(1-methyl-1-nitro-ethyl)-oxirane | 20030-57-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (1-methyl-1-nitro-ethyl)-oxirane
• 英文别名: 2-(2-Nitropropan-2-yl)oxirane；2-(2-nitropropan-2-yl)oxirane
• CAS: 20030-57-3
• 化学式: C₅H₉NO₃
• 分子量: 131.131
• InChiKey: BXXLVYDUPRONMM-UHFFFAOYSA-N

物化性质

• 沸点：
  204.5±13.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1-methyl-1-nitro-ethyl)-oxirane 在 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 5-[(Dimethylamino)methyl]-4,4-dimethyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Novel 3-chlorooxazolidin-2-ones as antimicrobial agents

  摘要：

  Antimicrobial resistance against many known therapeutics is on the rise. We examined derivatives of 3-chlorooxazolidin-2-one 1a (X = H) as antibacterial and antifungal agents. The key findings were that the activity and apparent in vitro cytotoxicity could be controlled by the substitution of charged solubilizers at the 4- and 5-positions. These changes both significantly increase the antifungal potency and decrease cytotoxicity. Particularly effective were trialkylammonium groups which led to 400- to 600-fold increases in the antifungal therapeutic index when compared to their unsubstituted counterparts. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.036
• 作为产物：
  描述：

  3-methyl-3-nitro-1-butene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到(1-methyl-1-nitro-ethyl)-oxirane
  参考文献：
  名称：

  Novel 3-chlorooxazolidin-2-ones as antimicrobial agents

  摘要：

  Antimicrobial resistance against many known therapeutics is on the rise. We examined derivatives of 3-chlorooxazolidin-2-one 1a (X = H) as antibacterial and antifungal agents. The key findings were that the activity and apparent in vitro cytotoxicity could be controlled by the substitution of charged solubilizers at the 4- and 5-positions. These changes both significantly increase the antifungal potency and decrease cytotoxicity. Particularly effective were trialkylammonium groups which led to 400- to 600-fold increases in the antifungal therapeutic index when compared to their unsubstituted counterparts. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.036

文献信息

• Novel 3-chlorooxazolidin-2-ones as antimicrobial agents
  作者：Timothy P. Shiau、Eric D. Turtle、Charles Francavilla、Nichole J. Alvarez、Meghan Zuck、Lisa Friedman、Donogh J.R. O’Mahony、Eddy Low、Mark B. Anderson、Ramin (Ron) Najafi、Rakesh K. Jain

  DOI：10.1016/j.bmcl.2011.03.036

  日期：2011.5

  Antimicrobial resistance against many known therapeutics is on the rise. We examined derivatives of 3-chlorooxazolidin-2-one 1a (X = H) as antibacterial and antifungal agents. The key findings were that the activity and apparent in vitro cytotoxicity could be controlled by the substitution of charged solubilizers at the 4- and 5-positions. These changes both significantly increase the antifungal potency and decrease cytotoxicity. Particularly effective were trialkylammonium groups which led to 400- to 600-fold increases in the antifungal therapeutic index when compared to their unsubstituted counterparts. (C) 2011 Elsevier Ltd. All rights reserved.