dimethyl 4-isothiocyanatoisophthalate | 342803-20-7

• 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: dimethyl 4-isothiocyanatoisophthalate
• 英文别名: Dimethyl 4-isothiocyanatobenzene-1,3-dicarboxylate
• CAS: 342803-20-7
• 化学式: C₁₁H₉NO₄S
• 分子量: 251.263
• InChiKey: YCBXSRZDFIUJSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  97
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 4-isothiocyanatoisophthalate 、 3,4-二氨基苯甲酸甲酯 在 达卡巴嗪 、 barium hydroxide octahydrate 作用下， 以 二氯甲烷 、 1,4-二氧六环 为溶剂， 反应 16.43h， 生成 dimethyl 12(5H)-oxobenzimidazo[2,1-b]quinazoline-2,9-dicarboxylate
  参考文献：
  名称：

  Microwave-Mediated Heterocyclization to Benzimidazo[2,1-b]quinazolin-12(5H)-ones

  摘要：

  An effective route to benzimidazo[2,1-b]quinazolin-12(5H)-ones from commercially available o-aryl isothiocyanate esters and o-phenylenediamines is reported. This method accommodates a variety of substituents on either starting material and proceeds under microwave irradiation in the presence of barium hydroxide, conditions that do not hydrolyze methyl ester substituents. The pharmacologically pertinent benzimidazoquinazolinone heterocycle is delivered in excellent yield and purity via both solution- and solid-phase protocols, the latter involving traceless release from the resin.

  DOI：

  10.1021/jo0618066
• 作为产物：
  描述：

  硫光气 、 4-氨基异邻苯二甲酸二甲酯 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以90%的产率得到dimethyl 4-isothiocyanatoisophthalate
  参考文献：
  名称：

  Microwave-Mediated Heterocyclization to Benzimidazo[2,1-b]quinazolin-12(5H)-ones

  摘要：

  An effective route to benzimidazo[2,1-b]quinazolin-12(5H)-ones from commercially available o-aryl isothiocyanate esters and o-phenylenediamines is reported. This method accommodates a variety of substituents on either starting material and proceeds under microwave irradiation in the presence of barium hydroxide, conditions that do not hydrolyze methyl ester substituents. The pharmacologically pertinent benzimidazoquinazolinone heterocycle is delivered in excellent yield and purity via both solution- and solid-phase protocols, the latter involving traceless release from the resin.

  DOI：

  10.1021/jo0618066

文献信息

• KIENZLE, F.;KAISER, A.;MINDER, R. E., HELV. CHIM. ACTA, 1983, 66, N 1, 148-157
  作者：KIENZLE, F.、KAISER, A.、MINDER, R. E.

  DOI：——

  日期：——
• KABBE H.-J., J. LIEBIGS ANN. CHEM., 1978, NO 3, 398-404
  作者：KABBE H.-J.

  DOI：——

  日期：——
• Microwave-Mediated Heterocyclization to Benzimidazo[2,1-<i>b</i>]quinazolin-12(5<i>H</i>)-ones
  作者：Richard D. Carpenter、Kit S. Lam、Mark J. Kurth

  DOI：10.1021/jo0618066

  日期：2007.1.1

  An effective route to benzimidazo[2,1-b]quinazolin-12(5H)-ones from commercially available o-aryl isothiocyanate esters and o-phenylenediamines is reported. This method accommodates a variety of substituents on either starting material and proceeds under microwave irradiation in the presence of barium hydroxide, conditions that do not hydrolyze methyl ester substituents. The pharmacologically pertinent benzimidazoquinazolinone heterocycle is delivered in excellent yield and purity via both solution- and solid-phase protocols, the latter involving traceless release from the resin.