<6-(Tetrahydro-2-pyranyloxy)hexyl>-triphenylphosphonium-bromid | 79837-75-5

• 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: <6-(Tetrahydro-2-pyranyloxy)hexyl>-triphenylphosphonium-bromid
• 英文别名: (6-tetrahydropyranyloxyhexyl)triphenylphosphonium bromide；6-(Oxan-2-yloxy)hexyl-triphenylphosphanium;bromide
• CAS: 79837-75-5
• 化学式: Br*C₂₉H₃₆O₂P
• 分子量: 527.481
• InChiKey: YSHIHRBUKMMQHO-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <6-(Tetrahydro-2-pyranyloxy)hexyl>-triphenylphosphonium-bromid 在 水 、 sodium hexamethyldisilazane 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 (6Z,10Z)-6,10-Tetradecadien-1-ol
  参考文献：
  名称：

  信息素XLI。1,5-和1,6-链二烯的立体选择性合成作为性信息素和信息素类似物

  摘要：

  以“模块化系统”的方式，乙酸二烯基酯，链二烯醇和链二烯醛（它们被称为雌性蝴蝶的性信息素）是通过双键被乙烯或三亚甲基（1,5或1,6链二烯）打断而合成的。位置和几何形状。

  DOI：

  10.1002/jlac.198219820807
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 <6-(Tetrahydro-2-pyranyloxy)hexyl>-triphenylphosphonium-bromid
  参考文献：
  名称：

  Synthesis and Preliminary PET Imaging Studies of a FAAH Radiotracer ([¹¹C]MPPO) Based on α-Ketoheterocyclic Scaffold

  摘要：

  Fatty acid amide hydrolase (FAAH) is one of the principle enzymes for metabolizing endogenous cannabinoid neurotransmitters such as anandamide, and thus regulates endocannabinoid (eCB) signaling. Selective pharmacological blockade of FAAH has emerged as a potential therapy to discern the endogenous functions of anandamide-mediated eCB pathways in anxiety, pain, and addiction. Quantification of FAAH in the living brain by positron emission tomography (PET) would help our understanding of the endocannabinoid system in these conditions. While most FAAH radiotracers operate by an irreversible ("suicide") binding mechanism, a FAAH tracer with reversibility would facilitate quantitative analysis. We have identified and radiolabeled a reversible FAAH inhibitor, 7-(2-[C-11]methoxyphenyl)-1- (5-(pyridin-2-yl)oxazol-2-yl)heptan-1-one ([C-11]MPPO) in 13% radiochemical yield (nondecay corrected) with >99% radiochemical purity and 2 Ci/mu mol (74 GBq/mu mol) specific activity. The tracer showed moderate brain uptake (0.8 SUV) with heterogeneous brain distribution. However, blocking studies with a potent FAAH inhibitor URB597 demonstrated a low to modest specificity to the target. Measurement of lipophilicity, metabolite, and efflux pathway analysis were also performed to study the pharmacokinetic profile of [C-11]MPPO. In all, we reported an efficient radiolabeling and preliminary evaluation of the first-in-class FAAH inhibitor [C-11]MPPO with alpha-ketoheterocyclic scaffold.

  DOI：

  10.1021/acschemneuro.5b00248

文献信息

• An easy access to symmetrical Z-olefins from phosphorus ylides
  作者：S. Poulain、N. Noiret、H. Patin

  DOI：10.1016/0040-4039(96)01737-6

  日期：1996.10

  Symmetrical Z-olefins are obtained in good to quantitative yields from phosphonium salts via an autoxidation process, in salt-free conditions.

  在无盐条件下，通过自氧化过程，可以从phospho盐以良好的定量收率获得对称的Z-烯烃。
• Synthetic Approaches to Novel Archaeal Tetraether Glycolipid Analogues
  作者：Grégory Lecollinet、Rachel Auzély-Velty、Mathieu Danel、Thierry Benvegnu、Grahame Mackenzie、John W. Goodby、Daniel Plusquellec

  DOI：10.1021/jo9822028

  日期：1999.4.1

  Symmetrical and unsymmetrical archaeal tetraether glycolipid analogues have been prepared. The syntheses are based upon the elaboration of lipid cores from versatile chiral starting materials followed by simultaneous or sequential introduction of polar headgroups. Three pathways (A-C) were elaborated for the synthesis of stereochemically defined lipids 14-16 characterized by a straight bridging spacer

