(Sulfonyldibenzene-2,1-diyl)bis(diphenylmethanol) | 22218-99-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (Sulfonyldibenzene-2,1-diyl)bis(diphenylmethanol)
• 英文别名: [2-[2-[hydroxy(diphenyl)methyl]phenyl]sulfonylphenyl]-diphenylmethanol
• CAS: 22218-99-1
• 化学式: C₃₈H₃₀O₄S
• 分子量: 582.72
• InChiKey: WBHSNLFAIDLFCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  43
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  83
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二苯甲酮 、 二苯砜 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以27%的产率得到(Sulfonyldibenzene-2,1-diyl)bis(diphenylmethanol)
  参考文献：
  名称：

  Surprising fenchone induced cyclization: synthesis of the new chiral diol biphenyl-2,2′-sulfone-3,3′-bisfenchol (BISFOL)

  摘要：

  The new chiral diol BISFOL (biphenyl-2,2'-sulfone-3,3'-bisfenchol) is surprisingly formed by cyclization of diphenylsulfone after treatment with n-buthyllithium at -78 degrees C and subsequent addition of (-)-fenchone. Formation of fenchyl alcohol as byproduct points to a Meisenheimer intermediate as primary cyclization product, which transfers lithium hydride yielding the cyclic sulfone. As a chiral and chelating ligand, BISFOL catalyzes enantioselective diorganozinc additions to aldehydes and forms with dimethylzinc an unprecedented, macrocyclic, dimeric methylzinc complex. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.089

文献信息

• Surprising fenchone induced cyclization: synthesis of the new chiral diol biphenyl-2,2′-sulfone-3,3′-bisfenchol (BISFOL)
  作者：Francis Soki、Jörg M. Neudörfl、Bernd Goldfuss

  DOI：10.1016/j.tet.2005.08.089

  日期：2005.10

  The new chiral diol BISFOL (biphenyl-2,2'-sulfone-3,3'-bisfenchol) is surprisingly formed by cyclization of diphenylsulfone after treatment with n-buthyllithium at -78 degrees C and subsequent addition of (-)-fenchone. Formation of fenchyl alcohol as byproduct points to a Meisenheimer intermediate as primary cyclization product, which transfers lithium hydride yielding the cyclic sulfone. As a chiral and chelating ligand, BISFOL catalyzes enantioselective diorganozinc additions to aldehydes and forms with dimethylzinc an unprecedented, macrocyclic, dimeric methylzinc complex. (c) 2005 Elsevier Ltd. All rights reserved.