(R)-Phenyl-vinyloxy-acetic acid butyl ester | 164386-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-Phenyl-vinyloxy-acetic acid butyl ester
• 英文别名: butyl (2R)-2-ethenoxy-2-phenylacetate
• CAS: 164386-44-1
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: VRVOCHPSZIQFDN-CYBMUJFWSA-N

物化性质

• 沸点：
  323.0±35.0 °C(Predicted)
• 密度：
  1.032±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-Phenyl-vinyloxy-acetic acid butyl ester 在 sodium hydride 、 Eu(fod)3 作用下， 以 四氢呋喃 、 吡啶 、 盐酸 、 N,N-二甲基甲酰胺 、 甲苯 、 Petroleum ether 为溶剂， 反应 199.0h， 生成 (R)-1-苯基-1,2-乙二醇
  参考文献：
  名称：

  A New Synthetic Approach Toward (+)-Ambruticin Analogs: Preparation of a C10–C11cis-Isomer Fragment

  摘要：

  DOI：

  10.1002/(sici)1099-0690(199911)1999:11<2885::aid-ejoc2885>3.0.co;2-j
• 作为产物：
  描述：

  D-扁桃酸 在 mercury(II) diacetate 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 72.0h， 生成 (R)-Phenyl-vinyloxy-acetic acid butyl ester
  参考文献：
  名称：

  Synthèse asymétrique et configuration absolue de dihydropyranes substitués, par hétérocycloaddition intermoléculaire d'éthers vinyliques chiraux

  摘要：

  The alkyl vinyl ethers 2b-8b (deriving from the alcohols 2a-8a) smoothly reacted with methyl E-benzylidenepyruvate 10 in the presence of catalytic amounts of Eu(fod)(3) or Yb(fod)(3) in refluxing hexane, thus leading to the dihydropyran endo adducts 13-19 in high yields (80-95%). The endo-cycloadducts 13-17 were obtained with diastereofacial selectivities (ds) ranging from 76/24 to 87.5/12.5. Asymmetric induction was found to culminate with the vinyl ether (-)-7b deriving from n-butyl (R)-(-)-mandelate : the best ds (92.5/7.5) was obtained for the corresponding adduct 18 after 6 days at room temperature. The absolute configurations of the major isomers of the dihydropyrans 16-18, 20 and 21 were established by oxydative degradation to optically active alpha-phenylsuccinic acid derivatives.

  DOI：

  10.1016/s0040-4020(01)85370-9

文献信息

• Chiral enol ethers in carbohydrate chemistry: De novo synthesis of protected L-2-deoxy hexoses
  作者：Gilles Dujardin、Sandrine Rossignol、Eric Brown

  DOI：10.1016/0040-4039(96)00769-1

  日期：1996.6

  (3,4,6)Tri- and (3,4,)-di-O-benzyl-2-deoxy-L-glucose 8 and 12 have been de novo synthesized in a convergent seven-step sequence involving asymmtric endo heterocycloaddition of the new heterodiene, methyl (E)-benzyloxylmethylene pyruvate 2b with the O-vinyl mandelic ester (R)-(−)-3.

  （3,4,6）三-和（3,4） -二-O-苄基-2-脱氧-L-葡萄糖8和12已经从头在涉及的asymmtric内heterocycloaddition会聚七步序列合成新的杂二烯，甲基（E）-苄氧基亚甲基丙酮酸2b与O-乙烯基扁桃酸酯（R）-（-）- 3。
• An Improved Dienophile-Induced Access to Enantiopure 2,4-Dideoxysugar Lactones via Hetero Diels-Alder Reaction: Synthesis of the (+)-Lactone Moiety of Compactin
  作者：Gilles Dujardin、Sandrine Rossignol、Eric Brown

  DOI：10.1055/s-1998-4489

  日期：1998.5
• Synthèse asymétrique et configuration absolue de dihydropyranes substitués, par hétérocycloaddition intermoléculaire d'éthers vinyliques chiraux
  作者：Gilles Dujardin、Sandrine Rossignol、Samira Molato、Eric Brown

  DOI：10.1016/s0040-4020(01)85370-9

  日期：1994.1

  The alkyl vinyl ethers 2b-8b (deriving from the alcohols 2a-8a) smoothly reacted with methyl E-benzylidenepyruvate 10 in the presence of catalytic amounts of Eu(fod)(3) or Yb(fod)(3) in refluxing hexane, thus leading to the dihydropyran endo adducts 13-19 in high yields (80-95%). The endo-cycloadducts 13-17 were obtained with diastereofacial selectivities (ds) ranging from 76/24 to 87.5/12.5. Asymmetric induction was found to culminate with the vinyl ether (-)-7b deriving from n-butyl (R)-(-)-mandelate : the best ds (92.5/7.5) was obtained for the corresponding adduct 18 after 6 days at room temperature. The absolute configurations of the major isomers of the dihydropyrans 16-18, 20 and 21 were established by oxydative degradation to optically active alpha-phenylsuccinic acid derivatives.
• A New Synthetic Approach Toward (+)-Ambruticin Analogs: Preparation of a C10–C11cis-Isomer Fragment
  作者：Véronique Michelet、Kouacou Adiey、Bruno Bulic、Jean-Pierre Genêt、Gilles Dujardin、Sandrine Rossignol、Eric Brown、Loïc Toupet

  DOI：10.1002/(sici)1099-0690(199911)1999:11<2885::aid-ejoc2885>3.0.co;2-j

  日期：1999.11