ethyl (Z,4R,5S)-4,5-isopropylidenedioxyhepta-2,6-dienoate | 329014-23-5

• 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: ethyl (Z,4R,5S)-4,5-isopropylidenedioxyhepta-2,6-dienoate
• 英文别名: ethyl (4S,5R)-(Z)-4,5-isopropylidenedioxyhepta-2,6-dienoate；ethyl (Z)-3-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate
• CAS: 329014-23-5
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: FPOGIKDEANACIF-ZTXJHGQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (Z,4R,5S)-4,5-isopropylidenedioxyhepta-2,6-dienoate 在 四丁基氟化铵 、 异氰酸苯酯 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 99.0h， 生成 (3aR,4R,5S,6S)-6-ethoxycarbonylmethyl-4,5-isopropylidenedioxy-3a,4,5,6-tetrahydro-3H-cyclopent[c]isoxazole
  参考文献：
  名称：

  Diastereocontrol in the intramolecular cycloadditions of 2-substituted-erythro-3,4-isopropylidenedioxyhex-5-enenitrile oxides

  摘要：

  The influence of the 2-substituent on the diastereoselectivity of the intramolecular cycloadditions in a series of 2-substitute-erythro-3,4-isopropylidene-dioxyhex-5-enenitrile oxides, generated in situ from Selected sugar derivatives, was examined. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00991-6
• 作为产物：
  描述：

  methyl 5-deoxy-5-iodo-2,3-isopropylidene-β-D-ribofuranoside 在 苯甲酸 、 锌 作用下， 以 乙醇 为溶剂， 反应 28.0h， 生成 ethyl (Z,4R,5S)-4,5-isopropylidenedioxyhepta-2,6-dienoate
  参考文献：
  名称：

  Diastereocontrol in the intramolecular cycloadditions of 2-substituted-erythro-3,4-isopropylidenedioxyhex-5-enenitrile oxides

  摘要：

  The influence of the 2-substituent on the diastereoselectivity of the intramolecular cycloadditions in a series of 2-substitute-erythro-3,4-isopropylidene-dioxyhex-5-enenitrile oxides, generated in situ from Selected sugar derivatives, was examined. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00991-6

文献信息

• Facile Synthesis of Enantiomerically Pure Carbafuranoses: Precursors of Carbocyclic Nucleosides
  作者：John K. Gallos、Constantinos C. Dellios、Ekaterini E. Spata

  DOI：10.1002/1099-0690(200101)2001:1<79::aid-ejoc79>3.0.co;2-1

  日期：2001.1

  An efficient and highly diastereoselective synthetic approach to enantiomerically pure (−)-(1R,2R,3S,4R)- and (+)-(1S,2S,3R,4S)-4-hydroxyethylcyclopentane-1,2,3-triols is reported, which involves conversion of D-ribose or D-arabinose to (+)- or (−)-ethyl Z-4,5-isopropylidenedioxyhepta-2,6-dienoate, mercuration of the terminal double bond by mercury(II) acetate, followed by reductive radical cyclization

  一种对映异构纯 (-)-(1R,2R,3S,4R)- 和 (+)-(1S,2S,3R,4S)-4-羟乙基环戊烷-1,2,3-三醇的高效且高度非对映选择性合成方法据报道，这涉及将 D-核糖或 D-阿拉伯糖转化为 (+)- 或 (-)-乙基 Z-4,5-isopropylidenedioxyhepta-2,6-dienoate，通过汞 (II) 对末端双键进行汞化乙酸盐，然后进行还原自由基环化和进一步的标准还原和脱保护操作。
• Diastereocontrol in the intramolecular cycloadditions of 2-substituted-erythro-3,4-isopropylidenedioxyhex-5-enenitrile oxides
  作者：John K. Gallos、Alexandros E. Koumbis、Vassiliki P. Xiraphaki、Constantinos C. Dellios、Evdoxia Coutouli-Argyropoulou

  DOI：10.1016/s0040-4020(99)00991-6

  日期：1999.12

  The influence of the 2-substituent on the diastereoselectivity of the intramolecular cycloadditions in a series of 2-substitute-erythro-3,4-isopropylidene-dioxyhex-5-enenitrile oxides, generated in situ from Selected sugar derivatives, was examined. (C) 1999 Elsevier Science Ltd. All rights reserved.