  已经制备了对称和不对称的古细菌四醚糖脂类似物。合成是基于从多种手性起始原料精制脂质核心，然后同时或相继引入极性头基。阐述了合成立体化学定义的脂质14-16的三个途径（AC），这些脂质的特征是直连接间隔基和两个分别在sn-3和sn-2位置与甘油单元相连的二氢香茅烷基链。途径C似乎对于合成四醚9特别有利，该四醚9具有在嗜热嗜酸脂质中发现的环戊烷单元。通过二醇14-16与β-D-半乳糖呋喃糖基供体31的反应，以49-53％的产率生产了二糖基化脂质4-6。
• Pheromone, XXXII. Bausteine zur Darstellung zweifach ungesättigter Schmetterlings-pheromone
  作者：Hans Jürgen Bestmann、Karl Heinrich Koschatzky、Wilfried Schätzke、Joachim Süß、Otto Vostrowsky

  DOI：10.1002/jlac.198119810920

  日期：1981.9.21

  Die Darstellung α,ω-bifunktioneller Ausgangsverbindungen sowie (Z)- und (E)-konfigurierter, ungesättigter Synthesebausteine, die man mittels Wittig-Reaktion, Michael-Addition, Acetylen-synthese oder Crombie-Reaktion erhält, wird beschrieben. Diese Verbindungen werden im Rahmen eines „Baukastensystems” zur Synthese bisolefinischer Sexualpheromone benötigt.

  描述了通过Wittig反应，Michael加成，乙炔合成或Crombie反应获得的α，ω-双功能起始化合物以及（Z）和（E）构型的不饱和合成结构单元的表示。这些化合物是合成双烯烃性信息素的“模块系统”的一部分。
• Synthesis and Preliminary PET Imaging Studies of a FAAH Radiotracer ([¹¹C]MPPO) Based on α-Ketoheterocyclic Scaffold
  作者：Lu Wang、Joji Yui、Qifan Wang、Yiding Zhang、Wakana Mori、Yoko Shimoda、Masayuki Fujinaga、Katsushi Kumata、Tomoteru Yamasaki、Akiko Hatori、Benjamin H. Rotstein、Thomas Lee Collier、Chongzhao Ran、Neil Vasdev、Ming-Rong Zhang、Steven H. Liang

  DOI：10.1021/acschemneuro.5b00248

  日期：2016.1.20

  Fatty acid amide hydrolase (FAAH) is one of the principle enzymes for metabolizing endogenous cannabinoid neurotransmitters such as anandamide, and thus regulates endocannabinoid (eCB) signaling. Selective pharmacological blockade of FAAH has emerged as a potential therapy to discern the endogenous functions of anandamide-mediated eCB pathways in anxiety, pain, and addiction. Quantification of FAAH in the living brain by positron emission tomography (PET) would help our understanding of the endocannabinoid system in these conditions. While most FAAH radiotracers operate by an irreversible ("suicide") binding mechanism, a FAAH tracer with reversibility would facilitate quantitative analysis. We have identified and radiolabeled a reversible FAAH inhibitor, 7-(2-[C-11]methoxyphenyl)-1- (5-(pyridin-2-yl)oxazol-2-yl)heptan-1-one ([C-11]MPPO) in 13% radiochemical yield (nondecay corrected) with >99% radiochemical purity and 2 Ci/mu mol (74 GBq/mu mol) specific activity. The tracer showed moderate brain uptake (0.8 SUV) with heterogeneous brain distribution. However, blocking studies with a potent FAAH inhibitor URB597 demonstrated a low to modest specificity to the target. Measurement of lipophilicity, metabolite, and efflux pathway analysis were also performed to study the pharmacokinetic profile of [C-11]MPPO. In all, we reported an efficient radiolabeling and preliminary evaluation of the first-in-class FAAH inhibitor [C-11]MPPO with alpha-ketoheterocyclic scaffold.
• Pheromone XLI. Stereoselektive Synthesen von 1,5- und 1,6-Alkadienen als Sexualpheromone und Pheromonanaloge
  作者：Hans Jürgen Bestmann、Karl Heinrich Koschatzky、Otto Vostrowsky

  DOI：10.1002/jlac.198219820807

  日期：1982.8.19

  Nach Art eines „Baukastensystems” werden Alkadienylacetate, Alkadienole und Alkadienale, wie sie als Sexualpheromone weiblicher Schmetterlinge bekannt sind, mit ethylen- bzw. trimethylenunterbrochenen Doppelbindungen (1,5- bzw. 1,6-Alkadiene) unterschiedlicher Positionen und Geometrien synthetisiert.

  以“模块化系统”的方式，乙酸二烯基酯，链二烯醇和链二烯醛（它们被称为雌性蝴蝶的性信息素）是通过双键被乙烯或三亚甲基（1,5或1,6链二烯）打断而合成的。位置和几何形状。