(7-methoxycarbonylheptyl)triphenylphosphonium bromide

• 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: (7-methoxycarbonylheptyl)triphenylphosphonium bromide
• 英文别名: (7-carbomethoxyheptyl)triphenylphosphonium bromide；Methyl-8-triphenylphosphoranyl-octanoate bromide；(8-methoxy-8-oxooctyl)-triphenylphosphanium;bromide
• 化学式: Br*C₂₇H₃₂O₂P
• 分子量: 499.428
• InChiKey: HQANCSWLWKKBCF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (7-methoxycarbonylheptyl)triphenylphosphonium bromide 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 sodium methylate 作用下， 以 水 为溶剂， 反应 22.5h， 生成 10,13-环氧-11-甲基十八碳-10,12-二烯酸
  参考文献：
  名称：

  Tsukasa, Hidetaka, Bioscience, Biotechnology and Biochemistry, 1993, vol. 57, # 3, p. 511 - 512

  摘要：

  DOI：
• 作为产物：
  描述：

  8-溴辛酸 在 盐酸 作用下， 以 乙腈 为溶剂， 反应 60.0h， 生成 (7-methoxycarbonylheptyl)triphenylphosphonium bromide
  参考文献：
  名称：

  鉴定和从加勒比海绵花萼足的新合成二甲基化脂肪酸。

  摘要：

  自然界中首次在加勒比海海绵花萼中发现了二甲基化脂肪酸9,13-二甲基十四烷酸，它与稀有的10,13-二甲基十四烷酸一起出现。使用GC-MS，吡咯烷化物衍生化以及从8-溴辛酸开始的五步全合成完成了新化合物的表征。还描述了稀有的10，13-二甲基十四烷酸的首次外消旋全合成。

  DOI：

  10.1021/np990529d

文献信息

• Identification and Total Synthesis of a Novel Dimethylated Fatty Acid from the Caribbean Sponge <i>Calyx podatypa</i>
  作者：Néstor M. Carballeira、Mayra Pagán

  DOI：10.1021/np990529d

  日期：2000.5.1

  dimethylated fatty acid 9,13-dimethyltetradecanoic acid was identified for the first time in nature in the Caribbean sponge Calyx podatypa where it occurs together with the rare 10, 13-dimethyltetradecanoic acid. The characterization of the novel compound was accomplished using GC-MS, pyrrolidide derivatization, and a five-step total synthesis starting with 8-bromooctanoic acid. The first racemic total synthesis

  自然界中首次在加勒比海海绵花萼中发现了二甲基化脂肪酸9,13-二甲基十四烷酸，它与稀有的10,13-二甲基十四烷酸一起出现。使用GC-MS，吡咯烷化物衍生化以及从8-溴辛酸开始的五步全合成完成了新化合物的表征。还描述了稀有的10，13-二甲基十四烷酸的首次外消旋全合成。
• Design, synthesis, and biological evaluation of 1, 3-disubstituted-pyrazole derivatives as new class I and IIb histone deacetylase inhibitors
  作者：Yiwu Yao、Chenzhong Liao、Zheng Li、Zhen Wang、Qiao Sun、Chunping Liu、Yang Yang、Zhengchao Tu、Sheng Jiang

  DOI：10.1016/j.ejmech.2014.09.024

  日期：2014.10

  A novel series of HDAC inhibitors demonstrating class I and IIb subtype selectivity have been identified using a scaffold-hopping strategy. Several designed compounds showed better selectivity for class I and IIb over class IIa HDAC isoforms comparing to the FDA approved HDAC targeting drug SAHA. A representative lead compound 22 bearing a biphenyl moiety demonstrated promising class I and IIb HDAC

  使用脚手架跳槽策略已鉴定出一系列新的HDAC抑制剂，可证明I类和IIb类亚型选择性。与FDA批准的HDAC靶向药物SAHA相比，几种设计的化合物对I和IIb的选择性优于IIa类的HDAC同工型。带有联苯部分的代表性铅化合物22表现出有希望的I和IIb类HDAC同工型选择性和对几种癌细胞的体外抗癌活性。这项工作可以作为使用设计的分子支架进一步探索选择性HDAC抑制剂的基础平台。
• 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.
• Tsukasa, Hidetaka, Bioscience, Biotechnology and Biochemistry, 1993, vol. 57, # 3, p. 511 - 512
  作者：Tsukasa, Hidetaka

  DOI：——

  日期：——
• The Isolation and Synthesis of Novel Nematocidal Dithiocyanates from an Australian Marine Sponge, <i>Oceanapia </i>sp.
  作者：Robert J. Capon、Colin Skene、Edward Hsiang-Te Liu、Ernest Lacey、Jennifer H. Gill、Kirstin Heiland、Thomas Friedel

  DOI：10.1021/jo0106750

  日期：2001.11.1

  Bioassay-directed fractionation of the EtOH extract of an Oceanapia sp. collected off the northern Rottnest Shelf, Australia, has yielded three novel dithiocyanates, thiocyanatins A (1), B (2a), and C (2b). The structures were determined by detailed spectroscopic analysis and confirmed by total synthesis. In addition to featuring an unprecedented dithiocyanate functionality, thiocyanatins possess an unusual 1,16-difunctionalized n-hexadecane carbon skeleton and are revealed as a hitherto unknown class of nematocidal agents