1-(2E,2-methylbutenyl)triethylphosphonium bromide | 1234209-12-1

• 分子结构分类: 有机化合物 - 有机磷化合物 - 四烷基鏻化合物
• 英文名称: 1-(2E,2-methylbutenyl)triethylphosphonium bromide
• 英文别名: triethyl-[(E)-2-methylbut-2-enyl]phosphanium;bromide
• CAS: 1234209-12-1
• 化学式: Br*C₁₁H₂₄P
• 分子量: 267.189
• InChiKey: SBQMLBDPXGMOHL-ICSBZGNSSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.03
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+)-香茅醛 、 1-(2E,2-methylbutenyl)triethylphosphonium bromide 在 lithium chloride 、 lithium hydroxide 作用下， 以 水 为溶剂， 反应 3.03h， 生成 (2Z,4E)(R)-(+)-caparratriene 、 (2E,4E)(R)-(+)-caparratriene
  参考文献：
  名称：

  A short synthesis of the anti-leukemic sesquiterpene (+)-caparratriene employing aqueous Wittig chemistry

  摘要：

  An efficient, stereoselective method for the synthesis of (+)-caparratriene based on an aqueous Wittig reaction has been developed. A functionalized triethylallyl ylide reacted under various conditions with (+)-citronellal to deliver (+)-caparratriene in only three steps with excellent overall yield. The Wittig reaction proceeded with exclusive (4E)-selectivity and an interesting cationic effect was uncovered with good stereoselectivity at the isomerizable allylic position being observed in the presence of lithium salts. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.035
• 作为产物：
  描述：

  triethylphosphine hydrobromide 、 (E)-2-methyl-2-buten-1-ol 反应 0.17h， 以99%的产率得到1-(2E,2-methylbutenyl)triethylphosphonium bromide
  参考文献：
  名称：

  A short synthesis of the anti-leukemic sesquiterpene (+)-caparratriene employing aqueous Wittig chemistry

  摘要：

  An efficient, stereoselective method for the synthesis of (+)-caparratriene based on an aqueous Wittig reaction has been developed. A functionalized triethylallyl ylide reacted under various conditions with (+)-citronellal to deliver (+)-caparratriene in only three steps with excellent overall yield. The Wittig reaction proceeded with exclusive (4E)-selectivity and an interesting cationic effect was uncovered with good stereoselectivity at the isomerizable allylic position being observed in the presence of lithium salts. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.035

文献信息

• A short synthesis of the anti-leukemic sesquiterpene (+)-caparratriene employing aqueous Wittig chemistry
  作者：Priyabrata Das、James McNulty

  DOI：10.1016/j.tetlet.2010.04.035

  日期：2010.6

  An efficient, stereoselective method for the synthesis of (+)-caparratriene based on an aqueous Wittig reaction has been developed. A functionalized triethylallyl ylide reacted under various conditions with (+)-citronellal to deliver (+)-caparratriene in only three steps with excellent overall yield. The Wittig reaction proceeded with exclusive (4E)-selectivity and an interesting cationic effect was uncovered with good stereoselectivity at the isomerizable allylic position being observed in the presence of lithium salts. (C) 2010 Elsevier Ltd. All rights reserved.