(S)-methyl 2-[2-(2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}propanamido)benzamido]benzoate | 939966-40-2

• 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: (S)-methyl 2-[2-(2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}propanamido)benzamido]benzoate
• 英文别名: methyl 2-[[2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoyl]amino]benzoyl]amino]benzoate
• CAS: 939966-40-2
• 化学式: C₃₃H₂₉N₃O₆
• 分子量: 563.61
• InChiKey: XAZYDWUTXYMUID-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-[2-(2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}propanamido)benzamido]benzoate 在 碘 、 六甲基二硅氮烷 作用下， 以 苯 为溶剂， 反应 4.0h， 以75%的产率得到(S)-methyl 2-[2-(1-{[(9H-fluoren-9-yl)methoxy]carbonylamino}ethyl)-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
• 作为产物：
  描述：

  methyl 2-(2-aminobenzoylamino)benzoate 、 N-[(1S)-1-(氯甲酰基)乙基]氨基甲酸芴甲基酯 在 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到(S)-methyl 2-[2-(2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}propanamido)benzamido]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.