(E)-(2R,3R)-methyl 3-(dimethylphenylsilyl)-2-methoxyhex-4-enoate | 134333-48-5

• 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)-(2R,3R)-methyl 3-(dimethylphenylsilyl)-2-methoxyhex-4-enoate
• 英文别名: methyl (E,2R,3R)-3-[dimethyl(phenyl)silyl]-2-methoxyhex-4-enoate
• CAS: 134333-48-5
• 化学式: C₁₆H₂₄O₃Si
• 分子量: 292.45
• InChiKey: QRWOBOBPYKWSCU-PHGPQXGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  20
• 可旋转键数：
  7
• 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：

  (E)-(2R,3R)-methyl 3-(dimethylphenylsilyl)-2-methoxyhex-4-enoate 在 nitronium tetrafluoborate 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 (E)-(2S,5S)-2-Methoxy-5-nitro-hex-3-enoic acid methyl ester
  参考文献：
  名称：

  通过巴豆基硅烷加成反应构建不对称 C-N 键：二肽等排体的立体控制途径

  摘要：

  描述了一种不对称合成 (E)-烯烃二肽等排体的新方法，其基于由四氟硼酸硝 (NO2BF4) 促进的手性 (E)-巴豆基硅烷和铜 (I)-手性 (E)-巴豆基硅烷的催化对映选择性氮丙啶化反应。硅烷试剂对氮基亲电试剂进行有效的抗 SE' 加成，得到 >96% de 的 (E)-烯烃等排体。拓扑偏差主要由硅烷试剂的面偏差控制。通过几种相关的巴豆基硅烷衍生物探索了该方法的范围。(E)-烯烃等排体是生物活性肽中肽键的不可水解的刚性类似物。

  DOI：

  10.1021/ja964364w

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。
• 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.
• Conjugate addition reactions of chiral (E)-crotylsilanes: application to an asymmetric [3 + 2] cyclopentane annulation
  作者：James S. Panek、Nareshkumar F. Jain

  DOI：10.1021/jo00061a001

  日期：1993.4

  Functionalized (E)-crotylsilanes 1 undergo Lewis acid promoted conjugate addition reactions with alpha-substituted enals and methyl vinyl ketone 2 to produce tetrasubstituted cyclopentanes 3 with high levels of diastereoselection. The reaction is believed to proceed by an initial 1,4-addition which is followed by a 1,2-silyl migration and a final cyclization step involving the derived boron enolate resulting in the construction of the cyclopentanoid product.
• Diastereoselective additions of chiral (E)-crotylsilanes to .alpha.-alkoxy and .beta.-alkoxy aldehydes. A one-step, silicon-directed tetrahydrofuran synthesis
  作者：James S. Panek、Michael Yang

  DOI：10.1021/ja00026a033

  日期：1991.12