(S)-3-(2-methoxyphenyl)-3-phenylpropanal | 92804-31-4

• 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-(2-methoxyphenyl)-3-phenylpropanal
• 英文别名: (3S)-3-(2-methoxyphenyl)-3-phenylpropanal
• CAS: 92804-31-4
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: NOKRZJHWDUUKMG-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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)-3-(2-methoxyphenyl)-3-phenylpropanal 在 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 3-(2-methoxyphenyl)-3-phenyl-1-propanol
  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：

  2-甲氧基肉桂醛 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-(2-methoxyphenyl)-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。
• 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).
• Highly enantioselective 1,4-addition of arylzinc reagents to 3-arylpropenals catalyzed by a rhodium–binap complex in the presence of chlorotrimethylsilane
  作者：Norihito Tokunaga、Tamio Hayashi

  DOI：10.1016/j.tetasy.2006.01.036

  日期：2006.2

  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.