(2R,3R)-2-((benzyloxy)methyl)-3-((2R,3R)-3-((benzyloxy)methyl)-1-tosylaziridin-2-yl)-1-tosylaziridine | 914982-48-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R)-2-((benzyloxy)methyl)-3-((2R,3R)-3-((benzyloxy)methyl)-1-tosylaziridin-2-yl)-1-tosylaziridine
• 英文别名: (2R,3R)-1-(4-methylphenyl)sulfonyl-2-[(2R,3R)-1-(4-methylphenyl)sulfonyl-3-(phenylmethoxymethyl)aziridin-2-yl]-3-(phenylmethoxymethyl)aziridine
• CAS: 914982-48-2
• 化学式: C₃₄H₃₆N₂O₆S₂
• 分子量: 632.802
• InChiKey: UJQIWNWJTXYGOA-AEEHPLFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-((benzyloxy)methyl)-3-((2R,3R)-3-((benzyloxy)methyl)-1-tosylaziridin-2-yl)-1-tosylaziridine 在 [tetrabutylammonium]2[WSe4] 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以62%的产率得到Cyclic amino diselenide
  参考文献：
  名称：

  Conformationally Locked Bridged Bicyclic Diselenides:  Synthesis, Structure, Se···O Interaction, and Theoretical Studies

  摘要：

  A general synthetic methodology has been developed for the synthesis of a conformationally locked, bridged diselena-bicyclo[3.2.1]octane skeleton by regio- and stereospecific tandem nucleophilic ring opening of cis-1,4-aziridino-epoxides with tetraethylammonium tetraselenotungstate [Et4N](2)WSe4, 1, in a one-pot synthesis. Some correlations have been made on the physicochemical characteristics of the diselenides with a change in the dihedral angles.

  DOI：

  10.1021/jo070705k
• 作为产物：
  描述：

  甘露醇 在 Lindlar's catalyst 吡啶 、 三乙基硅烷 、 sodium azide 、 硫酸 、 三氟化硼乙醚 、 氢气 、 三氯化铁 、 sodium hydride 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 110.0 ℃ 、101.33 kPa 条件下， 反应 180.5h， 生成 (2R,3R)-2-((benzyloxy)methyl)-3-((2R,3R)-3-((benzyloxy)methyl)-1-tosylaziridin-2-yl)-1-tosylaziridine
  参考文献：
  名称：

  Synthesis of enantiopure bis-aziridines, bis-epoxides, and aziridino-epoxides from d-mannitol

  摘要：

  A practical synthesis of enantiopure bis-aziridines 11 and 15, bis-epoxides 12 and 17, and aziridino-epoxides 27 and 30 is reported using inexpensive D-mannitol as the starting material. The key transformation involves the reductive cleavage of bis-benzylidene acetal 3 to form dimesylate 4, which was further converted to monoazides and diazides followed by reduction, mesylation, and cyclization to furnish the required compounds in good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.08.035

文献信息

• Synthesis of enantiopure bis-aziridines, bis-epoxides, and aziridino-epoxides from d-mannitol
  作者：Devarajulu Sureshkumar、Susama Maity、Srinivasan Chandrasekaran

  DOI：10.1016/j.tet.2006.08.035

  日期：2006.10

  A practical synthesis of enantiopure bis-aziridines 11 and 15, bis-epoxides 12 and 17, and aziridino-epoxides 27 and 30 is reported using inexpensive D-mannitol as the starting material. The key transformation involves the reductive cleavage of bis-benzylidene acetal 3 to form dimesylate 4, which was further converted to monoazides and diazides followed by reduction, mesylation, and cyclization to furnish the required compounds in good yields. (c) 2006 Elsevier Ltd. All rights reserved.
• Conformationally Locked Bridged Bicyclic Diselenides:  Synthesis, Structure, Se···O Interaction, and Theoretical Studies
  作者：Devarajulu Sureshkumar、Venkataraman Ganesh、Srinivasan Chandrasekaran

  DOI：10.1021/jo070705k

  日期：2007.7.1

  A general synthetic methodology has been developed for the synthesis of a conformationally locked, bridged diselena-bicyclo[3.2.1]octane skeleton by regio- and stereospecific tandem nucleophilic ring opening of cis-1,4-aziridino-epoxides with tetraethylammonium tetraselenotungstate [Et4N](2)WSe4, 1, in a one-pot synthesis. Some correlations have been made on the physicochemical characteristics of the diselenides with a change in the dihedral angles.