(S)-2-(4-methoxyphenyl)propanal | 147922-82-5

• 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: (S)-2-(4-methoxyphenyl)propanal
• 英文别名: (S)-2-(p-Methoxyphenyl)propanal；(2S)-2-(4-methoxyphenyl)propanal
• CAS: 147922-82-5
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: JDZPCXLQZLJIPR-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(4-methoxyphenyl)propanal 在 4-二甲氨基吡啶 、 正丁基锂 、 二甲基亚砜 、 三乙胺 、 六甲基二硅氮烷 作用下， 以 乙醚 为溶剂， -50.0~500.0 ℃ 、1.33 Pa 条件下， 反应 7.5h， 生成 (4S,5R,6S)-2,4-Dimethyl-6-(p-methoxyphenyl)-5-(trimethylsiloxy)-1-hepten-3-one
  参考文献：
  名称：

  Efficient and highly stereoselective syntheses of enantiomerically enriched C(1)-C(7) subunits of erythronolides

  摘要：

  Stereocontrolled efficient syntheses of the C(1)-C(7) fragments of deoxyerythronolide and erythronolide seco acids are described. The key step of these syntheses involves a highly stereoselective aldol condensation between an enantiomerically enriched 2-arylpropanal and the lithium enolate of the racemic 2-methyl-5-norbornenyl ethyl ketone, which establishes in one operation the relative and absolute configurations of the three stereocenters C(2), C(3), and C(4). After syn-selective reductions of the carbonyl group, the configuration required at carbon C(6) was introduced by highly selective reactions carried out on the double bond regenerated by a thermal cycloreversion.

  DOI：

  10.1021/jo00063a009
• 作为产物：
  描述：

  (S)-2-(4-methoxyphenyl)propan-1-ol 以86%的产率得到(S)-2-(4-methoxyphenyl)propanal
  参考文献：
  名称：

  Efficient and highly stereoselective syntheses of enantiomerically enriched C(1)-C(7) subunits of erythronolides

  摘要：

  Stereocontrolled efficient syntheses of the C(1)-C(7) fragments of deoxyerythronolide and erythronolide seco acids are described. The key step of these syntheses involves a highly stereoselective aldol condensation between an enantiomerically enriched 2-arylpropanal and the lithium enolate of the racemic 2-methyl-5-norbornenyl ethyl ketone, which establishes in one operation the relative and absolute configurations of the three stereocenters C(2), C(3), and C(4). After syn-selective reductions of the carbonyl group, the configuration required at carbon C(6) was introduced by highly selective reactions carried out on the double bond regenerated by a thermal cycloreversion.

  DOI：

  10.1021/jo00063a009

文献信息

• Asymmetric hydroformylation catalyzed by homogeneous and polymer-supported platinum complexes containing chiral phosphine ligands
  作者：Giovanni Parrinello、J. K. Stille

  DOI：10.1021/ja00257a036

  日期：1987.11

  Hydroformylation de styrene, isobutyl-4styrene, vinyl-2 et methoxy-6 vinyl-2-naphtalenes, acetate de vinyle, methacrylate de methyle, norbornene, en presence de chlorure stanneux et en presence d'orthoformiate de triethyle

  加氢甲酰化脱苯乙烯、异丁基-4 苯乙烯、乙烯基-2 和甲氧基-6 乙烯基-2-萘、乙酸乙烯酯、甲基丙烯酸酯、降冰片烯、氯化物 stanneux 和三乙基正甲酸酯的存在
• Easily Accessible and Highly Tunable Bisphosphine Ligands for Asymmetric Hydroformylation of Terminal and Internal Alkenes
  作者：Kun Xu、Xin Zheng、Zhiyong Wang、Xumu Zhang

  DOI：10.1002/chem.201304684

  日期：2014.4.7

  An efficient methodology for synthesizing a small library of easily tunable and sterically bulky ligands for asymmetric hydroformylation (AHF) has been reported. Five groups of alkene substrates have been tested with excellent conversions, moderate‐to‐excellent regio‐ and enantioselectivities. Among the best result of the reported literature, application of ligand 1 c in the highly selective AHF of

