methyl 2-{2-[(benzyloxycarbonylamino)methyl]-4-oxoquinazolin-3(4H)-yl}benzoate | 939966-56-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: methyl 2-{2-[(benzyloxycarbonylamino)methyl]-4-oxoquinazolin-3(4H)-yl}benzoate
• 英文别名: Methyl 2-[4-oxo-2-(phenylmethoxycarbonylaminomethyl)quinazolin-3-yl]benzoate；methyl 2-[4-oxo-2-(phenylmethoxycarbonylaminomethyl)quinazolin-3-yl]benzoate
• CAS: 939966-56-0
• 化学式: C₂₅H₂₁N₃O₅
• 分子量: 443.459
• InChiKey: XFHVSXCRETYPJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  97.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-{2-[(benzyloxycarbonylamino)methyl]-4-oxoquinazolin-3(4H)-yl}benzoate 在 氢溴酸 、 silica gel 、 三乙胺 作用下， 以 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 13.0h， 以65%的产率得到6,7-dihydro-6,8,13a-triaza-benzo[3,4]cyclohepta[1,2-b]naphthalene-5,13-dione
  参考文献：
  名称：

  Hexamethyldisilazane-iodine induced intramolecular dehydrative cyclization of diamides: a general access to natural and unnatural quinazolinones

  摘要：

  A simple and efficient general approach to various quinazolinone scaffolds, including peptidomimetic examples, has been demonstrated by employing HMDS/I-2 for the intramolecular dehydrative cyclization of diamides. The protecting groups -Boc, -Fmoc and -Cbz tolerated the present reaction conditions and we did not observe any racemization. The present protocol has also been used as a key step for the efficient four-step syntheses of the naturally occurring quinazolinones, sclerotigenin, (-)-circumdatin-F and (-)-fumiquinazoline-F. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.032
• 作为产物：
  描述：

  methyl 2-(2-aminobenzoylamino)benzoate 在 碘 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 methyl 2-{2-[(benzyloxycarbonylamino)methyl]-4-oxoquinazolin-3(4H)-yl}benzoate
  参考文献：
  名称：

  Hexamethyldisilazane-iodine induced intramolecular dehydrative cyclization of diamides: a general access to natural and unnatural quinazolinones

  摘要：

  A simple and efficient general approach to various quinazolinone scaffolds, including peptidomimetic examples, has been demonstrated by employing HMDS/I-2 for the intramolecular dehydrative cyclization of diamides. The protecting groups -Boc, -Fmoc and -Cbz tolerated the present reaction conditions and we did not observe any racemization. The present protocol has also been used as a key step for the efficient four-step syntheses of the naturally occurring quinazolinones, sclerotigenin, (-)-circumdatin-F and (-)-fumiquinazoline-F. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.032

文献信息

• Hexamethyldisilazane-iodine induced intramolecular dehydrative cyclization of diamides: a general access to natural and unnatural quinazolinones
  作者：Umesh A. Kshirsagar、Santosh B. Mhaske、Narshinha P. Argade

  DOI：10.1016/j.tetlet.2007.03.032

  日期：2007.4

  A simple and efficient general approach to various quinazolinone scaffolds, including peptidomimetic examples, has been demonstrated by employing HMDS/I-2 for the intramolecular dehydrative cyclization of diamides. The protecting groups -Boc, -Fmoc and -Cbz tolerated the present reaction conditions and we did not observe any racemization. The present protocol has also been used as a key step for the efficient four-step syntheses of the naturally occurring quinazolinones, sclerotigenin, (-)-circumdatin-F and (-)-fumiquinazoline-F. (c) 2007 Elsevier Ltd. All rights reserved.