6-hydroxy-oct-7-enoic acid methyl ester | 3111-94-2

• 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: 6-hydroxy-oct-7-enoic acid methyl ester
• 英文别名: methyl 6-hydroxy-7-octenoate；Methyl-6-hydroxy-7-octenoat；Methyl 6-hydroxyoct-7-enoate
• CAS: 3111-94-2；114825-70-6
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: VIEFQHRCIDOIEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-hydroxy-oct-7-enoic acid methyl ester 在 双氧水 、 sodium acetate 、 diborane(6) 作用下， 生成 6,8-dihydroxyoctanoic acid methyl ester
  参考文献：
  名称：

  Rao, A. V. Rama; Mysorekar, Sudha V.; Yadav, J. S., Synthetic Communications, 1987, vol. 17, # 11, p. 1339 - 1348

  摘要：

  DOI：
• 作为产物：
  描述：

  壬二酸 在 lead(IV) acetate 、 叔丁基过氧化氢 、 barium dihydroxide 、 selenium(IV) oxide 、 copper diacetate 、 二甲基硫 、 硫酸 作用下， 以 吡啶 、 甲醇 、 苯 为溶剂， 反应 46.0h， 生成 6-hydroxy-oct-7-enoic acid methyl ester
  参考文献：
  名称：

  Rao, A. V. Rama; Mysorekar, Sudha V.; Yadav, J. S., Synthetic Communications, 1987, vol. 17, # 11, p. 1339 - 1348

  摘要：

  DOI：

文献信息

• Catalytic Aza-Wacker Annulation: Tuning Mechanism by the Activation Mode of Amide and Enantioselective Syntheses of Melinonine-E and Strychnoxanthine
  作者：Changmin Xie、Jisheng Luo、Yuping Zhang、Sha-Hua Huang、Lili Zhu、Ran Hong

  DOI：10.1021/acs.orglett.8b00725

  日期：2018.4.20

  to establish 2-azabicyclo[3.3.1]nonane and other ring skeletons in good yield. The novel catalytic aza-Wacker annulation methodology was further illustrated in the concise syntheses and the absolute configuration determinations of melinonine-E and strychnoxanthine.

  人们发现，空前的酰胺N取代基对于成功成环以高产率建立2-氮杂双环[3.3.1]壬烷和其他环骨架至关重要。简洁的合成方法以及对melinonine-E和strychnoxanthine的绝对构型测定进一步说明了新颖的催化aza-Wacker环化方法。
• Stereoselective Synthesis of a Protected Form of (6<i>R</i>,7<i>E</i>,9<i>S</i>,10<i>R</i>,12<i>Z</i>)-6,9,10-Trihydroxy-7,12-hexadecadienoic Acid
  作者：Yusuke KURASHINA、Shigefumi KUWAHARA

  DOI：10.1271/bbb.110829

  日期：2012.3.23

  The protected stereoisomer of a trihydroxy unsaturated fatty acid, which could be employed as a potential nigricanoside α-chain building block, was synthesized by using Evans asymmetric alkylation, Sharpless kinetic resolution, and diastereoselective reduction as the key steps.

  通过埃文斯不对称烷基化、夏普勒斯动力学解析和非对映选择性还原等关键步骤，合成了一种三羟基不饱和脂肪酸的受保护立体异构体，该立体异构体可用作潜在的黑果苷 α-链构建基块。
• Three-step synthesis of oxylipins from D. loretense
  作者：Shreyosree Chatterjee、Gayan A. Abeykoon、Jason S. Chen

  DOI：10.1016/j.tetlet.2019.06.040

  日期：2019.7

  A three-step convergent synthesis of an immunostimulatory oxylipin was developed using an olefin cross metathesis approach. The alkene fragments were prepared in two steps from commercially available starting materials with high stereoselectivity. In particular, an organocatalytic aldehyde α-oxygenation gave high enantioselectivity and yield using as little as 2 mol% catalyst. This synthesis represents

  使用烯烃交叉复分解方法开发了免疫刺激性磷脂的三步收敛合成法。用高立体选择性从市售起始原料分两步制备烯烃片段。特别地，使用少至2mol％的催化剂，有机催化的醛α-氧化给出了高的对映选择性和收率。该合成代表了任何含有3-ene-1,2,5-三醇部分的天然产物的最短合成，并以33％的总收率递送了免疫刺激性的脂蛋白。
• Three New Unsaturated Fatty Acids from the Marine Green Alga Ulva fasciata Delile
  作者：Ghada S. E. Abou-ElWafa、Mohamed Shaaban、Khaled A. Shaaban、Mohamed E. E. El-Naggar、Hartmut Laatsch

  DOI：10.1515/znb-2009-1014

  日期：2009.10.1

  From the dichloromethane extract of the marine green alga Ulva fasciata Delile, collected from the Mediterranean coast of Egypt, three new fatty acids, namely, (E)-11-oxo-octadeca-12-enoic acid (1a), (E)-11-hydroxy-octadeca-12-enoic acid (2a) and 6-hydroxy-oct-7-enoic acid (3a) together with cholesterol were isolated. Analysis of the unpolar part of the extract using GC-MS detected the existence of further ten compounds, namely, dimethylsulfoxide, dimethylsulfone, phenylacetamide, 6,10,14-trimethyl-pentadecan-2-one, 8-heptadecene, dodecane, tridecane, 4-oxo-pentanoic acid, hexadecanoic acid, and the naturally new 1,1ʹ-bicyclohexyl. Structures of the isolated compounds 1a - 3a were confirmed by spectroscopic analyses including mass spectra (EI-MS, HR/ESIMS), 1D and 2D NMR experiments, and by the synthetic conversion into their corresponding methyl esters 1b - 3b. The algal extract and its components were comparatively examined against several pathogenic microorganisms, and brine shrimps for cytotoxicity.

  从埃及地中海海岸采集的海洋绿藻Ulva fasciata Delile的二氯甲烷提取物中，分离出三种新的脂肪酸，分别是(E)-11-氧代十八碳十二烯酸（1a）、(E)-11-羟基十八碳十二烯酸（2a）和6-羟基辛-7-烯酸（3a），以及胆固醇。使用GC-MS分析提取物的非极性部分检测到另外十种化合物的存在，分别是二甲基亚砜、二甲基砜、苯乙酰胺、6,10,14-三甲基十五烷-2-酮、8-庚十七烯、十二烷、十三烷、4-氧代戊酸、十六烷酸和天然新的1,1'-双环己基。通过光谱分析，包括质谱（EI-MS，HR/ESIMS）、1D和2D NMR实验，以及合成转化为相应的甲酯1b-3b，确认了分离化合物1a-3a的结构。对海藻提取物及其组分进行了抗多种病原微生物和对溴盐虾的细胞毒性的比较研究。
• METHOD FOR PRODUCING OXYGEN-CONTAINING COMPOUND
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1609777A1

  公开（公告）日：2005-12-28

  It is provided that a method for producing an oxygen-containing compound, characterized in that an olefin compound having a carbon-carbon double bond which is bonded to a methyl or methylene group is reacted with an organic hydroperoxide in the presence of an ionic liquid and a selenium compound.

  本发明提供了一种生产含氧化合物的方法，其特征在于：在离子液体和硒化合物的存在下，使具有碳碳双键并与甲基或亚甲基键合的烯烃化合物与有机过氧化氢反应。