(2S)-3-methyl-2,3-dihydroxy-1-[(2-nitrophenyl)seleno]butane | 247080-03-1

• 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: (2S)-3-methyl-2,3-dihydroxy-1-[(2-nitrophenyl)seleno]butane
• 英文别名: (2S)-3-methyl-1-(2-nitrophenyl)selanylbutane-2,3-diol
• CAS: 247080-03-1
• 化学式: C₁₁H₁₅NO₄Se
• 分子量: 304.204
• InChiKey: OIJISBTVPYVUMF-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.47
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  86.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-3-methyl-2,3-dihydroxy-1-[(2-nitrophenyl)seleno]butane 在 氯化亚砜 、 双氧水 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis of 1,3,2-dioxathiolane-4-methylene-2-oxides: Potential allene oxide equivalents

  摘要：

  Two complementary approaches to 1,3,2-dioxathiolane-4-methylene-2-oxides are described. For example, treatment of 2-hydroxy-2-methylbutan-3-one with thionyl chloride (Et3N, CH2Cl2, -78 degrees C) yields 5,5-dimethyl-1,3,2-dioxathiolane-4-methylene-2-oxide 5 in 58% yield. Alternatively, cyclic sulfite 11, bearing a 4-(2-nitrophenylseleno)methyl substituent. can be induced to undergo oxidative elimination (30% H2O2, THF then CDCl3,Delta) to 5 in 28% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00598-0
• 作为产物：
  描述：

  3-methyl-1-[(2-nitrophenyl)seleno]-2-butene 在 甲基磺酰胺 、 AD-mix-β 作用下， 以 水 、 叔丁醇 为溶剂， 反应 96.0h， 以50%的产率得到(2S)-3-methyl-2,3-dihydroxy-1-[(2-nitrophenyl)seleno]butane
  参考文献：
  名称：

  Synthesis of 1,3,2-dioxathiolane-4-methylene-2-oxides: Potential allene oxide equivalents

  摘要：

  Two complementary approaches to 1,3,2-dioxathiolane-4-methylene-2-oxides are described. For example, treatment of 2-hydroxy-2-methylbutan-3-one with thionyl chloride (Et3N, CH2Cl2, -78 degrees C) yields 5,5-dimethyl-1,3,2-dioxathiolane-4-methylene-2-oxide 5 in 58% yield. Alternatively, cyclic sulfite 11, bearing a 4-(2-nitrophenylseleno)methyl substituent. can be induced to undergo oxidative elimination (30% H2O2, THF then CDCl3,Delta) to 5 in 28% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00598-0

文献信息

• Synthesis of 1,3,2-dioxathiolane-4-methylene-2-oxides: Potential allene oxide equivalents
  作者：Michael Shipman、Heidi R Thorpe、Ian R Clemens

  DOI：10.1016/s0040-4020(99)00598-0

  日期：1999.8

  Two complementary approaches to 1,3,2-dioxathiolane-4-methylene-2-oxides are described. For example, treatment of 2-hydroxy-2-methylbutan-3-one with thionyl chloride (Et3N, CH2Cl2, -78 degrees C) yields 5,5-dimethyl-1,3,2-dioxathiolane-4-methylene-2-oxide 5 in 58% yield. Alternatively, cyclic sulfite 11, bearing a 4-(2-nitrophenylseleno)methyl substituent. can be induced to undergo oxidative elimination (30% H2O2, THF then CDCl3,Delta) to 5 in 28% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.