3-oxo-7-octenoic acid | 191285-65-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 3-oxo-7-octenoic acid
• 英文别名: 3-oxooct-7-enoic acid
• CAS: 191285-65-1
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: HAEDVWDLPJAFDH-UHFFFAOYSA-N

物化性质

• 沸点：
  283.7±33.0 °C(Predicted)
• 密度：
  1.059±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-oxo-7-octenoic acid 在 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 (1R,4R,5S,7R,8S)-4,7-dihydroxy-7-pent-4-enyl-2,6,10-trioxatricyclo[6.3.0.01,5]undecan-9-one
  参考文献：
  名称：

  Concise Syntheses of (−)- and (+)-Syringolide 1 and (−)-Δ⁷-Syringolide 1

  摘要：

  (-)-和(+)-松柏醇内酯1已从2,3-O-异丙叉基-β-赤-五碳糖醛酸(1)中合成，而1则分别由D-或L-木糖简便制得。1与3-氧基辛酸进行缩合，随后将酯与TFA:H2O（9:1）处理，得到松柏醇内酯1，两步收率为6.3%。按照相同的合成路线，用3-氧基-7-辛烯酸替代3-氧基辛酸，得到了(-)-Δ(7)-松柏醇内酯1，收率为5.8%。还制备了阿拉伯糖和果糖的初级P-酮酸酯，以测试生物模拟环化反应生成松柏醇内酯类似物的选择性。

  DOI：

  10.1021/jo970461b
• 作为产物：
  描述：

  tert-butyl 3-oxooct-7-enoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 3-oxo-7-octenoic acid
  参考文献：
  名称：

  Synthesis of Pseudomonas quorum-sensing autoinducer analogs and structural entities required for induction of apoptosis in macrophages

  摘要：

  The synthesis of the analogs of N-3-oxododecanoyl-L-homoserine lactone (1) and their structure-activity relationship for the apoptotic induction in macrophages, P388D1 cells, are described. It was revealed that the position of the oxo group in the acyl side chain in addition to the presence of the L-homoserine lactone unit is crucial for the apoptosis-inducing activity. Furthermore, the long acyl side chains with hydrophobic distal ends are preferable for the activity. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.054

文献信息

• US4841043A
  申请人：——

  公开号：US4841043A

  公开（公告）日：1989-06-20
• Synthesis of Pseudomonas quorum-sensing autoinducer analogs and structural entities required for induction of apoptosis in macrophages
  作者：Manabu Horikawa、Kazuhiro Tateda、Etsu Tuzuki、Yoshikazu Ishii、Chihiro Ueda、Tohru Takabatake、Shinichi Miyairi、Keizou Yamaguchi、Masaji Ishiguro

  DOI：10.1016/j.bmcl.2006.01.054

  日期：2006.4

  The synthesis of the analogs of N-3-oxododecanoyl-L-homoserine lactone (1) and their structure-activity relationship for the apoptotic induction in macrophages, P388D1 cells, are described. It was revealed that the position of the oxo group in the acyl side chain in addition to the presence of the L-homoserine lactone unit is crucial for the apoptosis-inducing activity. Furthermore, the long acyl side chains with hydrophobic distal ends are preferable for the activity. (C) 2006 Elsevier Ltd. All rights reserved.
• Concise Syntheses of (−)- and (+)-Syringolide 1 and (−)-Δ⁷-Syringolide 1
  作者：Chun-min Zeng、Sharon L. Midland、Noel T. Keen、James J. Sims

  DOI：10.1021/jo970461b

  日期：1997.7.1

  (-)- and (+)-Syringolide 1 have been synthesized from 2,3-O-isopropylidene-beta-threo-pentulofuranose (1), which was readily prepared from D- or L-xylose, respectively. Condensation of 1 with 3-oxooctanoic acid and treatment of the ester with TFA:H2O (9:1) produced syringolide 1 in 6.3% yield for the two steps. According to the same synthetic route by replacing 3-oxooctanoic acid with 3-oxo-7-octenoic acid, (-)-Delta(7)-syringolide 1 was prepared in 5.8% yield. Primary P-keto esters of arabinulose and fructose were also prepared to test the selectivity of the biomimetic cyclization to form syringolide analogs.

  (-)-和(+)-松柏醇内酯1已从2,3-O-异丙叉基-β-赤-五碳糖醛酸(1)中合成，而1则分别由D-或L-木糖简便制得。1与3-氧基辛酸进行缩合，随后将酯与TFA:H2O（9:1）处理，得到松柏醇内酯1，两步收率为6.3%。按照相同的合成路线，用3-氧基-7-辛烯酸替代3-氧基辛酸，得到了(-)-Δ(7)-松柏醇内酯1，收率为5.8%。还制备了阿拉伯糖和果糖的初级P-酮酸酯，以测试生物模拟环化反应生成松柏醇内酯类似物的选择性。