(3Z,6Z)-nona-3,6-dienyl p-toluenesulfonate | 161794-74-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3Z,6Z)-nona-3,6-dienyl p-toluenesulfonate
• 英文别名: [(3Z,6Z)-nona-3,6-dienyl] 4-methylbenzenesulfonate
• CAS: 161794-74-7
• 化学式: C₁₆H₂₂O₃S
• 分子量: 294.415
• InChiKey: MZYCRMXDQHZTBX-UTOQUPLUSA-N

物化性质

• 沸点：
  421.9±34.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3Z,6Z)-nona-3,6-dienyl p-toluenesulfonate 在 sodium hexamethyldisilazane 作用下， 以 乙腈 为溶剂， 反应 17.0h， 生成 (4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-二十二碳六烯酸乙酯
  参考文献：
  名称：

  New Synthon for the Convergent Construction of Skipped Conjugation Polyenes: Synthesis of Ethyl Docosa-4,7,10,13,16,19-hexaenoate

  摘要：

  The preparation and subsequent Wittig reaction of the (Z,Z)-phosphonium salt 4, a useful synthon for the preparation of skipped conjugation polyenes, are reported. Salt 4 is a key intermediate for the synthesis of ethyl docosa-4,7,10,13,16,19-hexaenoate (3b).

  DOI：

  10.1021/jo00106a026
• 作为产物：
  描述：

  2-戊炔-1-醇 在 Lindlar's catalyst 吡啶 、 喹啉 、 copper(l) iodide 、 四丁基氯化铵 、 氢气 、 sodium carbonate 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.5h， 生成 (3Z,6Z)-nona-3,6-dienyl p-toluenesulfonate
  参考文献：
  名称：

  Antioxidant Behaviour of Thia Fatty Acids

  摘要：

  作为花生四烯酸自氧化的抑制剂，对八种脂肪酸和其他硫化物进行了研究。这些抑制剂在不同程度上延长了氧化的滞后期。硫附近的羧基降低了抗氧化活性，而不饱和硫化物比饱和硫化物更有效。这些结果与硫化物减少脂肪酸氢过氧化物的作用是一致的，否则氢过氧化物会在反应的早期阶段积聚并扩展自由基氧化过程。

  DOI：

  10.1071/ch02095

文献信息

• Pheromone synthesis. Part 257: Synthesis of methyl (2E,4Z,7Z)-2,4,7-decatrienoate and methyl (E)-2,4,5-tetradecatrienoate, the pheromone components of the male dried bean beetle, Acanthoscelides obtectus (Say)
  作者：Kenji Mori

  DOI：10.1016/j.tet.2015.06.051

  日期：2015.8

  oxidation/Wittig reaction of (2Z,5Z)-2,5-octadien-1-ol yielded methyl (2E,4Z,7Z)-2,4,7-decatrienoate, a newly discovered pheromone component of the male dried bean beetle, while that of (±)-2,3-dodecadien-1-ol gave (±)-methyl (E)-2,4,5-tetradecatrienoate, the racemate of the known and major pheromone component. Methyl (2E,4E,7Z)-2,4,7-decatrienoate was also synthesized, which is the methyl ester of an acid metabolite

  （2 Z，5 Z）-2,5-辛二烯-1-醇的串联Dess-Martin氧化/维蒂希反应产生了新发现的（2 E，4 Z，7 Z）-2,4,7-癸三烯酸甲酯雄性干豆甲虫的信息素成分，而（±）-2,3-dodecadien-1-ol的信息素成分产生（±）-甲基（E）-2,4,5-十四碳三烯酸酯，是已知和主要的外消旋体信息素成分。还合成了（2 E，4 E，7 Z）-2,4,7-十碳三烯酸甲酯，它是绿藻酸代谢产物的甲酯。用Zn-Cu / EtOH还原2,5-辛二炔-1-醇可干净地得到（2 Z，5 Z）-2,5-辛二烯-1-醇。
• Anti-cancer nitro- and thia-fatty acids
  申请人：——

  公开号：US20030078299A1

  公开（公告）日：2003-04-24

  The present invention relates to pharmaceutical compositions comprising, as an anti-cancer agent: (a) one or more compounds having the formula NO 2 —A—B, 1 wherein A is a saturated or unsaturated hydrocarbon chain of 14-26 double bonds, and B is (CH 2 ) m (COOH) n in which n is a integer from 0 to 2 and m is an integer from 0 to 2; or a derivative thereof in which the hydrocarbon chain has one or more than one substitution selected from the group consisting of hydroxy, hydroperoxy, epoxy and peroxy; (b) one or more compounds selected from polyunsaturated fatty acids (PUFA's) having a 16 to 26 carbon atom chain and 3 to 16 double bonds, and wherein the PUFA is covalently coupled at the carboxylic acid group to an amino acid selected from glycine and aspartic acid; (c) one or more compounds selected from unsaturated fatty acids having an 18 to 25 carbon atom chain and 1 to 6 double bonds and wherein the fatty acid has one or two &bgr;-oxa, &ggr;-oxa, &bgr;-thia, &ggr;-thia substitutions: or (d) one or more compounds having formula (I) wherein A′ is a saturated or unsaturated hydrocarbon chain of 9-26 carbon atoms, X is oxygen or is absent and B′ is (CH 2 ) J (COOH) k in which j is an integer from 1 to 3 and K is 0 or 1; or a derivative thereof in which the hydrocarbon chain has one or more than one substitution selected from the group consisting of hydroxy, hydroperoxy, epoxy and peroxy; and a pharmaceutically acceptable carrier or diluent.

