(E)-methyl cis-4,5-epoxy-6-(benzyloxy)-2-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: (E)-methyl cis-4,5-epoxy-6-(benzyloxy)-2-hexenoate
• 英文别名: methyl (E)-3-[(2R,3S)-3-(phenylmethoxymethyl)oxiran-2-yl]prop-2-enoate
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: QVYASHUDJVVNHB-NAISLTENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-methyl cis-4,5-epoxy-6-(benzyloxy)-2-hexenoate 在 sodium azide 、 氯化铵 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以85%的产率得到intermediate 14
  参考文献：
  名称：

  Friedel-Crafts Reactions of Vinylaziridine Linked to an Ester Group

  摘要：

  Intermolecular Friedel-Crafts reactions of vinylaziridines 11, 12, 15, 16 and 20 linked. to an ester with various benzene 'derivatives occurred at the C4 position selectively to afford 5-amino-4-aryl-2-hexenoate derivatives in good yields.

  DOI：

  10.3987/com-10-12115
• 作为产物：
  描述：

  ((2R,3S)-3-((benzyloxy)methyl)oxiran-2-yl)methanol 在 吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二甲基亚砜 为溶剂， 生成 (E)-methyl cis-4,5-epoxy-6-(benzyloxy)-2-hexenoate
  参考文献：
  名称：

  对映体选择性合成的四个异构体的组成部分，可用于合成2-nor-leukotriene类似物

  摘要：

  我们在这封信中报告了四个异构体官能化的环氧化物（3a，3b，3c和3d）的对映选择性合成，它们是合成2-nor-leukotriene类似物的有用组成部分。所有四种环氧化物均正式源自单一的非手性原料2-丁炔-1,4-二醇7。

  DOI：

  10.1016/s0957-4166(00)80273-6

文献信息

• Enantioselective synthesis of four isomeric building blocks useful in the synthesis of 2-nor-leukotriene analogues
  作者：F.D. Bellamy、M. Bondoux、B. Boubia、P. Dodey、C. Mioskowski

  DOI：10.1016/s0957-4166(00)80273-6

  日期：1992.1

  We report, in this letter, the enantioselective synthesis of four isomeric functionalized epoxides (3a, 3b, 3c and 3d) which are useful building blocks for the synthesis of 2-nor-leukotriene analogues. All four epoxides are formally derived from a single non chiral starting material, the 2-butyne-1,4-diol 7.

  我们在这封信中报告了四个异构体官能化的环氧化物（3a，3b，3c和3d）的对映选择性合成，它们是合成2-nor-leukotriene类似物的有用组成部分。所有四种环氧化物均正式源自单一的非手性原料2-丁炔-1,4-二醇7。
• Reductive cleavage reaction of .gamma.-functionalized .alpha.,.beta.-unsaturated esters and halomethyls mediated with magnesium in methanol
  作者：Chwang Siek Pak、Eun Lee、Ge Hyeong Lee

  DOI：10.1021/jo00058a038

  日期：1993.3

  Reductive cleavage of various types of C-O and C-N bonds tethered to alpha,beta-unsaturated esters and halomethyls was mediated with magnesium in methanol, which provided a facile method for the synthesis of delta-hydroxy or delta-amino beta,gamma-unsaturated esters and allylic alcohols. Regardless of the geometry (E or Z) of the alpha,beta-unsaturated esters, 1a-b, 5a-c, 11, 13, and 23, the cleavage product obtained was exclusively the E isomer of the corresponding deconjugated hydroxy and amino esters. The steric bias and ring strain of 15, 17, and 21 gave rise to a product mixture of E and Z isomers.
• Friedel-Crafts Reactions of Vinylaziridine Linked to an Ester Group
  作者：Shinji Nagumo、Hisashi Takada、Eiko Yasui、Yui Sahara、Yūki Chinen、Hirotoshi Tanaka、Yusuke Morita、Chihiro Kobiki、Daiki Narisawa、Megumi Mizukami、Masaaki Miyashita

  DOI：10.3987/com-10-12115

  日期：——

  Intermolecular Friedel-Crafts reactions of vinylaziridines 11, 12, 15, 16 and 20 linked. to an ester with various benzene 'derivatives occurred at the C4 position selectively to afford 5-amino-4-aryl-2-hexenoate derivatives in good yields.