(E)-3-[(2R,3R)-3-(4-Chloro-phenyl)-oxiranyl]-prop-2-en-1-ol | 136590-85-7

• 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: (E)-3-[(2R,3R)-3-(4-Chloro-phenyl)-oxiranyl]-prop-2-en-1-ol
• 英文别名: (E)-3-[(2R,3R)-3-(4-chlorophenyl)oxiran-2-yl]prop-2-en-1-ol
• CAS: 136590-85-7
• 化学式: C₁₁H₁₁ClO₂
• 分子量: 210.66
• InChiKey: FQCGKOXGJFHQKA-COUIAZAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  32.76
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 、 4-hydroxy-2E-butenyl-triphenylarsonium 在 potassium fluoride on basic alumina 作用下， 以 水 、 乙腈 为溶剂， 反应 20.0h， 以66%的产率得到(E)-3-[(2R,3R)-3-(4-Chloro-phenyl)-oxiranyl]-prop-2-en-1-ol
  参考文献：
  名称：

  Highly stereoselective one-step synthesis of 5-aryl- and 5-(2-styrenyl)-4,5-trans-epoxy-2(E)-pentenols employing an arsonium salt

  摘要：

  5-Aryl- and 5-(2-styrenyl)-4,5-trans-epoxy-2E-penten-l-ols were conveniently synthesized by a one-step reaction of aldehydes with arsonium salt 2b under mild conditions (rt, KF.Al2O3, phase transfer).

  DOI：

  10.1016/0040-4039(91)80610-i

文献信息

• Synthesis of 2-(α-Substituted N-Tosylaminomethyl)-2,5-Dihydrofurans by Reaction of N-Sulfonylimines with Arsonium or Sulfonium 4-Hydroxyl-cis-2-butenylides
  作者：Wei-Ping Deng、An-Hu Li、Li-Xin Dai、Xue-Long Hou

  DOI：10.1016/s0040-4020(00)00191-5

  日期：2000.5

  On treatment of N-tosylimines 1 and 4-hydroxyl-cis-butenyl arsonium salt 5 or sulfonium salt 11a with KOH in acetonitrile at room temperature, 2-(alpha-substituted N-tosylaminomethyl)-2,5-dihydrofurans 4 were obtained in moderate yields through a new ylide cyclization process. Ylide 2 acts formally as an equivalent of the 2,5-dihydrofuran anion. However, the reaction of 4-hydroxyl-trans-butenyl sulfonium salt 11b with N-tosylimine 1b under the same conditions gave only the normal aziridinadon product 12. A plausible mechanism was proposed for this new 5-membered cyclization reaction, and a high yield process for the synthesis of target molecules 4 is also recommended. (C) 2000 Elsevier Science Ltd. All rights reserved.