ethyl N-benzyloxycarbonylanthranilate

• 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: ethyl N-benzyloxycarbonylanthranilate
• 英文别名: ethyl 2-(phenylmethoxycarbonylamino)benzoate
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: YBDAABYHVPALMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.176
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl N-benzyloxycarbonylanthranilate 在 吡啶 、 sodium hydrogen sulfide 、 正丁基锂 、 tetraphosphorus decasulfide 、 硫化氢 、 氢溴酸 、 溶剂黄146 、 碘甲烷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成 sodium;2-aminobenzenecarbodithioate
  参考文献：
  名称：

  Novel Synthesis of 1,2-Dihydro-4H-3,1-benzoxazine-4-thiones by the Reaction of Newsynthesized Methyl Dithioanthranilate Hydrobromide with Carbonyl Compounds and the Formation of Another New Class of 1,2-Dihydro-4H-3,1-benzothiazine-4-thiones from the Same Reactants in the Presence of Excess Sodium Hydrogensulfide

  摘要：

  Methyl dithioanthranilate hydrobromide (6) was synthesized by the deprotection of Z-protected methyl dithioanthranilate (5) which was obtained by treatment of Z-protected methylthioiminium iodide 4 with H2S. The 1,2-dihydro-4H-3,1-benzoxazine-4-thiones 10a-m were first synthesized by the reaction of methyl dithioanthranilate hydrobromide (6) with each aldehyde or ketone. Formaldehyde, in this reaction, gave N-(methylthio)methy1-4H-3,1benzoxazine-4-thione(11). Another new class of 1,2-dihydro-4H-3,1-benzothiazine-4-thiones 12a-e were synthesized from the same reactants in the presence of two equivalents of sodium hydrogensulfide.

  DOI：

  10.3987/com-15-13336
• 作为产物：
  描述：

  氯甲酸苄酯 、 2-氨基苯甲酸乙酯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 以98.6%的产率得到ethyl N-benzyloxycarbonylanthranilate
  参考文献：
  名称：

  Novel Synthesis of 1,2-Dihydro-4H-3,1-benzoxazine-4-thiones by the Reaction of Newsynthesized Methyl Dithioanthranilate Hydrobromide with Carbonyl Compounds and the Formation of Another New Class of 1,2-Dihydro-4H-3,1-benzothiazine-4-thiones from the Same Reactants in the Presence of Excess Sodium Hydrogensulfide

  摘要：

  Methyl dithioanthranilate hydrobromide (6) was synthesized by the deprotection of Z-protected methyl dithioanthranilate (5) which was obtained by treatment of Z-protected methylthioiminium iodide 4 with H2S. The 1,2-dihydro-4H-3,1-benzoxazine-4-thiones 10a-m were first synthesized by the reaction of methyl dithioanthranilate hydrobromide (6) with each aldehyde or ketone. Formaldehyde, in this reaction, gave N-(methylthio)methy1-4H-3,1benzoxazine-4-thione(11). Another new class of 1,2-dihydro-4H-3,1-benzothiazine-4-thiones 12a-e were synthesized from the same reactants in the presence of two equivalents of sodium hydrogensulfide.

  DOI：

  10.3987/com-15-13336

文献信息

• Novel Synthesis of 1,2-Dihydro-4H-3,1-benzoxazine-4-thiones by the Reaction of Newsynthesized Methyl Dithioanthranilate Hydrobromide with Carbonyl Compounds and the Formation of Another New Class of 1,2-Dihydro-4H-3,1-benzothiazine-4-thiones from the Same Reactants in the Presence of Excess Sodium Hydrogensulfide
  作者：Tatsuo Yamamoto、Motomu Muraoka

  DOI：10.3987/com-15-13336

  日期：——

  Methyl dithioanthranilate hydrobromide (6) was synthesized by the deprotection of Z-protected methyl dithioanthranilate (5) which was obtained by treatment of Z-protected methylthioiminium iodide 4 with H2S. The 1,2-dihydro-4H-3,1-benzoxazine-4-thiones 10a-m were first synthesized by the reaction of methyl dithioanthranilate hydrobromide (6) with each aldehyde or ketone. Formaldehyde, in this reaction, gave N-(methylthio)methy1-4H-3,1benzoxazine-4-thione(11). Another new class of 1,2-dihydro-4H-3,1-benzothiazine-4-thiones 12a-e were synthesized from the same reactants in the presence of two equivalents of sodium hydrogensulfide.