  已经报道了一种有效的方法，该方法可合成用于不对称加氢甲酰化（AHF）的易于调节且空间庞大的配体的小文库。已测试了五组烯烃底物，具有优异的转化率，中等至出色的区域选择性和对映选择性。在所报道文献的最佳结果中，将配体1c应用于具有挑战性的底物2,5-二氢呋喃的高选择性AHF中，产生了几乎一种异构体，转化率高达99％，对映体过量（ee）高达92％ 。使用相同的配体可实现二氢吡咯底物的高度对映选择性AHF，ee高达95％  ，β-异构体/α-异构体比率高达> 1:50。
• Highly Enantioselective Hydroformylation of Aryl Alkenes with Diazaphospholane Ligands
  作者：Avery L. Watkins、Brian G. Hashiguchi、Clark R. Landis

  DOI：10.1021/ol801723a

  日期：2008.10.16

  Asymmetric, rhodium-catalyzed hydroformylation of terminal and internal aryl alkenes with diazaphospholane ligands is reported. Under partially optimized reaction conditions, high enantioselectivity (>90% ee) and regioselectivities (up to 65:1 alpha:beta) are obtained for most substrates. For terminal alkenes, both enantioselectivity and regioselectivity are proportional to the carbon monoxide partial

  报道了带有二氮杂磷烷配体的铑和不饱和铑催化的末端和内部芳基烯烃的加氢甲酰化反应。在部分优化的反应条件下，大多数底​​物均具有高对映选择性（> 90％ee）和区域选择性（最高65：1α：β）。对于末端烯烃，对映选择性和区域选择性均与一氧化碳分压成比例，但与氢压无关。对位取代的苯乙烯衍生物的加氢甲酰化作用对带有吸电子取代基的底物具有最高的区域选择性。Hammett分析得出区域选择性呈正线性相关。
• Rhodium/phospholane–phosphite catalysts give unusually high regioselectivity in the enantioselective hydroformylation of vinyl arenes
  作者：Gary M. Noonan、Christopher J. Cobley、Thomas Mahoney、Matthew L. Clarke

  DOI：10.1039/c3cc48823c

  日期：——

  Using the phospholane–phosphite ligand shown, chemoselectivity to aldehydes, regioselectivity and enantioselectivity are all very high, even using low catalyst loadings and with no solvent.

  使用所示的磷酚烷-磷酸酯配体，对醛的化学选择性、位置选择性和对映选择性都非常高，甚至在低催化剂负载和无溶剂的情况下也是如此。
• Formation of multi-stereogenic centers using a catalytic diastereoselective Henry reaction
  作者：Takayoshi Arai、Yoshinori Taneda、Yoko Endo

  DOI：10.1039/c0cc03022h

  日期：——

  A diastereoselective Henry reaction of chiral aldehydes with nitroalkanes was developed using a chiral sulfonyldiamine (L1)-CuCl complex. The reaction of (R)-2-phenylpropanal and nitromethane was smoothly catalyzed by the (S,S,S)-L1-CuCl complex to give the adduct with 99/1 syn/anti selectivity in 99% ee. In the reaction of (S)-2-phenylpropanal and nitroethane, the (R,R,R)-L1-CuCl catalyst yielded

  使用手性磺酰基二胺（L1）-CuCl配合物开发了手性醛与硝基烷烃的非对映选择性亨利反应。（R）-2-苯基丙醛与硝基甲烷的反应被（S，S，S）-L 1 -CuCl配合物平稳地催化，从而在99％ee中得到具有99/1顺/反选择性的加合物。在（S）-2-苯基丙醛和硝基乙烷的反应中，（R，R，R）-L1-CuCl催化剂在高度同位选择的亨利反应中产生了预期的三个连续的立体中心。