tert-butyl (E)-4-phenylpent-2-enoate | 140184-80-1

• 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: tert-butyl (E)-4-phenylpent-2-enoate
• CAS: 140184-80-1
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: XBJLCFCRWPQXKA-ZHACJKMWSA-N

物化性质

• 沸点：
  309.9±21.0 °C(Predicted)
• 密度：
  0.985±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  tert-butyl (E)-4-phenylpent-2-enoate 在 lithium aluminium tetrahydride 、 正丁基锂 、 N,N-二异丙基乙胺 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Highly Diastereoselective Conjugate Addition of Lithium Dialkylamides to α,β-Unsaturated Esters Having a Chiral Center at the γ-Position

  摘要：

  The conjugate addition of lithium amides 2 to tert-butyl 4-(OR)-substituted-2-pentenoates 1 produced a mixture of the syn-and anti-amino esters (3 and 4) in high yields. Sterically bulky OR groups, such as trityloxy and tert-butyldiphenylsilyloxy, gave the syn diastereomer 3 either exclusively or predominantly. The syn-selectivity may be explained by a modified Felkin-Anh model. The use of tert-butyldimethylsilyloxy as an OR group afforded a nearly 1:1 mixture of diastereoisomers, and the use of the smallest MeO group produced a 63:37 mixture of the syn 3 and anti isomer 4. The presence of Me group at the alpha-position (C-2 position) of the enoate enhanced the syn diastereoselectivity up to 100%; the conjugate addition to tert-butyl 4-methoxy-2-methyl-2-pentenoate (17) gave the syn-isomer 18 exclusively. This enhancement may be explained by the combination of chelation and allylic strain model 19 in which the smallest H orients inside to avoid an allylic strain. A phenyl group at the gamma-position enhanced the anti selectivity in the case of gamma-alkoxy-alpha,beta-enoates such as isopropyl 4-[(tert-butyldimethylsilyl)oxy]-4-phenyl-2-buteonoate (20), and in the case of gamma-alkyl-alpha,beta-enoates such as tert-butyl 4-phenyl-2-pentenoate (27).

  DOI：

  10.1021/jo970435d
• 作为产物：
  描述：

  2-苯基丙醛 、 二乙基膦酰基乙酸叔丁酯 在 甲基溴化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.25h， 以100%的产率得到tert-butyl (E)-4-phenylpent-2-enoate
  参考文献：
  名称：

  甲基溴化镁促进了高度（E）选择性的Wadsworth-Emmons反应。

  摘要：

  对一系列直链和支链脂族，取代芳族化合物进行非常高度（E）选择性的Wadsworth-Emmons反应[（E）:( Z）选择性在某些情况下超过180：1的反应）的实验简单方法，报道了通过与烷基二乙基膦酰基乙酸酯和MeMgBr反应生成的对碱敏感的醛。

  DOI：

  10.1021/ol802212e

文献信息

• Carbonyl olefination with a-stannyl ester enolates: A new synthesis of α,β-unsaturated esters
  作者：Antonio Zapata、Beatriz M. Núñez、Fernando J. Ferrer

  DOI：10.1016/0022-328x(92)80013-n

  日期：1992.2

  The reaction of α-stannyl ester enolates with carbonyl compounds is described. α,β-Unsaturated esters are obtained in good yields. A reaction mec

  描述了α-锡烷基酯烯酸酯与羰基化合物的反应。以高收率获得α，β-不饱和酯。反应机制
• Highly (<i>E</i>)-Selective Wadsworth−Emmons Reactions Promoted by Methylmagnesium Bromide
  作者：Timothy D. W. Claridge、Stephen G. Davies、James A. Lee、Rebecca L. Nicholson、Paul M. Roberts、Angela J. Russell、Andrew D. Smith、Steven M. Toms

  DOI：10.1021/ol802212e

  日期：2008.12.4

  An experimentally simple protocol for the very highly (E)-selective Wadsworth-Emmons reaction [(E):(Z) selectivities in excess of 180:1 in some cases] of a range of straight-chain and branched aliphatic, substituted aromatic, and base-sensitive aldehydes via reaction with an alkyl diethylphosphonoacetate and MeMgBr is reported.

  对一系列直链和支链脂族，取代芳族化合物进行非常高度（E）选择性的Wadsworth-Emmons反应[（E）:( Z）选择性在某些情况下超过180：1的反应）的实验简单方法，报道了通过与烷基二乙基膦酰基乙酸酯和MeMgBr反应生成的对碱敏感的醛。
• Highly Diastereoselective Conjugate Addition of Lithium Dialkylamides to α,β-Unsaturated Esters Having a Chiral Center at the γ-Position
  作者：Naoki Asao、Takashi Shimada、Tomoko Sudo、Naofumi Tsukada、Kazuhiko Yazawa、Young Soo Gyoung、Tadao Uyehara、Yoshinori Yamamoto

  DOI：10.1021/jo970435d

  日期：1997.9.1

  The conjugate addition of lithium amides 2 to tert-butyl 4-(OR)-substituted-2-pentenoates 1 produced a mixture of the syn-and anti-amino esters (3 and 4) in high yields. Sterically bulky OR groups, such as trityloxy and tert-butyldiphenylsilyloxy, gave the syn diastereomer 3 either exclusively or predominantly. The syn-selectivity may be explained by a modified Felkin-Anh model. The use of tert-butyldimethylsilyloxy as an OR group afforded a nearly 1:1 mixture of diastereoisomers, and the use of the smallest MeO group produced a 63:37 mixture of the syn 3 and anti isomer 4. The presence of Me group at the alpha-position (C-2 position) of the enoate enhanced the syn diastereoselectivity up to 100%; the conjugate addition to tert-butyl 4-methoxy-2-methyl-2-pentenoate (17) gave the syn-isomer 18 exclusively. This enhancement may be explained by the combination of chelation and allylic strain model 19 in which the smallest H orients inside to avoid an allylic strain. A phenyl group at the gamma-position enhanced the anti selectivity in the case of gamma-alkoxy-alpha,beta-enoates such as isopropyl 4-[(tert-butyldimethylsilyl)oxy]-4-phenyl-2-buteonoate (20), and in the case of gamma-alkyl-alpha,beta-enoates such as tert-butyl 4-phenyl-2-pentenoate (27).