(3S)-3-benzamido-3-(4-methoxyphenyl)propanal | 562100-15-6

• 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: (3S)-3-benzamido-3-(4-methoxyphenyl)propanal
• 英文别名: (S)-3-benzoylamino-3-(4-methoxyphenyl)propanal；(S)-N-[1-(4-methoxyphenyl)-2-formylethyl]benzamide；N-[(1S)-1-(4-methoxyphenyl)-3-oxopropyl]benzamide
• CAS: 562100-15-6
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: ISFWBUQHBYHSDY-INIZCTEOSA-N

物化性质

• 沸点：
  508.4±50.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S)-3-benzamido-3-(4-methoxyphenyl)propanal 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (S)-3-benzoylamino-3-(4-methoxyphenyl)propanol
  参考文献：
  名称：

  乙醛的直接有机催化曼尼希反应：一种改进的催化剂和来自计算研究的机理见解。

  摘要：

  DOI：

  10.1002/anie.200802073
• 作为产物：
  描述：

  N-(4-methoxybenzylidene)benzamide 在 tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium 、 Amberlyst-15 H⁽¹⁺⁾ 作用下， 以 环己烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 192.0h， 生成 (3S)-3-benzamido-3-(4-methoxyphenyl)propanal
  参考文献：
  名称：

  Novel Use of N-Benzoyl-N,O-acetals as N-Acylimine Equivalents in Asymmetric Heterocycloaddition:  An Extended Enantioselective Pathway to β-Benzamido Aldehydes

  摘要：

  For the first time, easily available N-(alpha-methoxyalkyl)amides were successfully used as synthetic equivalents of N-acylimines in an asymmetric heterocycloaddition process. The facial-controlled formation of 6-alkoxydihydrooxazines was thus achieved by SnCl4-promoted heterocycloaddition of (R)-O-vinyl pantolactone. By simple acidic hydrolysis of the crude heteroadducts, new beta-aryl- and beta-alkyl-substituted benzamido aldehydes were thus obtained in good overall yields with high enantioselectivities.

  DOI：

  10.1021/jo0203138

文献信息

• Asymmetric synthesis of α- and β-amino acids by diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl)imines
  作者：Raquel Almansa、Juan F. Collados、David Guijarro、Miguel Yus

  DOI：10.1016/j.tetasy.2010.03.046

  日期：2010.6

  The diastereoselective addition of triorganozincates to (R)-N-(tert-butanesulfinyl)imines has been used as a key step to achieve the synthesis of highly enantiomerically enriched N-protected alpha- and beta-amino acids. Desulfinylation of the addition products followed by benzoylation of the nitrogen atom of the obtained primary amines and oxidation of one of the substituents on the carbon atom connected to the nitrogen complete the sequence. Using the same configuration in the sulfinyl chiral auxiliary, alpha-amino acids with the (R) or the (S) configuration can be prepared by choosing the proper combination of imine and organozincate. alpha,alpha-Disubstituted alpha-amino esters with high enantiomeric purity can also be prepared when a-imino esters are the starting substrates. (C) 2010 Elsevier Ltd. All rights reserved.
• Direct Organocatalytic Mannich Reaction of Acetaldehyde: An Improved Catalyst and Mechanistic Insight from a Computational Study
  作者：Yujiro Hayashi、Tsubasa Okano、Takahiko Itoh、Tatsuya Urushima、Hayato Ishikawa、Tadafumi Uchimaru

  DOI：10.1002/anie.200802073

  日期：2008.11.10
• Novel Use of <i>N</i>-Benzoyl-<i>N,O</i>-acetals as <i>N</i>-Acylimine Equivalents in Asymmetric Heterocycloaddition:  An Extended Enantioselective Pathway to β-Benzamido Aldehydes
  作者：Patricia Gizecki、Robert Dhal、Céline Poulard、Pascal Gosselin、Gilles Dujardin

  DOI：10.1021/jo0203138

  日期：2003.5.1

  For the first time, easily available N-(alpha-methoxyalkyl)amides were successfully used as synthetic equivalents of N-acylimines in an asymmetric heterocycloaddition process. The facial-controlled formation of 6-alkoxydihydrooxazines was thus achieved by SnCl4-promoted heterocycloaddition of (R)-O-vinyl pantolactone. By simple acidic hydrolysis of the crude heteroadducts, new beta-aryl- and beta-alkyl-substituted benzamido aldehydes were thus obtained in good overall yields with high enantioselectivities.