N-[(2R,5S)-2-(2,2-dimethoxyethyl)-1,3-dioxacycloheptan-5-yl]benzoylamine | 296766-52-4

• 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: N-[(2R,5S)-2-(2,2-dimethoxyethyl)-1,3-dioxacycloheptan-5-yl]benzoylamine
• 英文别名: [(2R,5S)-N-2-(2,2-dimethoxyethyl)-1,3-dioxacycloheptan-5-yl]benzamide；N-[(2R,5S)-2-(2,2-dimethoxyethyl)-1,3-dioxepan-5-yl]benzamide
• CAS: 296766-52-4
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: ZQTWSIXOOGEIDF-DZGCQCFKSA-N

物化性质

• 熔点：
  85-87 °C
• 沸点：
  473.4±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(2R,5S)-2-(2,2-dimethoxyethyl)-1,3-dioxacycloheptan-5-yl]benzoylamine 在 草酸 、 silica gel 作用下， 以 氯仿 为溶剂， 生成 (2R,5S)-N-(2-formylmethyl-1,3-dioxacycloheptane-5-yl)benzamide
  参考文献：
  名称：

  Diasteroselective Cyclizations with Enantiopure Malonaldehyde Monocycloacetals

  摘要：

  The synthesis of a series of enantiopure malonaldehyde monocycloacetals is described. Treatment of 8b with L-tryptophan methyl ester, 5-methoxytryptamine, and tryptamine, respectively, in the Pictet-Spengler condensation gave the corresponding enantiomerically pure key precursors 1-3 and 17-21 in only two steps. Using a chiral amino-diol successfully realized the kinetic resolution of racemic carbolines 23 and 24.

  DOI：

  10.1021/jo0057351
• 作为产物：
  描述：

  1,1,3,3-四甲氧基丙烷 在 三甲基氯硅烷 、 三乙胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 N-[(2R,5S)-2-(2,2-dimethoxyethyl)-1,3-dioxacycloheptan-5-yl]benzoylamine
  参考文献：
  名称：

  Stereoselective synthesis and anti-inflammatory activities of 6- and 7-membered dioxacycloalkanes

  摘要：

  A class of 5-trifluoroacetylamino-1,3-dioxacycloalkanes, 5-benzoylamino-1,3-dioxacycloalkanes and 5-amino-1,3-dioxacycloalkane compounds were stereoselectively synthesized as potential anti-inflammatory drug candidates. The anti -inflammatory activities of these compounds were tested using the xylene-induced mouse ear edema model, from which multiple compounds possessing anti-inflammatory properties which surpass aspirin were identified; these compounds were then compared to establish structure-activity relationships. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.068

文献信息

• Stereoselective Transacetalization of 1,1,3,3-Tetramethoxypropane andN-Benzoylaminodiols
  作者：Lanrong Bi、Ming Zhao、Chao Wang、Shiqi Peng

  DOI：10.1002/1099-0690(200007)2000:14<2669::aid-ejoc2669>3.3.co;2-q

  日期：2000.7
• Stereoselective synthesis and anti-inflammatory activities of 6- and 7-membered dioxacycloalkanes
  作者：Keli Gu、Lanrong Bi、Ming Zhao、Chao Wang、Cheryl Dolan、Michael C. Kao、Jeffrey B.-H. Tok、Shiqi Peng

  DOI：10.1016/j.bmc.2005.09.068

  日期：2006.3

  A class of 5-trifluoroacetylamino-1,3-dioxacycloalkanes, 5-benzoylamino-1,3-dioxacycloalkanes and 5-amino-1,3-dioxacycloalkane compounds were stereoselectively synthesized as potential anti-inflammatory drug candidates. The anti -inflammatory activities of these compounds were tested using the xylene-induced mouse ear edema model, from which multiple compounds possessing anti-inflammatory properties which surpass aspirin were identified; these compounds were then compared to establish structure-activity relationships. (c) 2005 Elsevier Ltd. All rights reserved.
• Diasteroselective Cyclizations with Enantiopure Malonaldehyde Monocycloacetals
  作者：Lanrong Bi、Ming Zhao、Chao Wang、Shiqi Peng、Ekkehard Winterfeldt

  DOI：10.1021/jo0057351

  日期：2002.1.1

  The synthesis of a series of enantiopure malonaldehyde monocycloacetals is described. Treatment of 8b with L-tryptophan methyl ester, 5-methoxytryptamine, and tryptamine, respectively, in the Pictet-Spengler condensation gave the corresponding enantiomerically pure key precursors 1-3 and 17-21 in only two steps. Using a chiral amino-diol successfully realized the kinetic resolution of racemic carbolines 23 and 24.