(1R,4R,5S,7R,8S)-4-hydroxy-7-pentyl-7-phenylmethoxy-2,6,10-trioxatricyclo[6.3.0.01,5]undecan-9-one | 186265-00-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: (1R,4R,5S,7R,8S)-4-hydroxy-7-pentyl-7-phenylmethoxy-2,6,10-trioxatricyclo[6.3.0.01,5]undecan-9-one
• CAS: 186265-00-9
• 化学式: C₂₀H₂₆O₆
• 分子量: 362.423
• InChiKey: KURYQYWEZXOLOO-QBYKVAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,4R,5S,7R,8S)-4-hydroxy-7-pentyl-7-phenylmethoxy-2,6,10-trioxatricyclo[6.3.0.01,5]undecan-9-one 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 二甲基氨基丙基乙基碳酰胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 19.0h， 生成 [(1R,4R,5S,7R,8S)-7-hydroxy-9-oxo-7-pentyl-2,6,10-trioxatricyclo[6.3.0.01,5]undecan-4-yl] 2-(3,4,5-trimethoxyphenyl)acetate
  参考文献：
  名称：

  Synthesis of syringolide 1 ketals and esters for receptor studies

  摘要：

  The syringolides, specified by avirulence gene D from Pseudomonas syringae, elicit a disease defense reaction only in soybean cultivars carrying the Rpg4 disease resistance gene. In order to identify structural features important for elicitor activity and construct highly labelled elicitor-active probes, several syringolide esters and ketals were synthesized. Alteration of the C-3 hemiketal group of syringolide 1 abolished elicitor activity, but ester derivatives based on the C-4' hydroxy group all retained activity. [I-125]4'-(2-iodo-3,4,5-trimethoxyphenylacetyl) syringolide 1 was prepared for receptor studies. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0031-9422(96)00530-4
• 作为产物：
  描述：

  syringolide 1 、 苯甲醇 在 Dowex 50W-X₈*HCl 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到(1R,4R,5S,7R,8S)-4-hydroxy-7-pentyl-7-phenylmethoxy-2,6,10-trioxatricyclo[6.3.0.01,5]undecan-9-one
  参考文献：
  名称：

  Synthesis of syringolide 1 ketals and esters for receptor studies

  摘要：

  The syringolides, specified by avirulence gene D from Pseudomonas syringae, elicit a disease defense reaction only in soybean cultivars carrying the Rpg4 disease resistance gene. In order to identify structural features important for elicitor activity and construct highly labelled elicitor-active probes, several syringolide esters and ketals were synthesized. Alteration of the C-3 hemiketal group of syringolide 1 abolished elicitor activity, but ester derivatives based on the C-4' hydroxy group all retained activity. [I-125]4'-(2-iodo-3,4,5-trimethoxyphenylacetyl) syringolide 1 was prepared for receptor studies. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0031-9422(96)00530-4

文献信息

• Synthesis of syringolide 1 ketals and esters for receptor studies
  作者：Tetsu Tsurushima、Sharon L. Midland、Chun-min Zeng、Cheng Ji、James J. Sims、Noel T. Keen

  DOI：10.1016/s0031-9422(96)00530-4

  日期：1996.12

  The syringolides, specified by avirulence gene D from Pseudomonas syringae, elicit a disease defense reaction only in soybean cultivars carrying the Rpg4 disease resistance gene. In order to identify structural features important for elicitor activity and construct highly labelled elicitor-active probes, several syringolide esters and ketals were synthesized. Alteration of the C-3 hemiketal group of syringolide 1 abolished elicitor activity, but ester derivatives based on the C-4' hydroxy group all retained activity. [I-125]4'-(2-iodo-3,4,5-trimethoxyphenylacetyl) syringolide 1 was prepared for receptor studies. Copyright (C) 1996 Elsevier Science Ltd