(S)-3-(4-fluorophenyl)-3-phenylpropanal | 863970-22-3

• 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)-3-(4-fluorophenyl)-3-phenylpropanal
• 英文别名: (3S)-3-(4-fluorophenyl)-3-phenylpropanal
• CAS: 863970-22-3
• 化学式: C₁₅H₁₃FO
• 分子量: 228.266
• InChiKey: MSEBKGTYEALKTO-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3-(4-fluorophenyl)-3-phenylpropanal 在 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (+)-(S)-3-(4-fluorophenyl)-3-phenylpropan-1-ol
  参考文献：
  名称：

  Highly enantioselective 1,4-addition of arylzinc reagents to 3-arylpropenals catalyzed by a rhodium–binap complex in the presence of chlorotrimethylsilane

  摘要：

  Asymmetric 1,4-addition of arylzinc chlorides to (E)-3-arylpropenals proceeded with high enantioselectivity in the presence of a rhodium/(R)-binap catalyst and chlorotrimethylsilane to give, after hydrolysis, high yields of the corresponding 3.3-diarylpropanals of 98-99% ee. The presence of the chlorosilane is essential for high yields of the 1,4-addition products. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.01.036
• 作为产物：
  描述：

  Zinc, chlorophenyl- 在 chiral binaphthyl-based rhodium potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 2.0h， 生成 (S)-3-(4-fluorophenyl)-3-phenylpropanal
  参考文献：
  名称：

  Highly enantioselective 1,4-addition of arylzinc reagents to 3-arylpropenals catalyzed by a rhodium–binap complex in the presence of chlorotrimethylsilane

  摘要：

  Asymmetric 1,4-addition of arylzinc chlorides to (E)-3-arylpropenals proceeded with high enantioselectivity in the presence of a rhodium/(R)-binap catalyst and chlorotrimethylsilane to give, after hydrolysis, high yields of the corresponding 3.3-diarylpropanals of 98-99% ee. The presence of the chlorosilane is essential for high yields of the 1,4-addition products. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.01.036

文献信息

• Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Aldehydes Catalyzed by a Chiral Diene–Rhodium Complex
  作者：Tamio Hayashi、Norihito Tokunaga、Kazuhiro Okamoto、Ryo Shintani

  DOI：10.1246/cl.2005.1480

  日期：2005.11

  Asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated aldehydes proceeded in the presence of a rhodium catalyst (3 mol %) coordinated with a chiral diene ligand ((R,R)-Bn-bod*) to give the corresponding β-arylaldehydes with perfect 1,4-selectivity and with 88–97% enantioselectivity.

  在铑催化剂（3摩尔%）与手性二烯配体（(R,R)-Bn-bod*）的配合下，芳基硼酸对α,β-不饱和醛的不对称1,4-加成反应顺利进行，生成相应的β-芳基醛，具有完美的1,4-选择性，并且表现出88至97%的立体选择性。
• Chiral dihydrobenzo[1,4]oxazines as catalysts for the asymmetric transfer-hydrogenation of α,β-unsaturated aldehydes
  作者：Christian Ebner、Andreas Pfaltz

  DOI：10.1016/j.tet.2011.10.051

  日期：2011.12

  A new class of organocatalysts based on the structure of 2,3-dihydrobenzo[1,4]oxazine was prepared and applied in the enantioselective transfer-hydrogenation of α,β-unsaturated aldehydes with Hantzsch ester as hydride donor. These catalysts proved to be particularly effective for the conjugate reduction of β,β-diaryl-substituted acrylaldehydes leading to saturated aldehydes bearing a stereogenic center

  制备了一种基于2,3-二氢苯并[1,4]恶嗪结构的新型有机催化剂，并将其用于以Hantzsch酯为氢化物供体的α，β-不饱和醛的对映选择性转移加氢。这些催化剂被证明对于共轭还原β，β-二芳基取代的丙烯醛特别有效，从而导致带有两个立体不同的芳基的立体异构中心的立体醛，对映选择性高达91％ee。
• Asymmetric Synthesis of 3,3-Diarylpropanals with Chiral Diene−Rhodium Catalysts
  作者：Jean-François Paquin、Christian Defieber、Corey R. J. Stephenson、Erick M. Carreira

  DOI：10.1021/ja053270w

  日期：2005.8.1

  A general route to enantioenriched 3,3-diarylpropanals is presented. These useful building blocks are prepared via an asymmetric rhodium-catalyzed conjugate addition of arylboronic acids to cinnamaldehyde derivatives in the presence of chiral dienes. The addition of both electron-poor as well as electron-rich boronic acids proceeds smoothly with various enals in 63-90% yield with high enantioselectivities (89-93% ee).