(2S)-2-[(2,5-dimethoxyphenyl)methyl]oxirane | 1097637-56-3

• 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)-2-[(2,5-dimethoxyphenyl)methyl]oxirane
• CAS: 1097637-56-3
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: YRZOAJFPWKSMIS-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(2,5-dimethoxyphenyl)methyl]oxirane 、 5-(tetrahydro-2H-pyran-2-yloxy)pentylmagnesium bromide 在 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以70%的产率得到(2R)-1-(2,5-dimethoxyphenyl)-8-(oxan-2-yloxy)octan-2-ol
  参考文献：
  名称：

  First asymmetric total synthesis of novel and cytotoxic 2′-R-hydroxylanneaquinol

  摘要：

  A novel cytotoxic alkylated hydroquinone 2'-R-hydroxylanneaquinol (1), isolated from the organic extract of the plant Lannea welwitschii, has been synthesized for the first time using commercially available 4-methoxyphenol. The key step of this process involves the kinetic resolution of epoxide 6 using Jacobsen's reaction conditions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.076
• 作为产物：
  描述：

  2-[(2,5-Dimethoxyphenyl)methyl]oxirane 在 (S,S)-(salen)cobalt(III)(OAc) 、 水 作用下， 以47%的产率得到(R)-3-(2,5-dimethoxyphenyl)propane-1,2-diol
  参考文献：
  名称：

  First asymmetric total synthesis of novel and cytotoxic 2′-R-hydroxylanneaquinol

  摘要：

  A novel cytotoxic alkylated hydroquinone 2'-R-hydroxylanneaquinol (1), isolated from the organic extract of the plant Lannea welwitschii, has been synthesized for the first time using commercially available 4-methoxyphenol. The key step of this process involves the kinetic resolution of epoxide 6 using Jacobsen's reaction conditions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.076

文献信息

• First asymmetric total synthesis of novel and cytotoxic 2′-R-hydroxylanneaquinol
  作者：V. Suresh、K. Rajesh、J. Jon Paul Selvam、Y. Venkateswarlu

  DOI：10.1016/j.tetlet.2008.09.076

  日期：2008.12

  A novel cytotoxic alkylated hydroquinone 2'-R-hydroxylanneaquinol (1), isolated from the organic extract of the plant Lannea welwitschii, has been synthesized for the first time using commercially available 4-methoxyphenol. The key step of this process involves the kinetic resolution of epoxide 6 using Jacobsen's reaction conditions. (C) 2008 Elsevier Ltd. All rights reserved.