(2RS,3SR,4SR)-2,4-diphenyl-5-hexen-3-ol | 104047-04-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (2RS,3SR,4SR)-2,4-diphenyl-5-hexen-3-ol
• 英文别名: (2S,3R,4R)-2,4-diphenylhex-5-en-3-ol
• CAS: 104047-04-3；104111-44-6；104111-45-7；104111-46-8；124096-18-0；124096-19-1；124096-20-4；124149-99-1
• 化学式: C₁₈H₂₀O
• 分子量: 252.356
• InChiKey: NYUPQEHEIONODT-BMGDILEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2RS,3SR,4SR)-2,4-diphenyl-5-hexen-3-ol 生成 [(2S,3R,4R)-2,4-diphenylhex-5-en-3-yl] 3,5-dinitrobenzoate
  参考文献：
  名称：

  COXON, JAMES M.;VAN, BYK STEPHEN J.;STEEL, PETER J., TETRAHEDRON, 45,(1989) N, C. 1029-1041

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酸桂酯 、 (R)-2-phenylpropanal 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 联硼酸频那醇酯 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 以58%的产率得到(2RS,3SR,4SR)-2,4-diphenyl-5-hexen-3-ol
  参考文献：
  名称：

  Stereocontrolled palladium-catalysed umpolung allylation of aldehydes with allyl acetates

  摘要：

  In the present work the stereocontrolled palladium-catalysed umpolung allylation of aldehydes is described. Allyl acetates are in situ transformed into the corresponding allyl boronates, which directly react with aldehydes. The question of stereocontrol is raised by employing (a) chiral boronating agents (reagent control) and by (b) utilising chiral aldehydes (substrate control). These studies reveal that the approach based on substrate control is superior to the former one with respect to yields and stereo-selectivity. Remarkably, this umpolung protocol often yields the 4,5-syn products in high selectivity, which is unprecedented for direct crotylations. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.133

文献信息

• Highly diastereoselective reactions of (E)-cinnamyl chloride with aldehydes mediated by tin and aluminium
  作者：James M. Coxon、Stephen J. van Eyk、Peter J. Steel

  DOI：10.1016/s0040-4039(00)95103-7

  日期：1985.1

  The reactions of (E)-cinnamyl chloride with aldehydes in H2O: THF: HBr in the presence of tin and aluminium powders proceed with very high stereoselectivity.

  在锡和铝粉的存在下，（E）-肉桂酰氯与醛在H 2 O：THF：HBr中的反应以很高的立体选择性进行。
• Diastereoselectivity, diastereofacial selectivity and regioselectivity in the reactions of cannamyl chloride with aldehydes mediated by tin and aluminium
  作者：James M. Coxon、Stephen J. van Eyk、Peter J. Steel

  DOI：10.1016/0040-4020(89)80014-6

  日期：1989.1

  The reaction of cinnamyl chloride witha scrics of alkyl and alkyl aldchydes mediated by tin and aluminium has been shown to be regiosclective and threo diastercosclective. For aldehydes with chirality adjacent to the carbonyl function some diastcrcofacial selectivity is observed. Conjugated aldchyydcs undergo regioselective 1,2-addition to the carbonyl.

  的肉桂基氯与反应一个烷基的scrics和由锡和铝介导的烷基aldchydes已被证明是regiosclective和苏diastercosclective。对于具有与羰基官能团相邻的手性的醛，观察到一些舒张表面选择性。共轭的醛基环糊精经过羰基的1,2-区域选择性加成。
• COXON, JAMES M.;VAN, BYK STEPHEN J.;STEEL, PETER J., TETRAHEDRON, 45,(1989) N, C. 1029-1041
  作者：COXON, JAMES M.、VAN, BYK STEPHEN J.、STEEL, PETER J.

  DOI：——

  日期：——
• COXON, J. M.;EYK, S. J. VAN;STEEL, P. J., TETRAHEDRON LETT., 1985, 26, N 49, 6121-6124
  作者：COXON, J. M.、EYK, S. J. VAN、STEEL, P. J.

  DOI：——

  日期：——
• Stereocontrolled palladium-catalysed umpolung allylation of aldehydes with allyl acetates
  作者：Monika Vogt、Sascha Ceylan、Andreas Kirschning

  DOI：10.1016/j.tet.2010.04.133

  日期：2010.8

  In the present work the stereocontrolled palladium-catalysed umpolung allylation of aldehydes is described. Allyl acetates are in situ transformed into the corresponding allyl boronates, which directly react with aldehydes. The question of stereocontrol is raised by employing (a) chiral boronating agents (reagent control) and by (b) utilising chiral aldehydes (substrate control). These studies reveal that the approach based on substrate control is superior to the former one with respect to yields and stereo-selectivity. Remarkably, this umpolung protocol often yields the 4,5-syn products in high selectivity, which is unprecedented for direct crotylations. (C) 2010 Elsevier Ltd. All rights reserved.