(+/-)-1,3-diacetyl-4,5-diphenyl-2-imidazolidinethione | 137618-04-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (+/-)-1,3-diacetyl-4,5-diphenyl-2-imidazolidinethione
• 英文别名: 1,3-diacetyl-trans-4,5-diphenylimidazolidine-2-thione；1-[(4S,5S)-3-acetyl-4,5-diphenyl-2-sulfanylideneimidazolidin-1-yl]ethanone
• CAS: 137618-04-3；139122-10-4
• 化学式: C₁₉H₁₈N₂O₂S
• 分子量: 338.43
• InChiKey: XKDCHJOKVGGULV-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  72.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-1,3-diacetyl-4,5-diphenyl-2-imidazolidinethione 在 mercury(II) diacetate 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到(+/-)-1,3-diacetyl-4,5-diphenylimidazolidinethione
  参考文献：
  名称：

  Bifunctional chiral auxiliaries 2: the synthesis of 1,3-diacylimidazolidin-2-ones from 1,2-diamines

  摘要：

  The title compounds are readily prepared in three steps via the corresponding 1,3-diacylimidazolidine-2-thiones. The final step involves the novel use of mercury (II) acetate for the conversion of thioureas to ureas.

  DOI：

  10.1016/s0040-4039(00)92309-8
• 作为产物：
  描述：

  1,2-二苯基乙烷-1,2-二胺 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 31.0h， 生成 (+/-)-1,3-diacetyl-4,5-diphenyl-2-imidazolidinethione
  参考文献：
  名称：

  Bifunctional chiral auxiliaries 5: The synthesis of 1,3-diacylimidazolidine-2-thiones and 1,3-diacylimidazolidin-2-ones from 1,2-diamines

  摘要：

  Although 1,2-diamines fail to cyclise with urea, phosgene or 1,1'-carbonyl diimidazole, they react with carbon disulphide to give the corresponding imidazolidine-2-thiones. These undergo clean diacylation to give 1,3-diacylimidazolidine-2-thiones which are readily converted to 1,3-diacylimidazolidin-2-ones on treatment with mercury (II) acetate. An alternative two-step route to 1,3-diacylimidazolidin-2-ones uses carbonyl sulphide to effect cyclisation of the 1,2-diamine to the imidazolidin-2-one, which is subsequently diacylated. The ability to convert homochiral 1,2-diamines to homochiral 1,3-diacylimidazolidin-2-ones has also been demonstrated.

  DOI：

  10.1016/s0040-4020(01)85757-4

文献信息

• The efficient enantiodivergence of (dl)-1,3-diacetyl-2-imidazolidinethiones by enantioselective catalytic deacetylation
  作者：Kazuhiro Yokoyama、Tadao Ishizuka、Takehisa Kunieda

  DOI：10.1016/s0040-4039(99)01277-0

  日期：1999.8

  An enantioselective borane-mediated deacylation of C2 - symmetrical 1,3-diacetyl-2-imidazolidinethiones, catalyzed by oxazaborolidines derived in situ from an aminoalcohol 2 and borane, provides a promising process for highly effective kinetic resolution.

  由氨基醇2和硼烷原位衍生的恶唑硼烷催化的对映选择性硼烷介导的C 2对称1,3-二乙酰基-2-咪唑烷硫酮的对乙酰化脱酰基为有效的动力学拆分提供了有希望的方法。
• Bifunctional chiral auxiliaries 2: the synthesis of 1,3-diacylimidazolidin-2-ones from 1,2-diamines
  作者：Stephen G. Davies、Andrew A. Mortlock

  DOI：10.1016/s0040-4039(00)92309-8

  日期：1991.1

  The title compounds are readily prepared in three steps via the corresponding 1,3-diacylimidazolidine-2-thiones. The final step involves the novel use of mercury (II) acetate for the conversion of thioureas to ureas.
• Bifunctional chiral auxiliaries 5: The synthesis of 1,3-diacylimidazolidine-2-thiones and 1,3-diacylimidazolidin-2-ones from 1,2-diamines
  作者：Stephen G. Davies、Andrew A. Mortlock

  DOI：10.1016/s0040-4020(01)85757-4

  日期：1993.1

  Although 1,2-diamines fail to cyclise with urea, phosgene or 1,1'-carbonyl diimidazole, they react with carbon disulphide to give the corresponding imidazolidine-2-thiones. These undergo clean diacylation to give 1,3-diacylimidazolidine-2-thiones which are readily converted to 1,3-diacylimidazolidin-2-ones on treatment with mercury (II) acetate. An alternative two-step route to 1,3-diacylimidazolidin-2-ones uses carbonyl sulphide to effect cyclisation of the 1,2-diamine to the imidazolidin-2-one, which is subsequently diacylated. The ability to convert homochiral 1,2-diamines to homochiral 1,3-diacylimidazolidin-2-ones has also been demonstrated.