methyl (2E)-6-oxoundeca-2,10-dienoate | 319491-31-1

• 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: methyl (2E)-6-oxoundeca-2,10-dienoate
• 英文别名: Methyl 6-oxoundeca-1,9-dienoate
• CAS: 319491-31-1
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: SNXVUQRTTDHNSZ-JXMROGBWSA-N

物化性质

• 沸点：
  314.1±35.0 °C(Predicted)
• 密度：
  0.973±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2E)-6-oxoundeca-2,10-dienoate 在 9-硼双环[3.3.1]壬烷 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 以69%的产率得到
  参考文献：
  名称：

  Synthesis of a bioprobe for elucidation of target molecule of spongean anti-malarial peroxides

  摘要：

  The reactants of an anti-malarial peroxide having a 6-carbomethoxymethyl-3-methoxy-1,2-dioxane moiety treated with FeSO4 were analyzed. For mechanistic study of the anti-malarial peroxide, two biotinylated probes to elucidate the target molecules were designed and synthesized. The two synthesized probes showed potent anti-malarial activity, and one of them was proved to form an irreversible binding with protein in a model experiment. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.086
• 作为产物：
  描述：

  2-(4'-Methoxycarbonyl-3'-butenyl)-2-(4"-pentenyl)-1,3-dithiane 在 N-氯代丁二酰亚胺 、 silver nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.25h， 生成 methyl (2E)-6-oxoundeca-2,10-dienoate
  参考文献：
  名称：

  肟的串联分子内迈克尔加成和1，3-偶极环加成反应；通用的新型碳-碳键形成方法

  摘要：

  肟经过分子内迈克尔加成反应，形成邻近的负电性烯烃，生成环状硝酮，可被分子间和分子内捕获在分别或串联发生的1,3-偶极环加成反应中。

  DOI：

  10.1039/c39870001327

文献信息

• Tandem intramolecular Michael addition and 1,3-dipolar cycloaddition reactions of oximes; versatile new carbon–carbon bond forming methodology
  作者：Paul Armstrong、Ronald Grigg、Sivagnanasundram Surendrakumar、William J. Warnock

  DOI：10.1039/c39870001327

  日期：——

  Oximes undergo intramolecular Michael addition to proximate electronegative alkenes, generating cyclic nitrones which can be trapped inter- and intra-molecularly in 1,3-dipolar cycloaddition reactions taking place either separately or in tandem.

  肟经过分子内迈克尔加成反应，形成邻近的负电性烯烃，生成环状硝酮，可被分子间和分子内捕获在分别或串联发生的1,3-偶极环加成反应中。
• Application of the intramolecular azomethine imine cycloaddition to the construction of a novel, orthogonally protected spirodiamino acid scaffold
  作者：Roland E Dolle、Michael C Barden、Paul E Brennan、Gulzar Ahmed、Vinh Tran、Douglas M Ho

  DOI：10.1016/s0040-4039(99)00391-3

  日期：1999.4

  Hydrazone 4 undergoes tandem intramolecular Michael addition — intramolecular azomethine imine cycloaddition in ethanol at reflux to furnish the tricyclic pyrazoline methyl ester 3 in 75% yield. A five-step conversion of 3 to N1-Alloc-6-(N-Boc-aminomethyl)-1-azaspiro[4.4]nonane-2-acetic acid 1 provides access to a unique tri-functionalized scaffold for combinatorial chemistry.

  dra 4在乙醇中进行串联分子内迈克尔加成反应-分子内偶氮甲亚胺亚胺在乙醇中的环加成反应，以75％的收率得到三环吡唑啉甲基酯3。的五步转换3到N 1 -alloc基-6-（N-BOC-氨基甲基）-1-氮杂螺[4.4]壬烷-2-乙酸1访问用于组合化学独特的三官能化的支架。
• Structure–activity relationship of anti-malarial spongean peroxides having a 3-methoxy-1,2-dioxane structure
  作者：Motoyuki Kawanishi、Naoyuki Kotoku、Sawako Itagaki、Toshihiro Horii、Motomasa Kobayashi

  DOI：10.1016/j.bmc.2004.04.051

  日期：2004.10

  In order to study the structure-activity relationship of anti-malarial spongean peroxides, several analogues concerning with the 6-methoxyacetyl moiety and the 3-pentyl residue in methyl 2-(3-methoxy-3-pentyl-1,2-dioxan-6-yl) acetate were synthesized and evaluated for anti-malarial activity. The tert-butyl ester analogue 14 showed stability in mouse serum and a high selectivity index against the malaria parasite, Plasmodium falciparum, and the citronellyl analogue 31 exhibited the strongest in vitro antimalarial activity among them, and the imidazole analogue 25 showed desirable in vivo anti-malarial activity against P. berghei infected mice. (C) 2004 Elsevier Ltd. All rights reserved.
• ARMSTRONG, PAUL;GRIGG, RONALD;SURENDRAKUMAR, SIVAGNANASUNDRAM;WARNOCK, WI+, J. CHEM. SOC. CHEM. COMMUN.,(1987) N 17, 1327-1328
  作者：ARMSTRONG, PAUL、GRIGG, RONALD、SURENDRAKUMAR, SIVAGNANASUNDRAM、WARNOCK, WI+

  DOI：——

  日期：——
• Synthesis of a bioprobe for elucidation of target molecule of spongean anti-malarial peroxides
  作者：Nobutoshi Murakami、Motoyuki Kawanishi、Sawako Itagaki、Toshihiro Horii、Motomasa Kobayashi

  DOI：10.1016/j.bmcl.2004.04.086

  日期：2004.7

  The reactants of an anti-malarial peroxide having a 6-carbomethoxymethyl-3-methoxy-1,2-dioxane moiety treated with FeSO4 were analyzed. For mechanistic study of the anti-malarial peroxide, two biotinylated probes to elucidate the target molecules were designed and synthesized. The two synthesized probes showed potent anti-malarial activity, and one of them was proved to form an irreversible binding with protein in a model experiment. (C) 2004 Elsevier Ltd. All rights reserved.