N-[2-[(1R,2R,3S)-3-Hydroxy-2-(2Z)-2-penten-1-ylcyclopentyl]acetyl]-L-isoleucine | 162854-97-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[2-[(1R,2R,3S)-3-Hydroxy-2-(2Z)-2-penten-1-ylcyclopentyl]acetyl]-L-isoleucine
• 英文别名: (2S,3S)-2-[[2-[(1R,2R,3S)-3-hydroxy-2-[(Z)-pent-2-enyl]cyclopentyl]acetyl]amino]-3-methylpentanoic acid
• CAS: 162854-97-9
• 化学式: C₁₈H₃₁NO₄
• 分子量: 325.448
• InChiKey: SJUZAQZEDDCWNC-SFOIGYNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[2-[(1R,2R,3S)-3-Hydroxy-2-(2Z)-2-penten-1-ylcyclopentyl]acetyl]-L-isoleucine 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 以89%的产率得到(±)-茉莉酸-异亮氨酸
  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：

  在 甲酸 作用下， 生成 N-[2-[(1R,2R,3S)-3-Hydroxy-2-(2Z)-2-penten-1-ylcyclopentyl]acetyl]-L-isoleucine
  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

• Strategy for synthesis of the isoleucine conjugate of epi-jasmonic acid
  作者：Narihito Ogawa、Yuichi Kobayashi

  DOI：10.1016/j.tetlet.2008.09.144

  日期：2008.12

  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.