(S)-2-propyl-pent-4-enoic acid | 117039-65-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-2-propyl-pent-4-enoic acid
• 英文别名: (S)-2-propylpent-4-enoic acid；4-Pentanoic acid, 2-propyl-, (S)-；(2S)-2-propylpent-4-enoic acid
• CAS: 117039-65-3
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: UMYDNZXEHYSVFY-SSDOTTSWSA-N

物化性质

• 沸点：
  228.8±9.0 °C(Predicted)
• 密度：
  0.943±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  R(+)-alpha-甲基苄胺 、 (S)-2-propyl-pent-4-enoic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Electrophilic Rearrangements of Chiral Amides: A Traceless Asymmetric α-Allylation

  摘要：

  A one-pot protocol for the asymmetric alpha-allylation reaction is reported relying on a key efficient asymmetric Claisen rearrangement, triggered by electrophilic activation of chiral pseudoephedrine amides. Subsequent reduction or hydrolysis of the resulting iminium ions provides highly enantioenriched alpha-allylic aldehydes or carboxylic acids in a traceless manner. Compared to traditional alternatives which make use of strongly basic conditions, the work presented herein displays unprecedented functional group tolerance.

  DOI：

  10.1021/ja408856p
• 作为产物：
  描述：

  (1S,2S)-N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methylpentanamide 在 2-氟吡啶 、 硫酸 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 36.5h， 生成 (3S,5S)-5-methyl-3-propyldihydrofuran-2(3H)-one 、 (S)-2-propyl-pent-4-enoic acid
  参考文献：
  名称：

  Electrophilic Rearrangements of Chiral Amides: A Traceless Asymmetric α-Allylation

  摘要：

  A one-pot protocol for the asymmetric alpha-allylation reaction is reported relying on a key efficient asymmetric Claisen rearrangement, triggered by electrophilic activation of chiral pseudoephedrine amides. Subsequent reduction or hydrolysis of the resulting iminium ions provides highly enantioenriched alpha-allylic aldehydes or carboxylic acids in a traceless manner. Compared to traditional alternatives which make use of strongly basic conditions, the work presented herein displays unprecedented functional group tolerance.

  DOI：

  10.1021/ja408856p

文献信息

• Enantioselective radical allylation reactions using chiral lanthanide Lewis acids
  作者：Mukund P. Sibi、Shankar Manyem、Rajesh Subramaniam

  DOI：10.1016/j.tet.2003.07.019

  日期：2003.12

  Radical additions to oxazolidinone acrylate followed by allyl trapping were studied with chiral Lewis acids derived from lanthanide salts. Chiral ligands were evaluated to establish the α-stereocenter. Ligands with a prolinol framework along with achiral additives proved to be effective. The observed trends are compared with those in the literature.

  用衍生自镧系元素盐的手性路易斯酸研究了向丙烯酸恶唑烷酮丙烯酸酯的自由基加成反应，然后进行烯丙基捕集。评价手性配体以建立α-立体中心。具有脯氨醇骨架和非手性添加剂的配体被证明是有效的。将观察到的趋势与文献中的趋势进行比较。