<9-((tetrahydro-2H-pyran-2-yl)oxy)nonyl>triphenylphosphonium bromide | 55695-91-5

• 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: <9-((tetrahydro-2H-pyran-2-yl)oxy)nonyl>triphenylphosphonium bromide
• 英文别名: <9-(tetrahydro-2H-pyran-2-yloxy)nonyl>triphenylphosphonium bromide；<9-(Tetrahydro-2-pyranyloxy)nonyl>-triphenylphosphonium-bromid；<9-(Tetrahydro-2-pyranyloxy)nonyl>triphenylphosphoniumbromid；9-(2-tetrahydropyranyl)oxynon-1-yltriphenylphosphonium bromide；1-tetrahydropyranyloxynonyl-9-triphenylphosphonium bromide；9-tetrahydropyranyloxynonyl triphenylphosphonium bromide；9-(Oxan-2-yloxy)nonyl-triphenylphosphanium;bromide
• CAS: 55695-91-5
• 化学式: Br*C₃₂H₄₂O₂P
• 分子量: 569.562
• InChiKey: HOOMCOVESYBDRF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  <9-((tetrahydro-2H-pyran-2-yl)oxy)nonyl>triphenylphosphonium bromide 在 咪唑 、 sodium azide 、 四丁基氟化铵 、 碘 、 二甲基氯化铝 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 109.5h， 生成 methyl (5S,6E,8Z,11Z)-20-amino-5-[tert-butyl(diphenyl)silyl]oxyicosa-6,8,11-trienoate
  参考文献：
  名称：

  The synthesis of a 5-HETE photoaffinity ligand

  摘要：

  The design and synthesis of a photoaffinity ligand 26, targeted at the 5h-dh, was accomplished. The synthesis was effected by two new synthetic routes which focus on the omega-hydroxy 5-HETE derivative 12 as a pivotal synthon. Preliminary results show ligand 26 to be an excellent substrate for the 5h-dh. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01064-9
• 作为产物：
  描述：

  9-溴-1-壬醇 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 19.33h， 生成 <9-((tetrahydro-2H-pyran-2-yl)oxy)nonyl>triphenylphosphonium bromide
  参考文献：
  名称：

  Potent Oligomerization and Macrocyclization Activity of the Thioesterase Domain of Vicenistatin Polyketide Synthase

  摘要：

  The thioesterase domain of the polyketide synthase involved in the biosynthesis of the 20-membered macrolactam antibiotic vicenistatin (VinTE) was found to catalyze oligomerization and macrocyclization of omega-hydroxy fatty acid ethyl esters to afford 17-28-membered macrocyclic lactones. The ring sizes of the macrocycles appear to be limited to the more moderate sizes because of the space limitation of the active site of VinTE. It was also verified that the initially formed linear dimer is first released from the active site of VinTE and then is recognized again by VinTE prior to its transformation to the cyclic dimer.

  DOI：

  10.1055/s-0031-1290385

文献信息

• The synthesis of (11R,12S)-lactobacillic acid and its enantiomer
  作者：Geoffrey D. Coxon、Juma R. Al-Dulayymi、Mark S. Baird、Stefan Knobl、Evan Roberts、David E. Minnikin

  DOI：10.1016/s0957-4166(03)00165-4

  日期：2003.5

  (11R,12S)-Lactobacillic acid has been prepared from 2,3-O-isopropylidene-D-glyceraldehyde, in a sequence involving asymmetric cyclopropanation, and from cis-cyclopropane-1,2-dimethanol, using enzymatic desymmetrisation. The key step in the former route was the stereochemically controlled cyclopropanation of (1Z,4'S)-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-octene via a Simmons-Smith type reaction, using diethylzinc and chloroiodomethane. This product was converted into the key intermediate (1R,2S)-1-formyl-2-hexylcyclopropane, which was also obtained by a known sequence from the (1R,2S)-monobutyrate ester of cis-cyclopropane-1,2-dimethanol. This pivotal aldehyde was converted into (11R,12S)-lactobacillic acid. Using analogous chemistry, the (11S,12R)-enantiomer of lactobacillic acid was prepared from 2,3-O-isopropylidene-D-glyceraldehyde or from the (1S,R)-monobutyrate ester of cis-cyclopropane-1,2-dimethanol. (C) 2003 Elsevier Science Ltd. All rights reserved.

