(E)-3-phenylacrylic acid [(1S)-endo]bornyl ester | 77942-64-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-phenylacrylic acid [(1S)-endo]bornyl ester
• 英文别名: (S)-(-)-bornyl cinnamate；(-)-bornyl cinnamate；2-Propenoic acid, 3-phenyl-, 1,7,7-trimethylbicyclo(2.2.1)hept-2-yl ester, endo-；[(1S,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] (E)-3-phenylprop-2-enoate
• CAS: 77942-64-4
• 化学式: C₁₉H₂₄O₂
• 分子量: 284.398
• InChiKey: ACTRLDZRLKIJEH-FXOMATFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  (E)-3-phenylacrylic acid [(1S)-endo]bornyl ester 在 lithium perchlorate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以98%的产率得到[(1S,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] (1S,2R,3S)-5-oxo-2,3-diphenylcyclopentane-1-carboxylate
  参考文献：
  名称：

  Utley, James H. P.; Guellue, Mustafa; Motevalli, Majid, Journal of the Chemical Society. Perkin transactions I, 1995, # 15, p. 1961 - 1970

  摘要：

  DOI：
• 作为产物：
  描述：

  肉桂酸 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 49.5h， 生成 (E)-3-phenylacrylic acid [(1S)-endo]bornyl ester
  参考文献：
  名称：

  Conjugate addition of aryl nucleophiles to α,β-unsaturated cinnamic acid derivatives containing Evans type chiral auxiliaries

  摘要：

  Cinnamides containing oxazolidin-2-one type auxiliaries have been prepared. A novel pathway to chiral 4-aryl-6-methyl-3,4-dihydrocoumrines via the asymmetric conjugate addition of arylmagnesium bromides to these cinnamides is described. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.07.003

文献信息

• Stereoselective Hydrocoupling of Cinnamic Acid Esters by Electroreduction:  Application to Asymmetric Synthesis of Hydrodimers
  作者：Naoki Kise、Shumei Iitaka、Keisuke Iwasaki、Nasuo Ueda

  DOI：10.1021/jo026183k

  日期：2002.11.1

  The electroreduction of Ar-substituted methyl cinnamates in acetonitrile gave all-trans cyclized hydrodimers stereoselectively (58 approximately 90% de). In all cases, small amounts (<10% yield) of meso hydrodimers were also formed. The electrolysis was performed conveniently using an undivided cell at a constant current. The transition states for the hydrocoupling were calculated with semiempirical

  Ar-取代的肉桂酸甲酯在乙腈中的电还原立体选择性地产生了全反式环化的二聚体（58约为90％de）。在所有情况下，也会形成少量（<10％的收率）内消旋二聚体。电解是使用恒定电压的不分隔电池方便地进行的。用半经验方法计算了水耦合的过渡态。全反式环化的二聚体被转化为C（2）对称的dl-3,4-二芳基己二酸和反式3,4-二芳基环戊烷。由（1R）-（+）-樟脑制备的手性辅助[（1R）-exo] -3-exo-（二苯甲基）冰片，对于通过电还原将肉桂酸酯进行立体选择性加氢偶联非常有效。（3R，4R）-3,4-二芳基己二酸酯和（3R，4R）-3,4-二芳基己烷-1
• Fussing, Ingrid; Guellue, Mustafa; Hammerich, Ole, Journal of the Chemical Society. Perkin transactions II, 1996, # 4, p. 649 - 658
  作者：Fussing, Ingrid、Guellue, Mustafa、Hammerich, Ole、Hussain, Abid、Nielsen, Merete Folmer、Utley, James H. P.

  DOI：——

  日期：——
• Utley, James H. P.; Guellue, Mustafa; Motevalli, Majid, Journal of the Chemical Society. Perkin transactions I, 1995, # 15, p. 1961 - 1970
  作者：Utley, James H. P.、Guellue, Mustafa、Motevalli, Majid

  DOI：——

  日期：——
• Conjugate addition of aryl nucleophiles to α,β-unsaturated cinnamic acid derivatives containing Evans type chiral auxiliaries
  作者：Zigmārs Leitis、Viesturs Lūsis

  DOI：10.1016/j.tetasy.2016.07.003

  日期：2016.10

  Cinnamides containing oxazolidin-2-one type auxiliaries have been prepared. A novel pathway to chiral 4-aryl-6-methyl-3,4-dihydrocoumrines via the asymmetric conjugate addition of arylmagnesium bromides to these cinnamides is described. (C) 2016 Elsevier Ltd. All rights reserved.