(Z)-2-phenyl-4-(tritylsulfanylmethylene)-5(4H)-oxazolone | 220604-71-7

• 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: (Z)-2-phenyl-4-(tritylsulfanylmethylene)-5(4H)-oxazolone
• 英文别名: 2-phenyl-4-(tritylsulfanylmethylene)-5(4H)-oxazolone；(4Z)-2-phenyl-4-(tritylsulfanylmethylidene)-1,3-oxazol-5-one
• CAS: 220604-71-7
• 化学式: C₂₉H₂₁NO₂S
• 分子量: 447.557
• InChiKey: SXTRKZHJDUGUSA-QLYXXIJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  64
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-2-phenyl-4-(tritylsulfanylmethylene)-5(4H)-oxazolone 在 1,3-二氯-1,1,3,3-四乙基二锡氧烷 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 118.0h， 生成 (+)-menthyl (3R,4S)-3-benzoylamino-4-tritylsulfanyl-4,5-dihydro-3H-pyrazole-3-carboxylate
  参考文献：
  名称：

  Masked constrained cysteines: diastereoselective and enantioselective synthesis of 1-amino-2-mercaptocyclopropanecarboxylic acid derivatives

  摘要：

  A diastereoselective and enantioselective synthesis of (Z)-1-benzovlamino-2-tritylsulfztnvlcvclopropaiiecarboxylic acid derivatives 8a,b and 9a,b was achieved starting from (-)- or (+)-menthyl 2-benzoylamino-3-tritylsulfanylacrylates 3a,b. Compounds 3 were reacted with diazomethane giving the corresponding pyrazolines 4a,b and 5a,b. These compounds. on melting. were transformed, under steric control, into the cyclopropaneamino acid derivatives (R,R)-8a,b and (S,S)-9a,b. The synthesis of a large class of chiral 2-S-alkyl-1-aminocyclopropanecarboxylic acid derivatives is possible after removing the trityl protecting group and subsequent alkylation reactions. (C) 2001 Elsevier Science Ltd. All rights reserved,

  DOI：

  10.1016/s0957-4166(01)00466-9
• 作为产物：
  描述：

  (Z)-2-phenyl-4-(chloromethylene)-5(4H)-oxazolone 、 三苯甲硫醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到(Z)-2-phenyl-4-(tritylsulfanylmethylene)-5(4H)-oxazolone
  参考文献：
  名称：

  一类新型的构象受限的掩蔽半胱氨酸：2-烷基-和2-芳基硫烷基-1-氨基环丙烷羧酸的合成。

  摘要：

  从4-（氯亚甲基）恶唑酮1和硫醇2开始实现了4-硫烷基亚甲基-5（4H）-恶唑酮3的方便合成。恶唑酮3被用作制备未知的2-硫烷基-1-氨基环丙烷羧酸的起始原料导数5和7。恶唑酮3在环外双键处与重氮甲烷环丙烷化，得到具有良好非对映选择性的两种（Z）-和（E）-螺环丙烷恶唑酮4的混合物。然后将它们用乙醇和DMAP处理以产生相应的羧酸盐5。使用碘在乙醇溶液中的溶液，将三苯甲基衍生物5d转化为非对映异构体二硫化物6的混合物。二硫化物6是用于制备3-硫烷基取代的2,3-甲基氨基酸7的便利合成子。

  DOI：

  10.1021/jo9810011

文献信息

• A Novel Class of Conformationally Constrained, Masked Cysteines:  Synthesis of 2-Alkyl- and 2-Arylsulfanyl-1-aminocyclopropanecarboxylic Acids
  作者：F. Clerici、M. L. Gelmi、D. Pocar

  DOI：10.1021/jo9810011

  日期：1999.2.1

  4-(chloromethylene)oxazolone 1 and mercaptans 2. Oxazolones 3 were used as starting materials for the preparation of unknown 2-sulfanyl-1-aminocyclopropanecarboxylic acid derivatives 5 and7. Oxazolones 3 were cyclopropanated at the exocyclic double bond with diazomethane, giving a mixture of the two (Z)- and (E)-spirocyclopropane oxazolones 4 with good diastereoselectivity. These were then treated with

  从4-（氯亚甲基）恶唑酮1和硫醇2开始实现了4-硫烷基亚甲基-5（4H）-恶唑酮3的方便合成。恶唑酮3被用作制备未知的2-硫烷基-1-氨基环丙烷羧酸的起始原料导数5和7。恶唑酮3在环外双键处与重氮甲烷环丙烷化，得到具有良好非对映选择性的两种（Z）-和（E）-螺环丙烷恶唑酮4的混合物。然后将它们用乙醇和DMAP处理以产生相应的羧酸盐5。使用碘在乙醇溶液中的溶液，将三苯甲基衍生物5d转化为非对映异构体二硫化物6的混合物。二硫化物6是用于制备3-硫烷基取代的2,3-甲基氨基酸7的便利合成子。
• Masked constrained cysteines: diastereoselective and enantioselective synthesis of 1-amino-2-mercaptocyclopropanecarboxylic acid derivatives
  作者：Francesca Clerici、Maria Luisa Gelmi、Donato Pocar、Tullio Pilati

  DOI：10.1016/s0957-4166(01)00466-9

  日期：2001.10

  A diastereoselective and enantioselective synthesis of (Z)-1-benzovlamino-2-tritylsulfztnvlcvclopropaiiecarboxylic acid derivatives 8a,b and 9a,b was achieved starting from (-)- or (+)-menthyl 2-benzoylamino-3-tritylsulfanylacrylates 3a,b. Compounds 3 were reacted with diazomethane giving the corresponding pyrazolines 4a,b and 5a,b. These compounds. on melting. were transformed, under steric control, into the cyclopropaneamino acid derivatives (R,R)-8a,b and (S,S)-9a,b. The synthesis of a large class of chiral 2-S-alkyl-1-aminocyclopropanecarboxylic acid derivatives is possible after removing the trityl protecting group and subsequent alkylation reactions. (C) 2001 Elsevier Science Ltd. All rights reserved,