(3R)-3-phenyl-hex-5-enoic acid | 127393-10-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (3R)-3-phenyl-hex-5-enoic acid
• 英文别名: (R)-3-phenyl-5-hexenoic acid；(3R)-3-phenylhex-5-enoic acid
• CAS: 127393-10-6
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: KARGDSIBBUXAAF-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (3R)-3-phenyl-hex-5-enoic acid 在 4 A molecular sieve 、 碘 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以20%的产率得到(4R,6S)-6-iodomethyl-4-phenyltetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  氨基-Cope重排的应用：四氢吡喃，δ-内酯和哌啶靶标的合成。

  摘要：

  我们报告了一些手性四氢吡喃和δ-内酯目标的新型方法，该方法利用不对称氨基-Cope重排作为关键的合成步骤。氨基-Cope重排化学的产物也已经用于接近哌啶的靶标，进一步证明了该方法的潜力。

  DOI：

  10.1039/b416179c
• 作为产物：
  描述：

  (4R,5S)-1,5-dimethyl-3-[(2E)-3-phenyl-2-propenoyl]-4-phenyl-2-imidazolidinone 在 lithium hydroxide 、 二甲基硫 、 copper(I) bromide 作用下， 生成 (3R)-3-phenyl-hex-5-enoic acid
  参考文献：
  名称：

  Addition diastéréosélective d'allyl cuprates à des imides chirales insaturées

  摘要：

  DOI：

  10.1016/0022-328x(90)85369-a

文献信息

• Regio-, stereo-, and enantioselectivity in the electrophilic reactions of 2-amino-4-phenyl-3-butenenitriles
  作者：Chih Jung Chang、Jim Min Fang、Li Fan Liao

  DOI：10.1021/jo00059a027

  日期：1993.3

  The allylic anion generated from 2-(N-methylanilino)-4-phenyl-3-butenenitrile (1) reacted with iodomethane and 3-bromo-1-chloropropane in THF/HMPA to give the gamma-substitution products exclusively, predominantly in the 2Z-configuration. Substitution of the N-methylanilino group with the methyl ether of L-(-)-ephedrine resulted in the generation of chiral aminonitrile 2. Lithiated 2 reacted sluggishly in THF with allyl bromide and benzyl chloride in the absence of HMPA to give the gamma-substitution products predominantly in the 2Z-configuration, with little diastereoselectivity. The aminonitrile 3 prepared from cinnamaldehyde, L-(-)-ephedrine, and KCN was lithiated with 2 equiv of LDA resulting in high facial selectivity (76-100% diastereomeric excess) in alkylations in the presence of HMPA and LiI. Lithiated 3 reacted with propionaldehyde, benzaldehyde, and p-bromobenzaldehyde at-78-degrees-C to give the gamma-addition products, predominantly in the 4R-configuration (64-78% de). The stereochemistry of the isomers of each product was determined by chemical correlation and spectral methods including analyses of the CD spectra and X-ray diffraction. A bicyclic transition state C wherein lithium is chelated by both amino and alkoxy groups is proposed to interpret the observed stereoselectivity.
• Chang Chih-Jung, Fang Jim-Min, Liao Li-Fan, J. Org. Chem., 58 (1993) N 7, S 1754-1761
  作者：Chang Chih-Jung, Fang Jim-Min, Liao Li-Fan

  DOI：——

  日期：——
• Applications of the amino-Cope rearrangement: synthesis of tetrahydropyran, δ-lactone and piperidine targets
  作者：Steven M. Allin、Munira Essat、Catarina Horro Pita、Robert D. Baird、Vickie McKee、Mark Elsegood、Mark Edgar、David M. Andrews、Pritom Shah、Ian Aspinall

  DOI：10.1039/b416179c

  日期：——

  We report a novel approach to some chiral tetrahydropyran and delta-lactone targets that utilizes the asymmetric amino-Cope rearrangement as a key synthetic step. Products of amino-Cope rearrangement chemistry have also been applied to access piperidine targets, further demonstrating the potential of the methodology.

  我们报告了一些手性四氢吡喃和δ-内酯目标的新型方法，该方法利用不对称氨基-Cope重排作为关键的合成步骤。氨基-Cope重排化学的产物也已经用于接近哌啶的靶标，进一步证明了该方法的潜力。
• Addition diastéréosélective d'allyl cuprates à des imides chirales insaturées
  作者：G. Pourcelot、O. Melnyk、Y. Besace、E. Stephan、P. Cresson

  DOI：10.1016/0022-328x(90)85369-a

  日期：1990.5