(Z)-2-十五碳烯-1-醇 | 2907-52-0

• 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: (Z)-2-十五碳烯-1-醇
• 英文名称: (Z)-2-pentadecen-1-ol
• 英文别名: (Z)-pentadec-2-en-1-ol；(Z)-2-pentadecenol；cis-Δ²-Pentadecen-1-ol；pentadec-2c-en-1-ol
• CAS: 2907-52-0
• 化学式: C₁₅H₃₀O
• 分子量: 226.403
• InChiKey: GZIKTBWNIYAWLH-YPKPFQOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 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)-2-十五碳烯-1-醇 在 chromium(VI) oxide 、 叔丁醇 作用下， 生成 pentadec-2-enoic acid
  参考文献：
  名称：

  Grimmer,G.; Hildebrandt,A., Justus Liebigs Annalen der Chemie, 1965, vol. 685, p. 154 - 160

  摘要：

  DOI：
• 作为产物：
  描述：

  2-十五碳炔-1-醇 在 sodium tetrahydroborate 、 氢气 、 nickel(II) acetate tetrahydrate 、 乙二胺 作用下， 以 甲醇 为溶剂， 生成 (Z)-2-十五碳烯-1-醇
  参考文献：
  名称：

  通过同源混合物的组合合成构建挥发性化合物的化学文库：Alk-4-en-1-ols、Alk-4-enals 和 Methyl Alk-4-enoates

  摘要：

  包含 66 个线性化合物的化合物库，六个分子家族的 11 个代表：( E )- 和 ( Z )-alk-4-en-1-ols、alk-4-enals 和甲基 alk-4-enoates 的异构体, 是通过组合合成制备的, 以允许创建直接可用于在 GC/MS 分析中识别它们的质谱数据库。我们在这里证明化合物库可以通过使用长线性合成序列的组合合成来制备，即。即，在 4-enals 的情况下为八步。由此产生的同系物混合物仍然可以完美地用于提供所需的信息，例如干净的质谱和良好的气相色谱保留指数。

  DOI：

  10.1002/cbdv.202200817

文献信息

• Extended structural modulation of bio-inspired chiral lipidic alkynylcarbinols as antitumor pharmacophores
  作者：Dymytrii Listunov、Chelmia Billot、Etienne Joly、Isabelle Fabing、Yulian Volovenko、Yves Génisson、Valérie Maraval、Remi Chauvin

  DOI：10.1016/j.tet.2015.08.003

  日期：2015.10

  (SAR) study from the (S,E)-eicos-4-en-1-yl-3-ol natural reference 1, the (S)-dialkynylcarbinol unit of the non-natural dehydro derivative 2 emerged as an unprecedented anti-tumoral pharmacophore. An extended study of lipidic alkynylcarbinol pharmacophores is presented, addressing additional structural parameters: Z→E isomerization of the alkenyl carbinol substituent of 1, variation of the lipidic chain

  通常在天然海产品中发现的手性炔基甲醇基因其药效学特性，特别是对肿瘤细胞系的细胞毒性而成为研究热点。在从化学合成驱动四参数结构-活性关系（SAR）研究（小号，ê）-eicos -4-烯-1-基-3-醇自然参考1中，（小号的）-dialkynylcarbinol单元非天然脱氢衍生物2成为一个前所未有的抗肿瘤药效。脂质alkynylcarbinol药效的扩展研究提出，寻址附加结构参数：ž→Ë的链烯基甲醇取代基的异构化1，的脂质链长度的变异2（C 3N，Ñ = 3,4，6），氧化或的甲醇单元的取代2（以酮，叔苯基甲基甲醇，或甲基醚）中，双键的cyclomethylenation 1。这些类似物的合成所描述的，包括使用用于锌-介导的另外的（三烷基甲硅烷基）乙炔基片到ynals在存在改性Carreira的过程对映体富集的手性alkynylcarbinol衍生物的制备（ - ） -或（+） - ñ -甲基麻黄碱。的12个新产品针对HCT
• Synthesis of (–)-Muricatacin
  作者：Hidefumi Makabe、Akira Tanaka、Takayuki Oritani

  DOI：10.1271/bbb.57.1028

  日期：1993.1

  The synthesis of (–)-muricatacin starting from 1-bromododecane and 2-pentyn-l-ol is described. 2-Pentadecyn-1-ol (4), which was prepared from 1-bromododecane (2) and 2-pentyn-1-ol (3), was converted to epoxy alcohol 6 through a two-step reaction sequence, 6 being successively submitted to tosylation, iodination, chain extension with tert-butyl lithioacetate, and acid-catalyzed cyclization to give (–)-muricatacin (1a). Recrystallization afforded optically pure 1a.

  本文介绍了从 1-溴十二烷和 2-戊炔-1-醇开始合成 (-)-muricatacin 的方法。2-Pentadecyn-1-ol (4) 由 1-bromododecane (2) 和 2-Pentyn-1-ol (3) 制备而成，通过两步反应顺序将其转化为环氧醇 6，6 依次经过甲磺酰化、碘化、用硫代乙酸叔丁酯进行链延伸和酸催化环化，得到 (-)-muricatacin (1a)。重结晶后得到光学纯度为 1a。
• 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.
• JPH06256336A
  申请人：——

  公开号：JPH06256336A

  公开（公告）日：1994-09-13