  本发明涉及制药组合物，包括作为抗癌剂的：(a) 一个或多个具有式NO2—A—B,1的化合物，其中A是14-26个双键的饱和或不饱和碳氢链，B是(CH2)m(COOH)n，其中n是0到2的整数，m是0到2的整数；或其衍生物，其中碳氢链具有羟基、过氧化氢基、环氧基和过氧基中的一种或多种取代；(b) 一种或多种选择自具有16到26个碳原子链和3到16个双键的多不饱和脂肪酸（PUFA），其中PUFA在羧酸基上与选择自甘氨酸和天冬氨酸的氨基酸共价耦合；(c) 一种或多种选择自具有18到25个碳原子链和1到6个双键的不饱和脂肪酸，其中脂肪酸具有一或两个β-氧杂、γ-氧杂、β-硫杂、γ-硫杂取代；或(d) 公式(I)中A′是9-26个碳原子的饱和或不饱和碳氢链，X是氧或不存在，B′是(CH2)J(COOH)k，其中j是1到3的整数，k是0或1；或其衍生物，其中碳氢链具有羟基、过氧化氢基、环氧基和过氧基中的一种或多种取代；以及药学上可接受的载体或稀释剂。
• First total synthesis of pro-resolving and tissue-regenerative resolvin sulfido-conjugates
  作者：Ana R. Rodriguez、Bernd W. Spur

  DOI：10.1016/j.tetlet.2017.03.041

  日期：2017.4

  The first total synthesis of the pro-resolving and tissue-regenerative resolvin sulfido-conjugates: 7S,8R,17S-RCTR1, 7S,8R,17S-RCTR2 and 7S,8R,17S-RCTR3, derived from docosahexaenoic acid, has been achieved. Two synthetic approaches are described. Chiral centers 7S and 8R were introduced in both approaches via a chiral pool strategy starting from 2-deoxy-d-ribose. The 17S chiral center was introduced

  促分辨和组织再生性RESOLVIN硫键结合物的第一个全合成：7 S，8 R，17 S -RCTR1，7 S，8 R，17 S -RCTR2和7 S，8 R，17 S -RCTR3已经获得了源自二十二碳六烯酸的化合物。描述了两种合成方法。手性中心7小号和8 - [R在两个引入通过从2-脱氧起始手性池策略接近d -核糖。17 S通过手性池策略或通过脂氧化酶的酶促羟基化引入手性中心。Wittig反应，分别与谷胱甘肽，1-半胱氨酰甘氨酸和1-半胱氨酸的选择性环氧化物形成和环氧化物打开是合成的关键步骤。
• HETEROATOM CONTAINING SUBSTITUTED FATTY ACIDS
  申请人：Miller Raymond A.

  公开号：US20110082206A1

  公开（公告）日：2011-04-07

  Activated fatty acids, pharmaceutical compositions including activated fatty acids, methods for using activated fatty acids to treat a variety of diseases, and methods for preparing activated fatty acids are provided herein.

  本文提供了活化脂肪酸、包括活化脂肪酸的制药组合物、使用活化脂肪酸治疗各种疾病的方法以及制备活化脂肪酸的方法。
• Anti-inflammatory nitro and thia-fatty acids
  申请人：——

  公开号：US20030092762A1

  公开（公告）日：2003-05-15

  The present invention relates to compounds of the general formula: NO 2 -A-B wherein A is a saturated or unsaturated hydrocarbon chain of 14-26 carbon atoms and B is (CH 2 ) n (COOH) m in which n is an integer from 0 to 2 and m is an integer from 0 to 2; or of general formula (I), wherein A′ is a saturated or unsaturated hydrocarbon chain of 9-26 carbon atoms, X is oxygen or is absent and B′ is (CH 2 ) j (COOH) k in which j is an integer from 1 to 3 and k is 0 or 1; and the derivatives thereof in which the hydrocarbon chain includes one or more than one substitution selected from the group consisting of hydroxy, hydroperoxy, epoxy and peroxy. These compounds have biological activity, e.g. as anti-infective or anti-inflammatory agents.

  本发明涉及一般式为：NO2-A-B的化合物，其中A是14-26个碳原子的饱和或不饱和碳氢链，B是(CH2)n(COOH)min，其中n是0到2的整数，m是0到2的整数；或一般式(I)的化合物，其中A′是9-26个碳原子的饱和或不饱和碳氢链，X是氧或不存在，B′是(CH2)j(COOH)kin，其中j是1到3的整数，k是0或1；以及其衍生物，其中碳氢链包括一个或多个羟基，过氧化氢基，环氧基和过氧基的取代。这些化合物具有生物活性，例如作为抗感染或抗炎剂。