ethyl-(E)-(2SR,5RS)-6-benzyloxy-5-hydroxy-2-methyl-3-hexenoate

• 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-(E)-(2SR,5RS)-6-benzyloxy-5-hydroxy-2-methyl-3-hexenoate
• 英文别名: ethyl (E)-(2RS,5SR)-6-benzyloxy-5-hydroxy-2-methyl-3-hexenoate；ethyl (E,2S,5R)-5-hydroxy-2-methyl-6-phenylmethoxyhex-3-enoate
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: JQPDLIPSYMWHCO-BPKFXHHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl-(E)-(2SR,5RS)-6-benzyloxy-5-hydroxy-2-methyl-3-hexenoate 在 palladium on activated charcoal 氢气 作用下， 生成 (2S,5R)-6-Benzyloxy-5-hydroxy-2-methyl-hexanoic acid ethyl ester
  参考文献：
  名称：

  A regio- and stereoselective α-methylation of γ,δ-epoxy-α,β-unsaturated esters with a Me₂Zn–CuCN reagent

  摘要：

  通过使用Me2Zn–CuCN试剂，实现了一种高度区域选择性和立体选择性的α-甲基化反应，涉及γ, δ-环氧-α, β-不饱和酯。

  DOI：

  10.1039/b205957f
• 作为产物：
  描述：

  (4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde 在 氯化亚砜 、 三氟化硼乙醚 、 甲基锂 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.33h， 生成 ethyl-(E)-(2SR,5RS)-6-benzyloxy-5-hydroxy-2-methyl-3-hexenoate
  参考文献：
  名称：

  Addition of organocopper reagents to cyclic sulfites or carbonates of γ,δ-dihydroxy (E)-α,β-enoates

  摘要：

  Reaction of cyclic sulfites or carbonates of gamma,delta-dihydroxy (E)-alpha,beta-enoates with R2Cu(CN)Li2, BF3; RCu(CN)Li, BF3 (R = Me-,n-Bu-)afforded either diastereoselective S(N)2' products or reductive elimination product depending on reaction conditions. Addition of R2Cu(CN)Li2, BF3 (R = Me-, n-Bu-) to cyclic sulfite (1) or cyclic carbonate (3) (inverse addition) afforded highly regio-, (E)-stereo- and diastereoselectively alpha-alkylation products (6 and 8). By using this methodology, (2S, 5S)-trans-2-methyl-5-hexanolide, the pheromone of the carpenter bee Xylocopa hirutissima was synthesized.

  DOI：

  10.1016/s0957-4166(00)80506-6

文献信息

• Stereoselective SN2′ alkylation reaction sequence of the γ,δ-epoxy α,β-unsaturated ester system via γ,δ-chlorohydrin intermediates by the use of a R3Al–CuCN reagent
  作者：Fumihiko Yoshimura、Atsushi Matsui、Atsushi Hirai、Keiji Tanino、Masaaki Miyashita

  DOI：10.1016/j.tetlet.2009.06.106

  日期：2009.9

  A novel stereoselective SN2′ alkylation reaction sequence of the γ,δ-epoxy α,β-unsaturated ester system has been developed which involves a regioselective substitution reaction with chloride ions at the γ-position and a subsequent SN2′ alkylation reaction of the resulting γ-chloro-δ-hydroxy derivatives with a R3Al–CuCN reagent. The new methodology was demonstrated to be applicable to a variety of substrates

  已经开发了γ，δ-环氧α，β-不饱和酯系统的新型立体选择性S N 2'烷基化反应序列，其涉及在γ-位与氯离子的区域选择性取代反应和随后的S N 2'烷基化反应R 3 Al–CuCN试剂合成的γ-氯代-δ-羟基衍生物。事实证明，该新方法可适用于多种底物，并提供各种δ-羟基-α-烷基-β，γ-不饱和酯，包括以高度立体选择性的方式在α-位带有季不对称碳原子的那些酯，以及高产。
• A regio- and stereoselective α-methylation of γ,δ-epoxy-α,β-unsaturated esters with a Me₂Zn–CuCN reagent
  作者：Atsushi Hirai、Atsushi Matsui、Kei Komatsu、Keiji Tanino、Masaaki Miyashita

  DOI：10.1039/b205957f

  日期：——

  A highly regio- and stereoselective α-methylation reaction of γ, δ-epoxy-α, β-unsaturated esters was achieved by using a Me2Zn–CuCN reagent.

  通过使用Me2Zn–CuCN试剂，实现了一种高度区域选择性和立体选择性的α-甲基化反应，涉及γ, δ-环氧-α, β-不饱和酯。
• Addition of organocopper reagents to cyclic sulfites or carbonates of γ,δ-dihydroxy (E)-α,β-enoates
  作者：Suk-Ku Kang、Young-Won Park、Dong-Ha Lee、Hyeong-Su Sim、Jae-Hoon Jeon

  DOI：10.1016/s0957-4166(00)80506-6

  日期：1992.6

  Reaction of cyclic sulfites or carbonates of gamma,delta-dihydroxy (E)-alpha,beta-enoates with R2Cu(CN)Li2, BF3; RCu(CN)Li, BF3 (R = Me-,n-Bu-)afforded either diastereoselective S(N)2' products or reductive elimination product depending on reaction conditions. Addition of R2Cu(CN)Li2, BF3 (R = Me-, n-Bu-) to cyclic sulfite (1) or cyclic carbonate (3) (inverse addition) afforded highly regio-, (E)-stereo- and diastereoselectively alpha-alkylation products (6 and 8). By using this methodology, (2S, 5S)-trans-2-methyl-5-hexanolide, the pheromone of the carpenter bee Xylocopa hirutissima was synthesized.