2-((1S,2S,3R)-3-((triethylsilyl)oxy)-2-((Z)-pent-2-en-1-yl)cyclopentyl)acetic acid | 1093971-90-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-((1S,2S,3R)-3-((triethylsilyl)oxy)-2-((Z)-pent-2-en-1-yl)cyclopentyl)acetic acid
• CAS: 1093971-90-4
• 化学式: C₁₈H₃₄O₃Si
• 分子量: 326.552
• InChiKey: SFQYTMWJILBKSP-FQDGRLNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  22.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-((1S,2S,3R)-3-((triethylsilyl)oxy)-2-((Z)-pent-2-en-1-yl)cyclopentyl)acetic acid 、 氯甲酸异丁酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Strategy for synthesis of the isoleucine conjugate of epi-jasmonic acid

  摘要：

  The TES ether of 2-((1R,2S,3R)-3-hydroxy-2-((Z)-pent-2-enyl)cyclopentyl)acetic acid (5, equal to the reduction product of epi-jasmonic acid) derived from (1R,4S)-4-hydroxycyclopent-2-enyl acetate (19) in 13 steps was activated by using isobutyl chloroformate and was subjected to condensation with isoleucine at room temperature for 48 h. The product was desilylated and oxidized to the isoleucine conjugate of epi-jasmonic acid in 68% yield over three steps. Similarly, allo-isoleucine conjugate of epi-jasmonic acid and three isoleucine conjugates of ent-epi-jasmonic acid, jasmonic acid, and ent-jasmonic acid were synthesized. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.144
• 作为产物：
  描述：

  2-[(1S,2S,3R)-3-hydroxy-2-[(Z)-pent-2-enyl]cyclopentyl]acetic acid 在 咪唑 、 三乙基氯硅烷 作用下， 生成 2-((1S,2S,3R)-3-((triethylsilyl)oxy)-2-((Z)-pent-2-en-1-yl)cyclopentyl)acetic acid
  参考文献：
  名称：

  Strategy for synthesis of the isoleucine conjugate of epi-jasmonic acid

  摘要：

  The TES ether of 2-((1R,2S,3R)-3-hydroxy-2-((Z)-pent-2-enyl)cyclopentyl)acetic acid (5, equal to the reduction product of epi-jasmonic acid) derived from (1R,4S)-4-hydroxycyclopent-2-enyl acetate (19) in 13 steps was activated by using isobutyl chloroformate and was subjected to condensation with isoleucine at room temperature for 48 h. The product was desilylated and oxidized to the isoleucine conjugate of epi-jasmonic acid in 68% yield over three steps. Similarly, allo-isoleucine conjugate of epi-jasmonic acid and three isoleucine conjugates of ent-epi-jasmonic acid, jasmonic acid, and ent-jasmonic acid were synthesized. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.144

文献信息

• Synthesis of the amino acid conjugates of epi-jasmonic acid
  作者：N. Ogawa、Y. Kobayashi

  DOI：10.1007/s00726-011-0925-z

  日期：2012.5

  The TES ether of the C6-hydroxy derivative of naturally occurring epi-jasmonic acid (epi-JA) was designed as epimerization-free equivalent of epi-JA. The TES ether was synthesized from (1R,4S)-4-hydroxycyclopent-2-enyl acetate in 13 steps. The acid part of the ether was activated with ClCO2Bui and subjected to condensation with l-amino acid at room temperature for 48 h. The TES group in the condensation

  的TES醚的天然存在的C6羟基衍生物的外延-jasmonic酸（EPI -ja）被设计为自由差向异构当量的外延-ja。由（1 R，4 S）-4-羟基环戊-2-烯基乙酸酯经13个步骤合成TES醚。醚的酸部分用ClCO激活2卜我并进行缩合升-氨基在室温下酸48小时。在HCO 2 H中（0°C，30分钟）除去缩合产物中的TES基团，然后用Jones试剂（丙酮，0°C，30分钟）氧化所得的羟基，以提供EPI的氨基酸缀合物。-JA 所检查的氨基酸为1-异亮氨酸，1-亮氨酸，1-丙氨酸，1-缬氨酸和d -allo-异亮氨酸，与反式异构体相比，其缀合物的收率为48-68％，非对映异构体纯度为89-96％。类似地，将ePI -JA的可能的三种立体异构体与1-异亮氨酸成功缩合，以高收率产生相应的立体异构体。