(SS)-2-(2'-methoxynaphthylsulfinyl)-1,4-benzoquinone | 259796-82-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (SS)-2-(2'-methoxynaphthylsulfinyl)-1,4-benzoquinone
• CAS: 259796-82-2
• 化学式: C₁₇H₁₂O₄S
• 分子量: 312.346
• InChiKey: QMLOYBIWKTZBGJ-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  三甲硅氧基-2-呋喃 、 (SS)-2-(2'-methoxynaphthylsulfinyl)-1,4-benzoquinone 以 氯仿 为溶剂， 反应 4.0h， 以82%的产率得到(3aR,8bR,SS)-3a,8b-dihydro-7-hydroxy-8-(2'-methoxy-1-naphthylsulfinyl)furo[3,2-b]benzofuran-2(3H)-one
  参考文献：
  名称：

  On the mechanism and diastereoselectivity of 2,3-dihydrobenzofuran formation from sulfinylbenzoquinones and 2-trimethylsilyloxyfuran

  摘要：

  A mechanistic study of the reactions between 2-trimethyisilyloxyfuran 1 and (SS)-2-(arylsulfinyl)- 1,4-benzoquinones 2a and 2b, giving rise to the diastereoselective formation of [3aS,8bS,SS]-3a,8b-dihydro-7-hydroxy-8-(arylsulfinyl)furo[3,2-b]benzofuran-2(3H)-ones 3a and 3b, is reported. The detection and H-1 NMR characterization of several precursors of 3a and 3b accounts for a Michael-type initial reaction which dictates the final diastereoselection of the process. A significant improvement of the stereoselectivity (up to 96% de) in the formation of the tert-butylsulfinyl substituted derivative 3c was achieved by using 2-(tert-butylsulfinyl)- 1,4-benzoquinone 2c as the starting quinone. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00460-7
• 作为产物：
  描述：

  (-)-(1R,2S,5R)-menthyl (S)-2-methoxynaphthalene-1-sulfinate 在 正丁基锂 、 ammonium cerium(IV) nitrate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 (SS)-2-(2'-methoxynaphthylsulfinyl)-1,4-benzoquinone
  参考文献：
  名称：

  On the mechanism and diastereoselectivity of 2,3-dihydrobenzofuran formation from sulfinylbenzoquinones and 2-trimethylsilyloxyfuran

  摘要：

  A mechanistic study of the reactions between 2-trimethyisilyloxyfuran 1 and (SS)-2-(arylsulfinyl)- 1,4-benzoquinones 2a and 2b, giving rise to the diastereoselective formation of [3aS,8bS,SS]-3a,8b-dihydro-7-hydroxy-8-(arylsulfinyl)furo[3,2-b]benzofuran-2(3H)-ones 3a and 3b, is reported. The detection and H-1 NMR characterization of several precursors of 3a and 3b accounts for a Michael-type initial reaction which dictates the final diastereoselection of the process. A significant improvement of the stereoselectivity (up to 96% de) in the formation of the tert-butylsulfinyl substituted derivative 3c was achieved by using 2-(tert-butylsulfinyl)- 1,4-benzoquinone 2c as the starting quinone. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00460-7

文献信息

• Diels−Alder Reactions with 2-(Arylsulfinyl)-1,4-benzoquinones:  Effect of Aryl Substitution on Reactivity, Chemoselectivity, and π-Facial Diastereoselectivity
  作者：M. Carmen Carreño、José L. García Ruano、Antonio Urbano、Cynthia Z. Remor、Yolanda Arroyo

  DOI：10.1021/jo9913107

  日期：2000.1.1

  Eu(fod)(3)- or BF(3).OEt(2)-catalyzed conditions. The synthesis of endo-adduct [4aS,5S,8R,8aR,SS]-9d resulting from cycloaddition on the substituted C(2)-C(3) double bond was achieved in a chemo- and diastereoselective way from quinone 1d in the presence of ZnBr(2). The reactivity and selectivity of the process proved to be dependent on the electron density of the arylsulfinyl group.

  （SS）-2-（2'-甲氧基萘亚磺酰基）-1、4-苯醌（1b），2-（对甲氧基苯基亚磺酰基）-1,4-苯醌（1c）和2-（对-苯基据报道，硝基苯基亚磺酰基）-1,4-苯醌（1d）与环戊二烯。这些环加成反应使非对映异构体内加合物具有高度化学和立体选择性，这是由在热和Eu（fod）（3）-或BF（ 3）.OEt（2）催化的条件。在取代的C（2）-C（3）双键上通过环加成反应制得的内加合物[4aS，5S，8R，8aR，SS] -9d是通过化学和非对映选择性的方式从醌1d中合成的ZnBr（2）的存在。事实证明，该方法的反应性和选择性取决于芳基亚磺酰基的电子密度。