biphenyl-2,2'-sulfone-3,3'-bisfenchol | 870294-00-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: biphenyl-2,2'-sulfone-3,3'-bisfenchol
• 英文别名: (1R,2R,4S)-2-[6-[(1R,2R,4S)-2-hydroxy-1,3,3-trimethyl-2-bicyclo[2.2.1]heptanyl]-5,5-dioxodibenzothiophen-4-yl]-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 870294-00-1
• 化学式: C₃₂H₄₀O₄S
• 分子量: 520.733
• InChiKey: AKVRBNGQGFVEQI-XFEZTCCASA-N

物化性质

• 熔点：
  >283 °C (decomp)(Solv: dichloromethane (75-09-2); ethanol (64-17-5))
• 沸点：
  666.9±50.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  37
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  83
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  biphenyl-2,2'-sulfone-3,3'-bisfenchol 、 三甲基铝 以 甲苯 为溶剂， 以65%的产率得到tetramethylaluminumbiphenylether-2,2'-sulfone-3,3'-bisfencholate
  参考文献：
  名称：

  Homo- vs. heterometallic organoaluminum fencholates: Structures and selectivities

  摘要：

  Homo (Al)- and heterometallic (Al, Li)-fencholates and TADDOLates (5-12) yield in methylations of benzaldehyde 1-phenylethanol with up to 90% ee. Surprisingly, the new BISFOL-based (Al, Li)- heterometallic fencholate (11) shows an strong increase and a change of the sense of enantioselectivity from 19% ee (S) to 62% ee (R) in comparison to its (Al)-homometallic fencholate (7). Despite of the presence of nucleophilic methylide groups, the O-BIFOL-based (Al, Li)-heterometallic fencholate (10) yields a stable complex with benzaldehyde, a lithium ion binds the carbonyl group. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.03.013
• 作为产物：
  描述：

  二苯砜 、 (1R)-1,3,3-三甲基二环[2.2.1]庚-2-酮 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 10.0h， 以20%的产率得到biphenyl-2,2'-sulfone-3,3'-bisfenchol
  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