S-(4-methoxyphenyl) adamantan-1-ylthioate | 1258145-50-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: S-(4-methoxyphenyl) adamantan-1-ylthioate
• 英文别名: S-(4-methoxyphenyl) adamantane-1-carbothioate
• CAS: 1258145-50-4
• 化学式: C₁₈H₂₂O₂S
• 分子量: 302.437
• InChiKey: SJVLZEJMSVQCIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  六氟苯 、 S-(4-methoxyphenyl) adamantan-1-ylthioate 在 hydridotetakis(triphenylphosphine)rhodium(I) 、 1,2-双(二苯基膦)乙烷 作用下， 以 氯苯 为溶剂， 反应 3.0h， 以80%的产率得到1-金刚烷羰基氟化物
  参考文献：
  名称：

  Rhodium-catalyzed interconversion between acid fluorides and thioesters controlled using heteroatom acceptors

  摘要：

  A rhodium complex catalyzed the equilibrium acyl transfer reaction between acid fluorides and thioesters. In the presence of fluoride or thiolate acceptors, the reaction could be shifted to either product. RhH(PPh3)(4)-dppe catalyzed the reaction of acid fluorides and diorgano disulfides in the presence of triphenylphosphine giving thioesters, which was accompanied by triphenylphosphine difluoride. The same complex catalyzed the reaction of aryl thioesters and hexafluorobenzene giving acid fluorides, which was accompanied by 1,4-di(arylthio)-2,3,5,6-tetrafluorobenzenes. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2010.09.009

文献信息

• Equilibrium shift in the rhodium-catalyzed acyl transfer reactions
  作者：Mieko Arisawa、Yui Igarashi、Haruki Kobayashi、Toru Yamada、Kentaro Bando、Takuya Ichikawa、Masahiko Yamaguchi

  DOI：10.1016/j.tet.2011.07.031

  日期：2011.10

  enzene. Acid fluorides were converted into acylphosphine sulfides and thioesters using diphosphine disulfides and disulfides/triphenylphosphine, respectively. Aryl esters were obtained from acid fluorides and phenols in the presence of triphenylsilane. Aryl esters, acylphosphine sulfides, and thioesters were also interconverted in the presence of rhodium complexes. These rhodium-catalyzed acyl transfer

  铑/膦配合物催化酰基氟，芳基酯，酰基膦硫化物和硫代酯之间的平衡酰基转移反应。使用合适的共底物来接受杂原子基团将平衡转移到所需的产物上。使用苯甲酰基五氟苯作为氟化物供体，将酰基膦硫化物和芳基酯转化为酰基氟，并使用（4-甲苯基硫代）五氟苯进行硫酯的氟化反应。分别使用二膦二硫化物和二硫化物/三苯基膦将酰氟转化为酰基膦硫化物和硫酯。在三苯基硅烷的存在下，由酰基氟和苯酚获得芳基酯。在铑配合物的存在下，芳基酯，酰基膦硫化物和硫代酯也可以相互转化。这些铑催化的酰基转移反应在中性条件下进行，无需使用酸或碱。羰基铑中间体参与这些反应是由硫代酯和炔烃的羰基硫化反应提示的。
• Direct transformation of organosulfur compounds to organophosphorus compounds: rhodium-catalyzed synthesis of 1-alkynylphosphine sulfides and acylphosphine sulfides
  作者：Mieko Arisawa、Takuya Watanabe、Masahiko Yamaguchi

  DOI：10.1016/j.tetlet.2011.02.112

  日期：2011.5

  A rhodium-catalyzed method for the synthesis of organophosphorus compounds directly from organosulfur compounds was developed. In the presence of RhH(PPh3)4 and depe, the reaction of 1-alkylthioalkynes with tetraethyldiphosphine disulfide gave 1-alkynylphosphine sulfides. The same complex catalyzed the reaction of thioesters giving acylphosphine sulfides.

  开发了一种铑催化的直接从有机硫化合物合成有机磷化合物的方法。在RhH（PPh 3）4和depe的存在下，1-烷硫基炔烃与四乙基二膦二硫化物的反应得到1-炔基膦硫化物。相同的配合物催化硫代酯的反应，得到酰基膦硫化物。
• Rhodium-catalyzed interconversion between acid fluorides and thioesters controlled using heteroatom acceptors
  作者：Mieko Arisawa、Toru Yamada、Masahiko Yamaguchi

  DOI：10.1016/j.tetlet.2010.09.009

  日期：2010.11

  A rhodium complex catalyzed the equilibrium acyl transfer reaction between acid fluorides and thioesters. In the presence of fluoride or thiolate acceptors, the reaction could be shifted to either product. RhH(PPh3)(4)-dppe catalyzed the reaction of acid fluorides and diorgano disulfides in the presence of triphenylphosphine giving thioesters, which was accompanied by triphenylphosphine difluoride. The same complex catalyzed the reaction of aryl thioesters and hexafluorobenzene giving acid fluorides, which was accompanied by 1,4-di(arylthio)-2,3,5,6-tetrafluorobenzenes. (C) 2010 Published by Elsevier Ltd.