(E)-(2S,3R)-Methyl 2-methyl-3-(dimethylphenylsilyl)hex-4-enoate | 134451-72-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-(2S,3R)-Methyl 2-methyl-3-(dimethylphenylsilyl)hex-4-enoate
• 英文别名: methyl (E,2S,3R)-3-[dimethyl(phenyl)silyl]-2-methylhex-4-enoate
• CAS: 134451-72-2
• 化学式: C₁₆H₂₄O₂Si
• 分子量: 276.451
• InChiKey: XKBCONIWGBBZCW-HEESEWQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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)-(2S,3R)-Methyl 2-methyl-3-(dimethylphenylsilyl)hex-4-enoate 在 nitrosonium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (R)-2-((S)-3-Methyl-4,5-dihydro-isoxazol-5-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Panek, James S.; Beresis, Richard T., Journal of the American Chemical Society, 1993, vol. 115, # 17, p. 7898 - 7899

  摘要：

  DOI：
• 作为产物：
  描述：

  4-己烯酸,3-(二甲基苯基甲硅烷基)-,甲基酯,(3S,4E)- 、 碘甲烷 在 正丁基锂 、 二异丙胺 作用下， 生成 (E)-(2R,3R)-Methyl 2-methyl-3-(dimethylphenylsilyl)hex-4-enoate 、 (E)-(2S,3R)-Methyl 2-methyl-3-(dimethylphenylsilyl)hex-4-enoate
  参考文献：
  名称：

  Diastereoselective electrophilic addition reactions to chiral .beta.-dimethylphenylsilyl ester enolates. Synthesis of 2,3-anti-.alpha.-substituted-.beta.-silyl-(E)-hex-4-enoates

  摘要：

  DOI：

  10.1021/jo00026a030

文献信息

• Diastereoselectivity in cyclopropanation and epoxidation reactions of chiral (E)-crotylsilanes: Asymmetric synthesis of substituted tetrahydrofurans
  作者：James S. Panek、Robert M. Garbaccio、Nareshkumar F. Jain

  DOI：10.1016/s0040-4039(00)78244-x

  日期：1994.8

  Functionalized (E)-crotylsilanes 1 bearing a bis-homoallylic hydroxyl group undergo diastereoselective cyclopropanation and epoxidation reactions to produce substituted tetrahydrofurans 3 and 5 respectively after an acid catalyzed heterocyclization.

  带有双-均烯丙基羟基的官能化的（E）-巴豆基硅烷1在酸催化的杂环化反应之后，进行非对映选择性的环丙烷化和环氧化反应，分别生成取代的四氢呋喃3和5。
• Lewis Acid-Mediated Carbocyclization Reactions of Chiral (<i>E</i>)-Crotylsilanes
  作者：Craig E. Masse、Les A. Dakin、Bradford S. Knight、James S. Panek

  DOI：10.1021/jo970832o

  日期：1997.12.1
• Panek, James S.; Yang, Michael, Journal of the American Chemical Society, 1991, vol. 113, # 17, p. 6594 - 6600
  作者：Panek, James S.、Yang, Michael

  DOI：——

  日期：——
• Remote asymmetric induction in diastereoface selective addition reactions of optically active .alpha.-substituted-.beta.-silyl (E)-hexenoates with achiral .alpha.-alkoxy and .beta.-alkoxy acetals
  作者：James S. Panek、Michael Yang

  DOI：10.1021/jo00020a009

  日期：1991.9

  Optically active and diastereomerically pure (E)-crotylsilanes 1 function as effective chiral carbon nucleophiles in trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed asymmetric addition reactions of achiral, alpha-alkoxy and beta-alkoxy acetals 2, resulting in the highly diastereo- and enantioselective construction of homoallylic ethers with excellent levels of 1,4- and 1,5-asymmetric induction.
• Double stereodifferentiation in the Lewis acid-promoted addition of chiral (E)-crotylsilanes with (S)-2-(benzyloxy)propanal. Effect of Lewis acid on reaction diastereoselection
  作者：James S. Panek、Richard Beresis

  DOI：10.1021/jo00056a005

  日期：1993.2

  Methyl alpha-methyl-beta-(dimethylphenylsilyl)-(E)-hex-4-enoates (28,3R)-1a undergo BF3.OEt2-Promoted additions with (S)-2-(benzyloxy)propanal (2) producing nearly enantiomerically pure cis-2,5-substituted tetrahydrofurans 3 whereas the reactions run under chelation controlled conditions employing SnCl4 resulted in the formation of the complementary trans-2,5-disubstituted tetrahydrofuran. Additions to the enantiomeric silane (2R,3S)-1b utilizing BF3.OEt2 or SnCl4 afforded the cis-2,5-disubstituted furan stereochemistry in both cases.