ethyl (2Z)-2-(1-hydroxy-1-phenylmethyl)-3-phenylacrylate | 210752-49-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: ethyl (2Z)-2-(1-hydroxy-1-phenylmethyl)-3-phenylacrylate
• 英文别名: ethyl (Z)-2-(hydroxyl(phenyl)methyl)-3-phenylacrylate；(Z)-ethyl 2-(hydroxy(phenyl)methyl)-3-phenylacrylate；(Z)-ethyl 2-[hydroxy(phenyl)methyl]-3-phenylacrylate；2-(α-hydroxy-benzyl)-3-phenyl-acrylic acid ethyl ester；2-(α-Hydroxy-benzyl)-3-phenyl-acrylsaeure-aethylester；ethyl (Z)-2-[hydroxy(phenyl)methyl]-3-phenylprop-2-enoate
• CAS: 210752-49-1
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: LJXIUDZTIJVURM-SSZFMOIBSA-N

物化性质

• 沸点：
  453.6±45.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (2Z)-2-(1-hydroxy-1-phenylmethyl)-3-phenylacrylate 在 对甲苯磺酸 、 甲苯 作用下， 生成 ethyl 3-phenyl-1H-indene-2-carboxylate
  参考文献：
  名称：

  Postma; Arens, Recueil des Travaux Chimiques des Pays-Bas, 1956, vol. 75, p. 1385,1396

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲醛 在 palladium diacetate 、 sodium carbonate 、 magnesium iodide 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 生成 ethyl (2Z)-2-(1-hydroxy-1-phenylmethyl)-3-phenylacrylate
  参考文献：
  名称：

  酯代醇-克莱森重排路线取代4-亚烷基脯氨酸。对Lucentamycin A的确定性结构修订的研究

  摘要：

  取代的4-亚烷基萘脯氨酸代表一类罕见的天然氨基酸，具有有前途的生物活性。Lucentamycin A是一种细胞毒性的海洋衍生三肽，带有一个在已知肽天然产物中独有的4-乙基--3-甲基脯氨酸（Emp）残基。在本文中，我们使用通用的酯烯酸酯-克莱森重排研究了Emp及其相关的4-亚烷基脯氨酸的合成。用许多不同取代的甘氨酸酯底物描述了键重排反应的范围和选择性。在环境温度下用过量的NaHMDS处理烯丙基酯会产生高度取代的α-烯丙基甘氨酸产物，具有良好或优异的非对映选择性。二肽非对映异构体的拆分和环化形成吡咯烷环提供了快速进入立体纯脯氨酰二肽的途径。我们已将这种策略应用于荧光素霉素A的四个含Emp异构体的合成，以期对天然产物进行确定的立体化学修饰。我们的研究表明，Emp立体生成中心不是结构错误分配的根源。当前的策略应该在合成其他天然产物类似物和相关的3-烷基-4-亚烷基脯氨酸中找到广泛的用途。

  DOI：

  10.1021/jo201727g

文献信息

• Synthesis of β- and β,β-substituted Morita–Baylis–Hillman adducts using a two-step protocol
  作者：David I. Magee、Same Ratshonka、Jessica McConaghy、Maggie Hood

  DOI：10.1139/v2012-017

  日期：2012.5

  The synthesis of a large number of β- and β,β-substituted keto esters was successful by the use of the Knoevenagel condensation reaction. The stereoselectivity of these reactions was improved by alteration of various substituent groups. Although there were few examples of complete Z selectivity, the use of tert-butyl acetoacetate with either aromatic or aliphatic aldehydes afforded Z selectivity. The selective reductions of these substituted keto esters was successfully achieved by using a combination of NaBH₄ and CeCl₃·7H₂O or Yb(OTf)₃, which allowed a facile synthesis of a large number of stereochemically pure substituted Morita–Baylis–Hillman adducts, including β,β-substituted adducts.

  大量β-和β,β-取代酮酯的合成成功地通过Knoevenagel缩合反应实现。通过改变各种取代基团来改善这些反应的立体选择性。尽管完全Z选择性的例子很少，但是使用叔丁基乙酰乙酸酯与芳香族或脂肪族醛可以获得Z选择性。这些取代酮酯的选择性还原成功地通过使用NaBH₄和CeCl₃·7H₂O或Yb(OTf)₃的组合实现，从而实现了大量立体化纯净的取代Morita–Baylis–Hillman加合物的简便合成，包括β,β-取代加合物。
• A new stereospecific synthesis of unusual (Z)-β-branched Baylis-Hillman adducts
  作者：Guigen Li、Han-Xun Wei、Steven Willis

  DOI：10.1016/s0040-4039(98)00850-8

  日期：1998.6

  A new method has been developed for the stereospecific synthesis of unusual (Z)-β-branched Baylis-Hillman adducts with high selectivity (>99 %) in modest to good yields. The process involves successful formation of anionic β-substituted [α-(alkoxycarbonyl)vinyl]aluminum intermediates and their coupling with aldehydes and ketones catalyzed by n-Bu2BOTf at −78 °C.

  已开发出一种新方法，以中等收率到良好收率，以高选择性（> 99％）立体合成不寻常的（Z）-β-支链Baylis-Hillman加合物。该方法涉及β阴离子取代[α-（烷氧基羰基）乙烯基]铝中间体的成功形成以及它们与催化醛和酮耦合Ñ -Bu 2在-78℃下BOTf。
• The first successful intermolecular Heck reaction of Baylis–Hillman adducts: synthesis of β-aryl substituted Baylis–Hillman adducts
  作者：Jeong Mi Kim、Ko Hoon Kim、Taek Hyeon Kim、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2008.03.102

  日期：2008.5

  The first successful intermolecular Heck reaction between Baylis–Hillman adducts and aryl iodides was achieved under the conditions comprising Pd(OAc)2/n-Bu4NBr/KOAc in CH3CN.

  在包括CH 3 CN中的Pd（OAc）2 / n -Bu 4 NBr / KOAc的条件下，成功实现了Baylis-Hillman加合物和碘代芳基化合物之间的第一个成功的分子间Heck反应。
• Novel cross-coupling reactions between organotellurides and Grignard reagents employing a MnCl2/CuI catalytic system
  作者：Marcio S. Silva、Renan S. Ferrarini、Bruno A. Sousa、Fabiano T. Toledo、João V. Comasseto、Rogério A. Gariani

  DOI：10.1016/j.tetlet.2012.04.134

  日期：2012.7

  We present a general protocol for the cross-coupling reaction of Grignard reagents and organic tellurides. Aryl Grignard reagents react stereospecifically with vinyl tellurides in the presence of a catalytic amount of manganese (II) chloride and copper (I) iodide to produce good yields of the corresponding cross-coupling products.

  我们提出了格氏试剂和有机碲化物交叉偶联反应的一般方案。在催化量的氯化锰（II）和碘化铜（I）的存在下，芳基格氏试剂与碲化乙烯立体定向反应，从而产生相应交叉偶联产物的良好收率。
• 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.