2-Naphthyl 2-pyridyl disulfide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Naphthyl 2-pyridyl disulfide
• 英文别名: 2-(Naphthalen-2-yldisulfanyl)pyridine；2-(naphthalen-2-yldisulfanyl)pyridine
• 化学式: C₁₅H₁₁NS₂
• 分子量: 269.391
• InChiKey: USWCSGXLOYGWBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Naphthyl 2-pyridyl disulfide 、 3^A,6^A-anhydro-2^A-deoxy-2^A-thio-β-cyclodextrin 以51%的产率得到
  参考文献：
  名称：

  2A,3A-Alloepithio-2A,3A-dideoxy-β-cyclodextrin: synthesis and application in the construction of rigid elliptical cavities with functionality at the secondary hydroxyl side

  摘要：

  2(A),3(A)-Alloepithio-2(A),3(A)-dideoxy-beta-cyclodextrin (2), which may serve as a novel and important interniediate for the functionalization of the secondary face of beta-cyclodextrin, was prepared in 40% yield by heating 2(A),3(A)-mannoepoxy-beta-cyclodextrin and thiourea in water. Treatment of 2 with AgNO3 in the presence of amines afforded 3(A),6(A)-anhydro-2(A)-deoxy-2(A)-thio-beta-cyclodextrin (4) in 73% yield. The latter is an artificial enzyme candidate with a specifically orientated thiol group and a rigid elliplical cavity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.031
• 作为产物：
  描述：

  在 2-萘硫醇 作用下， 以 氘代苯 为溶剂， 反应 0.08h， 生成 2-Naphthyl 2-pyridyl disulfide 、 (2S*,5S*)-2-isopropyl-5-phenyltetrahydrofuran 、 (2S*,5R*)-2-isopropyl-5-phenyltetrahydrofuran
  参考文献：
  名称：

  Hartung, Jens; Hiller, Margit; Schmidt, Philipp, Liebigs Annalen, 1996, # 9, p. 1425 - 1436

  摘要：

  DOI：

文献信息

• Ring Closure Reactions of Substituted 4-Pentenyl-1-oxy Radicals. The Stereoselective Synthesis of Functionalized Disubstituted Tetrahydrofurans
  作者：Jens Hartung、Fabienne Gallou

  DOI：10.1021/jo00126a021

  日期：1995.10

  N-(Alkyloxy)pyridine-2( VT)-thiones 3 and benzenesulfenic acid O-esters 5 have been synthesized from substituted 4-pentenols 1 or the derived tosylates. Compounds 3 and 5 are efficient sources of free alkoxy radicals 6 which undergo synthetically useful fast ring closure reactions 6 --> 8 [k(exo) = (2 +/- 1) x 10(8) s(-1) to (6 +/- 2) x 10(9) s(-1) (T = 30 +/- 0.2 degrees C)]. Tetrahydrofurfuryl radicals 8 can be trapped with, e.g., hydrogen or chlorine atom donors to afford either trans- or cis-disubstituted tetrahydrofurans 10 or 12 depending on the substitution pattern of the 4-pentenyloxy radical. Substituted tetrahydropyrans 11 or 13 are formed in the minor 6-endo-trig cyclization. According to the data of competition kinetics, the observed stereoselectivities in free alkoxy radical cyclizations arise from steric interactions between the substituents in the transition state of the ring closure reactions. Alkyl substituents cause small differences in the measured relative rate constants of B-exo cyclizations which are reminiscent of the data obtained from the rearrangements of alkyl-substituted 5-hexenyl radicals. Likewise, a stereochemical model for oxygen radical cyclization is proposed where the pentenyloxy chain adopts a six-membered, chairlike transition state with the alkyl substituents preferentially situated in the pseudoequatorial positions leading to 2,5-trans-, 2,4-cis-, and 2,3-trans-substituted tetrahydrofurfuryl radicals 8 as the major intermediates.