ethyl (Z)-2-[(1-hydroxy-1-methylpropyl)]-3-phenylpropenoate

• 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: ethyl (Z)-2-[(1-hydroxy-1-methylpropyl)]-3-phenylpropenoate
• 英文别名: ethyl (2Z)-2-(1-hydroxy-1-methylpropyl)-3-phenylacrylate；ethyl (2Z)-2-benzylidene-3-hydroxy-3-methylpentanoate
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: OQYDSIFGZHISJZ-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  α-氯代肉桂醛 在 sodium dihydrogenphosphate 、 三甲基氯硅烷 、 samarium diiodide 、 sodium perchlorate 、 双氧水 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 13.0h， 生成 ethyl (Z)-2-[(1-hydroxy-1-methylpropyl)]-3-phenylpropenoate
  参考文献：
  名称：

  α-卤代-α，β-不饱和酯与SmI 2促进的酮或醛的高度选择性反应：一种有效的Baylis-Hillman加合物的替代途径

  摘要：

  二碘化sa促进芳香族或脂肪族β-取代-α-卤代-α，β-不饱和酯1或3加到酮（在THF中）和醛（在乙腈中）上，导致（Z）-2-（1-羟基烷基）-2,3-链烯酸酯2和4的收率和立体选择性很高。该方法构成了Baylis-Hillman加合物合成的有效且有价值的替代方法。提出了一种机制来解释这种转变。

  DOI：

  10.1021/jo0504969

文献信息

• Vinylalumination for the Synthesis of Functionalized Allyl Alcohols, Vinylepoxides, and α-Alkylidene-β-hydroxy-γ-lactones
  作者：P. Veeraraghavan Ramachandran、Michael T. Rudd、Thomas E. Burghardt、M. Venkat Ram Reddy

  DOI：10.1021/jo034954u

  日期：2003.11.1

  A modified hydroalumination protocol for the preparation of [alpha-(ethoxycarbonyl)vinyl]diisobutyl-aluminum and its beta-methyl or -phenyl analogues was developed. These vinylaluminum reagents react with aldehydes and ketones to provide the corresponding functionalized allyl alcohols in good to excellent yields. Perfluoroalkyl and -aryl carbonyl compounds, alpha-keto esters, alpha-acyl cyanides, and alpha-acetylenic ketones provide the corresponding alpha-hydroxyalkenes in high yields. The allyl alcohol product ratios from the vinylalumination of unsymmetrical alpha-diketones with [alpha-(ethoxycarbonyl)vinyl] diisobutylaluminum and its beta-methyl or -phenyl analogues depend on the steric and electronic environments of the ketones as well as the reagents. The products from the vinylalumination of alpha-bromoaldehydes and -ketones were cyclized With K2CO3 or KF under nonaqueous conditions to provide functionalized vinylepoxides in high yields. Vinylaluminations of keto-protected pyruvaldehyde provided the products, which were converted to alpha-alkylidene-beta-hydroxy-gamma-lactones.
• Ramachandran, P. Veeraraghavan; Reddy, M. Venkat Ram; Rudd, Michael T., Chemical Communications, 1999, # 19, p. 1979 - 1980
  作者：Ramachandran, P. Veeraraghavan、Reddy, M. Venkat Ram、Rudd, Michael T.

  DOI：——

  日期：——
• Highly Selective Reaction of α-Halo-α,β-unsaturated Esters with Ketones or Aldehydes Promoted by SmI₂:  An Efficient Alternative Access to Baylis−Hillman Adducts
  作者：José M. Concellón、Mónica Huerta

  DOI：10.1021/jo0504969

  日期：2005.6.1

  A samarium diiodide promoted addition of aromatic or aliphatic β-substituted-α-halo-α,β-unsaturated esters 1 or 3 to both ketones (in THF) and aldehydes (in acetonitrile) led to (Z)-2-(1-hydroxyalkyl)-2,3-alkenoates 2 and 4 in good yields and very high stereoselectivity. This method constitutes an efficient and valuable alternative to the synthesis of Baylis−Hillman adducts. A mechanism is proposed

  二碘化sa促进芳香族或脂肪族β-取代-α-卤代-α，β-不饱和酯1或3加到酮（在THF中）和醛（在乙腈中）上，导致（Z）-2-（1-羟基烷基）-2,3-链烯酸酯2和4的收率和立体选择性很高。该方法构成了Baylis-Hillman加合物合成的有效且有价值的替代方法。提出了一种机制来解释这种转变。