ethyl (R)-E-4-benzyloxy-5-methyl-hex-2-eneoate | 159383-92-3

• 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: ethyl (R)-E-4-benzyloxy-5-methyl-hex-2-eneoate
• 英文别名: ethyl (E,4R)-5-methyl-4-phenylmethoxyhex-2-enoate
• CAS: 159383-92-3
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: ZJMNEDSEARKVDO-NKSUMMKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  、 ethyl (R)-E-4-benzyloxy-5-methyl-hex-2-eneoate 在 Dimethylzinc 、 dilithium dimethylcyanocuprate 作用下， 生成 (R)-4-Benzyloxy-3-[bis-(2,4,6-trimethyl-phenyl)-silanyl]-5-methyl-hexanoic acid ethyl ester
  参考文献：
  名称：

  1-Oxa-2,2-(二甲苯基)硅杂环戊烷缩醛在多元醇立体选择性合成中的应用

  摘要：

  我们已经开发了一种立体选择性合成 1-oxa-2,2-（二甲苯基）硅杂环戊烷缩醛的路线，该缩醛是合成高度官能化的 1,3-二醇的中间体。该路线涉及氢化硅烷基阴离子的非对映选择性共轭加成反应、随后的非对映选择性烯醇化物烷基化和氟化物催化的分子内氢化硅烷化反应以提供氧硅杂环戊烷缩醛。高度选择性的亲核取代反应，然后氧化 C-Si 键，生成所需的多元醇。

  DOI：

  10.1021/ja027335w
• 作为产物：
  描述：

  ((E)-(R)-1-Isopropyl-hept-2-enyloxymethyl)-benzene 在 二甲基硫 、 臭氧 作用下， 生成 ethyl (R)-E-4-benzyloxy-5-methyl-hex-2-eneoate
  参考文献：
  名称：

  Steric and Electronic Effects in Conformational Preferences of C1-Oxygenated Chiral Alkenes

  摘要：

  A variable temperature NMR study shows that the benzyl protective group on the hydroxy function of a chiral allylic alcohol enhances the CH eclipsed form (I). On the other hand, various silyl ethers enhance the preference for the CO eclipsed conformer. However, when both the allylic R group and the hydroxy protective group are bulky (R tert-butyl, P = TIPS), the staggered conformation of the chiral alkene becomes preferred. An acetate group does not have an apparent effect on the conformational preference of the protected allylic alcohol. These facts are explained in terms of steric and electronic interactions.

  DOI：

  10.1021/jo00112a012

文献信息

• Utilization of 1-Oxa-2,2-(dimesityl)silacyclopentane Acetals in the Stereoselective Synthesis of Polyols
  作者：Sharon A. Powell、Jason M. Tenenbaum、K. A. Woerpel

  DOI：10.1021/ja027335w

  日期：2002.10.1

  developed a route for the stereoselective synthesis of 1-oxa-2,2-(dimesityl)silacyclopentane acetals, intermediates in the synthesis of highly functionalized 1,3-diols. This route involves a diastereoselective conjugate addition reaction of a hydrosilyl anion, a subsequent diastereoselective enolate alkylation, and a fluoride-catalyzed intramolecular hydrosilylation reaction to afford the oxasilacyclopentane

  我们已经开发了一种立体选择性合成 1-oxa-2,2-（二甲苯基）硅杂环戊烷缩醛的路线，该缩醛是合成高度官能化的 1,3-二醇的中间体。该路线涉及氢化硅烷基阴离子的非对映选择性共轭加成反应、随后的非对映选择性烯醇化物烷基化和氟化物催化的分子内氢化硅烷化反应以提供氧硅杂环戊烷缩醛。高度选择性的亲核取代反应，然后氧化 C-Si 键，生成所需的多元醇。
• Steric and Electronic Effects in Conformational Preferences of C1-Oxygenated Chiral Alkenes
  作者：Benjamin W. Gung、Jason P. Melnick、Mark A. Wolf、Amanda King

  DOI：10.1021/jo00112a012

  日期：1995.4

  A variable temperature NMR study shows that the benzyl protective group on the hydroxy function of a chiral allylic alcohol enhances the CH eclipsed form (I). On the other hand, various silyl ethers enhance the preference for the CO eclipsed conformer. However, when both the allylic R group and the hydroxy protective group are bulky (R tert-butyl, P = TIPS), the staggered conformation of the chiral alkene becomes preferred. An acetate group does not have an apparent effect on the conformational preference of the protected allylic alcohol. These facts are explained in terms of steric and electronic interactions.