  (LS,12S)-乳酸杆菌酸已从2,3-O异丙烯基-D-甘油醛中制备，其中涉及非对映异构物环丙烷化，以及从顺式环丙烷-1,2-二甲醇中使用酶催化去对称化。前一条路线的关键步骤是通过对(1Z,4S')-(2',2'-二甲基-1',3'-二氧杂环戊烷-4'-基)-1-辛烯进行Simmons-Smith型反应进行立体化学控制的环丙烷化，使用了二乙基锌和碘氯甲烷。该产品被转化为关键中间体(1R,2S)-1-甲酰基-2-己基环丙烷，该中间体也可通过已知路线从顺式环丙烷-1,2-二甲醇的(1R,2S)-单丁酸酯获得。这种关键的醛被转化为(11R,12S)-乳酸杆菌酸。通过类似化学，乳酸杆菌酸的(11S,12R)-对映异构体从2,3-O异丙烯基-D-甘油醛或顺式环丙烷-1,2-二甲醇的(1S,R)-单丁酸酯中制备。 (C) 2003 Elsevier Science Ltd. 保留所有权利。
• The synthesis of both enantiomers of lactobacillic acid and mycolic acid analogues
  作者：Geoffrey D. Coxon、Stefan Knobl、Evan Roberts、Mark S. Baird、Juma R. Al Dulayymi、Gurdyal S. Besra、Patrick J. Brennan、David E. Minnikin

  DOI：10.1016/s0040-4039(99)01378-7

  日期：1999.9

  cis-cyclopropane-1, 2-dimethanol by enzymatic desymmetrisation. The syntheses of (11S 12R)-lactobacillic acid (2) and (1R, 2S) 1-(3′-methoxycarbonylpropyl)-2-octadecylcyclopropane (26) and related analogues (27 and 28) have also been achieved.

  （11 R，12 S）-乳酸核糖酸（1）已经通过不对称环丙烷化由D-甘露糖醇或通过酶促不对称化从顺式-环丙烷-1、2-二甲醇制备。还已经合成了（11 S 12 R）-乳酸杆菌酸（2）和（1 R，2 S）1-（3'-甲氧基羰基丙基）-2-十八烷基环丙烷（26）及其相关类似物（27和28）。 。
• 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 of Unique Ceramides and Cerebrosides Occurring in Human Epidermis
  作者：Siliva Müller、Richard R. Schmidt

  DOI：10.1002/hlca.19930760141

  日期：1993.2.10

  The sphingolipids 1a, b and 2a, b which play important roles in epidermal barrier function, were synthesized by N-acylation of C18-sphingosine 3 and 1-O-glucosylated C18-sphingosine 6, respectively, with ω-acyloxy-substituted fatty acids 4 and 5 (Scheme 1). These fatty acids were obtained from ω-hydroxy-substituted fatty acids 8 and 9 by esterification with linoleic acid (7). The C34-fatty acid 8 was

  在表皮屏障功能中起重要作用的鞘脂1a，b和2a，b通过分别用ω-酰氧基取代的C 18-鞘氨醇3和1- O-葡萄糖基化的C 18-鞘氨醇6进行N-酰化来合成脂肪酸4和5（方案1）。这些脂肪酸通过用亚油酸（7）酯化而从ω-羟基取代的脂肪酸8和9获得。C 34-脂肪酸如下制备图8：通过C 13-醛13与C 12 -on盐15或C 12-醛24与C 13 -on盐21的维蒂希反应分别得到C 25-化合物18，和随后氢化和O-脱保护（方案2）。或者，通过铜催化将C 13烷基卤化物19与格氏试剂偶联，通过30制备8。衍生自C 12烷基溴化物14的试剂（方案2）。在O-脱保护后（方案3），将18氧化为醛39并与C 9 -phosph盐41进行Wittig反应，得到了所需的ω-羟基取代的脂肪酸8。类似地，维悌希的C反应11 -鏻盐22为C 12 -醛24布置Ç 23 -醛40，氢化后，ö-脱保护和氧化；与
• Synthesis of dienic fluorinated analogs of insect sex pheromones
  作者：Francisco Camps、Jose Coll、Gemma Fabrias、Angel Guerrero

  DOI：10.1016/s0040-4020(01)91296-7

  日期：1984.1

  Synthesis of fluorinated analogs of some dienic insect sex pherormones through a stereocontrolled Wittig reaction of β-fluorinated aldehydes with the appropriate ω-functionalized ylides is reported. Some features of the 1H and 19F NMR spectra of these analogs are also discussed.

  据报道，通过β-氟化醛与适当的ω-官能化的乙炔的立体控制的Wittig反应，合成了一些二齿昆虫性信息素的氟化类似物。还讨论了这些类似物的1 H和19 F NMR光谱的某些特征。