联芳基部分。不希望的产物通过苄基苯甲酸酯（的分子内偶合反应得到8，13，和14，因为它们的空间和静电性质），并且只有苯基苯甲酸酯（的26B和26C，得到所需的二芳基内酯以良好产率）。使用对映选择性内酯开放反应，然后四步转化为已知化合物，已经实现了标题化合物的不对称形式合成。
• An Attempt for Biaryl Coupling Reaction of Benzyl Benzoate Derivatives under Ullmann Conditions
  作者：Hitoshi Abe、Shigemitsu Takeda、Yasuo Takeuchi、Takashi Harayama

  DOI：10.3987/com-03-s13

  日期：——

  The biaryl coupling reaction of benzyl benzoate derivatives (3) and (4) was examined with copper(0) reagent. A dimerized product (9) was mainly obtained whereas the desired intramolecularly coupled product (11) was not detected when 3 was employed as the substrate. On the other hand, the reaction of 4 afforded a small amount of the desired lactone (14) although the main product was the dimerized 12.
• Reaction of aryl and vinyl halides with zerovalent nickel - preparative aspects and the synthesis of alnusone
  作者：M. F. Semmelhack、Paul Helquist、L. D. Jones、Leonard Keller、L. Mendelson、Laurine Speltz Ryono、Janice Gorzynski Smith、R. D. Stauffer

  DOI：10.1021/ja00411a034

  日期：1981.10