(E)-5-diphenylphosphinoyl-4-methyldec-2-en-4-ol | 96302-65-7

• 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)-5-diphenylphosphinoyl-4-methyldec-2-en-4-ol
• 英文别名: (E)-5-diphenylphosphoryl-4-methyldec-2-en-4-ol
• CAS: 96302-65-7；98753-94-7；98753-95-8
• 化学式: C₂₃H₃₁O₂P
• 分子量: 370.472
• InChiKey: IDMPRLRSEWYQPX-PTXOJBNSSA-N

物化性质

• 沸点：
  483.6±38.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-5-diphenylphosphinoyl-4-methyldec-2-en-4-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以60%的产率得到(E)-5-diphenylphosphinoyl-4-methyldec-3-en-2-one
  参考文献：
  名称：

  The synthesis of (Z)-penta-2,4-dien-1-ol and substituted (E)-pentadienols by the stereochemically controlled Horner–Wittig reaction

  摘要：

  Acylation of Ph2P(O)Me with a lactone gives a Horner-Wittig intermediate with a Z-double bond protected as a Diels-Alder adduct with furan and hence (Z)-penta-2,4-dien-1-ol. Substituted (E)-penta-2,4-dien-1-ols are available by a more general route involving addition of enals to phosphine oxides, a regiochemically controlled allylic alcohol transposition, and a Horner-Wittig reaction. The geometry of only one double bond can be controlled.

  DOI：

  10.1039/p19910001485
• 作为产物：
  描述：

  3-戊烯-2-酮 、 heptyl(diphenyl)phosphineoxide 在 正丁基锂 作用下， 生成 (E)-5-diphenylphosphinoyl-4-methyldec-2-en-4-ol
  参考文献：
  名称：

  The synthesis of (Z)-penta-2,4-dien-1-ol and substituted (E)-pentadienols by the stereochemically controlled Horner–Wittig reaction

  摘要：

  Acylation of Ph2P(O)Me with a lactone gives a Horner-Wittig intermediate with a Z-double bond protected as a Diels-Alder adduct with furan and hence (Z)-penta-2,4-dien-1-ol. Substituted (E)-penta-2,4-dien-1-ols are available by a more general route involving addition of enals to phosphine oxides, a regiochemically controlled allylic alcohol transposition, and a Horner-Wittig reaction. The geometry of only one double bond can be controlled.

  DOI：

  10.1039/p19910001485

文献信息

• Stereochemical control (E/Z and syn/anti) by the diphenylphosphinoyl group in the synthesis of allylic alcohols by allylic rearrangement and by 1,4-diastereoselective reduction of enones
  作者：Jonathan Clayden、Eric W. Collington、Jason Elliott、Stephen J. Martin、Andrew B. McElroy、Stuart Warren、David Waterson

  DOI：10.1039/p19930001849

  日期：——

  Allylic rearrangement of substitued 2-hydroxyalk-3-en-1-yl(diphenyl)phosphine oxides to 4-hydroxyalk-2-en-1-yl(diphenyl)phosphine oxides can be performed with total regio- and reasonable stereochemical control. Alternatively, the reduction of substituted 4-diphenylphosphinoylbut-2-en-1 -ones shows remarkable 1,4-diastereoselectivity. All these reactions are directed by the diphenylphosphinoyl (Ph2PO)

  取代的2-羟基烷-3-烯-1-基（二苯基）膦氧化物的烯丙基重排为4-羟基烷-2-烯-1-基（二苯基）膦氧化物可以在完全区域和合理的立体化学控制下进行。或者，取代的4-二苯基膦酰基丁-2-烯-1-酮的还原显示出显着的1，4-非对映选择性。所有这些反应均由二苯基膦酰基（Ph 2 PO）基团指导。
• Transposition of allylic alcohols controlled by the Ph2PO group: Reagents for α-hydroxy-diene synthesis by the horner-wittig reaction
  作者：Paul S. Brown、Andrew B. McElroy、Stuart Warren

  DOI：10.1016/s0040-4039(00)61892-0

  日期：1985.1

  4-Hydroxy-2-alkenyldiphenylphosphine oxides, prepared by a phosphorus-controlled allylic rearrangement, give dianions and hence α-hydroxydienes (substituted penta-2,4-dienols) by the Horner-Wittig reaction.

  通过磷控制的烯丙基重排制备的4-羟基-2-烯基二苯基氧化膦通过霍纳-维蒂希反应产生二价阴离子，因此产生α-羟基二烯（取代的5,2,4-二烯酚）。
• Stereocontrolled synthesis of δ-hydroxy allylic phosphine oxides by allylic ester transposition
  作者：Andrew B. McElroy、Stuart Warren

  DOI：10.1016/s0040-4039(00)98583-6

  日期：1985.1
• MCELROY, A. B.;WARREN, S., TETRAHEDRON LETT., 1985, 26, N 13, 1677-1680
  作者：MCELROY, A. B.、WARREN, S.

  DOI：——

  日期：——
• BROWN, P. S.;MCELROY, A. B.;WARREN, S., TETRAHEDRON LETT., 1985, 26, N 2, 249-252
  作者：BROWN, P. S.、MCELROY, A. B.、WARREN, S.

  DOI：——

  日期：——