(Z)-5-pentadecen-1-ol | 172995-30-1

• 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: (Z)-5-pentadecen-1-ol
• 英文别名: (Z)-pentadec-5-en-1-ol
• CAS: 172995-30-1
• 化学式: C₁₅H₃₀O
• 分子量: 226.403
• InChiKey: XEYHTKFVKXISSJ-KHPPLWFESA-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：

  (Z)-5-pentadecen-1-ol 在 sodium hydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (Z)-2-methoxy-1,1,1-tris(methylsulfanyl)hexadec-6-ene
  参考文献：
  名称：

  从加勒比海海绵中分离出的α-甲氧基化脂肪酸合成中的一种不寻常的硼辅助取代

  摘要：

  4-溴-1-丁基-9-BBN的Suzuki-Miyaura交叉偶联可产生4-羟基丁基产物，这显然是由硼辅助的氢氧化物取代引起的。该过程用于合成（±）-2-甲氧基-5Z-十六碳烯酸甲酯（1），其是从加勒比海海绵（Spheciospongia cuspidifera）分离的磷脂的衍生物。

  DOI：

  10.1016/s0040-4039(98)00515-2
• 作为产物：
  描述：

  1-十一炔 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 9-borabicyclo[3.3.1]nonane dimer 、 四(三苯基膦)钯 、 silver nitrate 、 C.I.酸性橙108 、 溶剂黄146 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 5.0h， 生成 (Z)-5-pentadecen-1-ol
  参考文献：
  名称：

  从加勒比海海绵中分离出的α-甲氧基化脂肪酸合成中的一种不寻常的硼辅助取代

  摘要：

  4-溴-1-丁基-9-BBN的Suzuki-Miyaura交叉偶联可产生4-羟基丁基产物，这显然是由硼辅助的氢氧化物取代引起的。该过程用于合成（±）-2-甲氧基-5Z-十六碳烯酸甲酯（1），其是从加勒比海海绵（Spheciospongia cuspidifera）分离的磷脂的衍生物。

  DOI：

  10.1016/s0040-4039(98)00515-2

文献信息

• Facile Total Synthesis and Antimicrobial Activity of the Marine Fatty Acids (<i>Z</i>)-2-Methoxy-5-hexadecenoic Acid and (<i>Z</i>)-2-Methoxy-6-hexadecenoic Acid
  作者：Néstor M. Carballeira、Anastacio Emiliano、Norali Hernández-Alonso、Fernando A. González

  DOI：10.1021/np980274o

  日期：1998.12.1

  The total synthesis of the naturally occurring (Z)-2-methoxy-5-hexadecenoic acid and (Z)-2-methoxy-6-hexadecenoic acid was accomplished using as a key step Mukaiyama's trimethylsilyl cyanide addition to 4- and 5-pentadecenal, respectively. These syntheses further confirm the structures of the natural marine fatty acids and corroborate their cis double-bond stereochemistry. The title compounds were

  天然存在的（Z）-2-甲氧基-5-十六碳烯酸和（Z）-2-甲氧基-6-十六碳烯酸的全合成是通过使用Mukaiyama的三甲基甲硅烷基氰化物加到4-和5-戊烯醛中作为关键步骤完成的， 分别。这些合成进一步证实了天然海洋脂肪酸的结构并证实了其顺式双键立体化学。标题化合物对革兰氏阳性菌金黄色葡萄球菌（MIC 0.35 micromol / mL）和粪链球菌（MIC 0.35 micromol / mL）具有抗菌作用。
• 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.
• KELKAR, S. V.;REDDY, G. BHASKAR;KULKARNI, G. H., INDIAN J. CHEM. B, 28,(1989) N1, C. 980-981
  作者：KELKAR, S. V.、REDDY, G. BHASKAR、KULKARNI, G. H.

  DOI：——

  日期：——
• An unusual boron-assisted substitution in the synthesis of α-methoxylated fatty acids isolated from Caribbean sponges
  作者：John A. Soderquist、Izander Rosado、Yernan Marrero

  DOI：10.1016/s0040-4039(98)00515-2

  日期：1998.5

  Suzuki-Miyaura cross coupling of 4-bromo-1-butyl-9-BBN produces 4-hydroxybutyl products evidently arising from a boron-assisted hydroxide substitution. This process was utilized in the synthesis of (±)-2-methoxy-5Z-hexadecenoic acid methyl ester (1), a derivative of the phospholipids isolated from the Caribbean sponge, Spheciospongia cuspidifera.

  4-溴-1-丁基-9-BBN的Suzuki-Miyaura交叉偶联可产生4-羟基丁基产物，这显然是由硼辅助的氢氧化物取代引起的。该过程用于合成（±）-2-甲氧基-5Z-十六碳烯酸甲酯（1），其是从加勒比海海绵（Spheciospongia cuspidifera）分离的磷脂的衍生物。