(3-hydroxypropyl)triphenylphosphonium iodide | 14580-95-1

• 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: (3-hydroxypropyl)triphenylphosphonium iodide
• 英文别名: 3-hydroxypropyl(triphenyl)phosphanium;iodide
• CAS: 14580-95-1
• 化学式: C₂₁H₂₂OP*I
• 分子量: 448.283
• InChiKey: HTPPTFDKMMKCIQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.37
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-hydroxypropyl)triphenylphosphonium iodide 在 氢氧化钾 作用下， 生成 3-(diphenylphosphinoyl)-1-propanol
  参考文献：
  名称：

  2,2,2-三苯基-1,2-氧杂磷（V）olan和-氧杂ars（V）olan

  摘要：

  由3-羟丙基三苯基碘化prepared制备2,2,2-三苯基-1，2-氧杂磷（V）olan，并将其在300°重排为3-苯氧基丙基二苯基膦。由相应的son盐制备了2,2,2-三苯基-1，2-氧杂芳基（V）olan，并在160–180°下得到了三苯基ar和烯丙醇。给出了标题化合物的核磁共振谱。

  DOI：

  10.1039/j39670001099
• 作为产物：
  描述：

  3-碘丙醇 、 三苯基膦 以 苯 为溶剂， 生成 (3-hydroxypropyl)triphenylphosphonium iodide
  参考文献：
  名称：

  2,2,2-三苯基-1,2-氧杂磷（V）olan和-氧杂ars（V）olan

  摘要：

  由3-羟丙基三苯基碘化prepared制备2,2,2-三苯基-1，2-氧杂磷（V）olan，并将其在300°重排为3-苯氧基丙基二苯基膦。由相应的son盐制备了2,2,2-三苯基-1，2-氧杂芳基（V）olan，并在160–180°下得到了三苯基ar和烯丙醇。给出了标题化合物的核磁共振谱。

  DOI：

  10.1039/j39670001099

文献信息

• Total Synthesis of the Marine Alkaloids (−)-Lepadins A, B, and C Based on Stereocontrolled Intramolecular Acylnitroso-Diels−Alder Reaction
  作者：Tetsuji Ozawa、Sakae Aoyagi、Chihiro Kibayashi

  DOI：10.1021/jo001589n

  日期：2001.5.1

  The first syntheses of (-)-lepadins A and C, as well as a new synthesis of (-)-lepadin B, have been achieved from commercially available (S)-malic acid. The methodology is based on an intramolecular hetero-Diels--Alder reaction of the acylnitroso compound, affording the bicyclic oxazino lactam with trans selectivity, which was converted to the cis-decahydroquinoline via asymmetric enolate hydroxylation

  （-）-lepadins A和C的第一个合成，以及（-）-lepadin B的新合成，已经从市售（S）-苹果酸中获得。该方法基于酰基亚硝基化合物的分子内杂Diels-Alder反应，可提供具有反式选择性的双环恶嗪内酰胺，可通过不对称烯醇化羟基化反应随后转化为顺式十氢喹啉，然后进行分子内羟醛环化反应。通过使用带有（E）-碘链烯基的顺式十氢喹啉作为共同的关键中间体进行总合成，该中间体通过钯催化的Suzuki交叉偶联反应与（E）-己烯基单元进行收敛偶联，以精制C5位置的辛二烯基侧链。
• A novel reaction of oxaphosphoranes leading to 7-membered cyclic vinylidene acetals
  作者：Kentaro Okuma、Yuichiro Tanaka、Hiroshi Ohta

  DOI：10.1016/s0040-4039(00)60536-1

  日期：1993.6

  Reaction of oxaphosphoranes with paraformaldehyde yielded novel 7-membered cyclic vinylidene acetals in almost quantitative yield. Phosphonium betaines reacted with parformaldehyde to give new betaines, which further reacted with paraformaldehyde to afford olefins via Wittig reaction.

  草酰膦与低聚甲醛的反应以几乎定量的产率产生了新型的7元环亚乙烯基缩醛。be甜菜碱与多聚甲醛反应生成新的甜菜碱，再与多聚甲醛反应通过Wittig反应生成烯烃。
• Samarium(II) Iodide-Mediated Reductive Annulations of Ketones Bearing a Distal Vinyl Epoxide Moiety
  作者：Gary A. Molander、Sagar R. Shakya

  DOI：10.1021/jo960335s

  日期：1996.1.1

  Samarium(II) iodide in the presence of hexamethylphosphoramide (HMPA) efficiently promotes the intramolecular coupling of ketones with distal epoxy olefins. The reaction appears to proceed by a mechanism wherein a ketyl couples with the unsaturated epoxide. Subsequent fragmentation of the epoxide ring in compounds 1a-k yields carbocycles 2a-k with an allyl alcohol side chain in good yields, and often with high diastereoselectivity. When tetramethylguanidine was used as an additive instead of HMPA, the desired carbocycle was obtained in good yield, but the diastereoselectivity was diminished. A palladium(0)-catalyzed SmI2 reaction provided the expected product in modest yield, but the sense of diastereoselectivity was reversed. In the latter case, a different reaction mechanism may be involved. Thus, formation of an allylsamarium species may be invoked, with nucleophilic carbonyl addition leading to the observed facial selectivity.
• Jo Davisson; Neal, Timothy R.; Dale Poulter, Journal of the American Chemical Society, 1993, vol. 115, # 4, p. 1235 - 1245
  作者：Jo Davisson、Neal, Timothy R.、Dale Poulter

  DOI：——

  日期：——
• Lewis Acid Promoted Prins Cyclization Using Non-Conjugated Diene Alcohol: Sequential Reactions Terminated by Fluoride Ion
  作者：Kouichi Matsumoto、Rina Yanagi、Kouji Yamaguchi、Erin Hayashi、Eri Yasuda、Toshiki Nokami、Keiji Nishiwaki、Shigenori Kashimura、Kaho Kuriyama

  DOI：10.3987/com-18-13940

  日期：——

  The sequential cyclization involving Prins cyclization was successfully demonstrated, in which the various aldehydes bearing the alkyl or aromatic substituent were reacted with the alcohol bearing the non-conjugated diene moiety in the presence of 2 equiv. of BF3 center dot Et2O and 4 mol% of TMSC1 at -40 degrees C to afford the corresponding fluorinated bicyclic compounds in moderate to good yields.