(10Z)-10-十五碳烯-1-醇 | 64437-42-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (10Z)-10-十五碳烯-1-醇
• 英文名称: (10Z)-10-pentadecen-1-ol
• 英文别名: (Z)-10-pentadecen-1-ol；(10Z)-pentadecen-1-ol；Z-10-pentadecen-1-ol；10Z-pentaadecenol；10-pentadecenol；pentadec-10c-en-1-ol；Z-10-Pentadecenol；(Z)-pentadec-10-en-1-ol
• CAS: 64437-42-9
• 化学式: C₁₅H₃₀O
• 分子量: 226.403
• InChiKey: YWAXGXIQALUWKR-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  16
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (10Z)-10-十五碳烯-1-醇 在 正丁基锂 、 sodium ethanolate 、 三溴化磷 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 27.0h， 生成 (3E,13Z)-十八碳二烯-1-基乙酸酯
  参考文献：
  名称：

  Vinczer, Peter; Juvancz, Zoltan; Novak, Lajos, Acta Chimica Hungarica, 1988, vol. 125, # 6, p. 797 - 820

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 10,11-dihydroxyundecanoate 在 lead(IV) acetate 、 lithium aluminium tetrahydride 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 35.0h， 生成 (10Z)-10-十五碳烯-1-醇
  参考文献：
  名称：

  A novel stereocontrolled synthesis of (z,z)-3,13-octadecadien-1-yl acetate, the sex pheromone of synanthedon species

  摘要：

  DOI：

  10.1016/s0040-4039(01)81267-3

文献信息

• Isolation, structure and synthesis of maesanin, a host defense stimulant from an African medicinal platn maesa lanceolata
  作者：Isao Kubo、Tadao Kamikawa、Iwao Miura

  DOI：10.1016/s0040-4039(00)94285-0

  日期：1983.1

  The isolation, characterization and an efficient synthesis of maesanin , a host defense stimulant isolated from an African medicinal plant Maesa lanceolata is reported.

  据报道，从非洲药用植物毛叶曼萨（Maesa lanceolata）中分离出的一种宿主防御刺激剂—迈萨宁（Maesanin）的分离，表征和有效合成。
• Isolation, structure and synthesis of maesanin, a host defense stimulant from an african medicinal plant
  作者：Isao Kubo、Mujo Kim、Iraj Ganjian、Tadao Kamikawa、Yoshiro Yamagiwa

  DOI：10.1016/s0040-4020(01)86870-8

  日期：1987.1

  The isolation, characterization and an efficient synthesis of maesanin 1, a host defense stimulant isolated from an African medicinal plant Maesalanceolata, is reported.

  据报道，从非洲药用植物Maesalanceolata分离出的宿主防御刺激物maesanin 1的分离，表征和有效合成。
• Synthesis of insect sex pheromones and their homologues. 2. A convenient method for synthesizing (Z)-alkenols and their acetates.
  作者：Michio HORIIKE、Masaru TANOUCHI、Chisato HIRANO

  DOI：10.1271/bbb1961.44.257

  日期：——

  (Z)-Alkenols and Their acetates have been synthesized by the Wittig reaction of (ω-hydroxyalkyl)triphenylphosphonium salts with alkanals by a convenient procedure. The geometrical purity of the products was evaluated to be no less than 95% of the (Z)-configu-ration by means of GLC with a glass capillary column coated with CHDMS.

  通过一种简便的方法，利用Wittig反应将（ω-羟基烷基）三苯基膦盐与烷基醛反应，合成了（Z）-烯醇及其乙酸酯。通过涂有CHDMS的玻璃毛细管柱进行GC分析，评估产物的几何纯度不小于95%的（Z）构型。
• A novel stereocontrolled synthesis of (z,z)-3,13-octadecadien-1-yl acetate, the sex pheromone of synanthedon species
  作者：Péter Vinczer、Gábor Baán、Lajos Novák、Csaba Szántay

  DOI：10.1016/s0040-4039(01)81267-3

  日期：1984.1
• Structure Determination of an Endogenous Sleep-Inducing Lipid, <i>cis</i>-9-Octadecenamide (Oleamide):  A Synthetic Approach to the Chemical Analysis of Trace Quantities of a Natural Product
  作者：Benjamin F. Cravatt、Richard A. Lerner、Dale L. Boger

  DOI：10.1021/ja9532345

  日期：1996.1.1

  The pursuit of endogenous sleep-inducing substances has been the focus of an extensive, complicated body of research. Several compounds, including Delta-sleep-inducing peptide and prostaglandin D-2, have been suggested to play a role in sleep induction, and yet, the molecular mechanisms of this physiological process remain largely unknown. In recent efforts, the cerebrospinal fluid of deep-deprived cats was analyzed in search of compounds that accumulated during sleep deprivation. An agent with the chemical formula C18H35NO was found to cycle with sleep-wake patterns, increasing in concentration with sleep deprivation and decreasing in amount upon recovery sleep. Since the material was generated in minute quantities and only under the special conditions of sleep deprivation, efforts to isolate sufficient material for adequate characterization, structure identification, and subsequent detailed evaluation of its properties proved unrealistic. With the trace amounts of the impure endogenous compound available, extensive MS studies on the agent were completed, revealing key structural features of the molecule including two degrees of unsaturation, a long alkyl chain, and a nitrogen substituent capable of fragmenting as ammonia. Additionally, HPLC traces suggested a weak UV absorbance for the unknown material. With this data in hand and encouraged by the relatively small size of the molecule, MW = 281, a synthetic approach toward the structural identification of the natural compound was initiated. Herein, we report the full details of the synthesis and comparative characterization of candidate structures for this endogenous agent that led to the unambiguous structural correlation with synthetic cis-9-octadecenamide.