[2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-(triphenyl)-phosphonium iodide

• 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: [2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-(triphenyl)-phosphonium iodide
• 英文别名: 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl-triphenylphosphanium;iodide
• 化学式: C₂₅H₂₈O₂P*I
• 分子量: 518.374
• InChiKey: FMRMVFLJFMVVDC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  [2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-(triphenyl)-phosphonium iodide 在 吡啶 、 4-二甲氨基吡啶 、 水 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (E)-1-(tert-Butyl-diphenyl-silanyloxy)-5-(2,6-dichloro-imidazo[1,2-a]pyridin-3-yl)-pent-4-en-2-ol
  参考文献：
  名称：

  Synthesis of the First C3 Ribosylated Imidazo[1,2-a]pyridine C-Nucleoside by Enantioselective Construction of the Ribose Moiety

  摘要：

  The metabolic instability of the glycosidic linkage in 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole prompted us to synthesize the structurally related C-nucleoside 2,6,7-trichloro-3-(beta-D-ribofuranosyl)imidazo[1,2-a]pyridine. Synthesis of this first C3-ribofuranosylimidazo[1,2-a]pyridine was accomplished by developing a modification of existing iodocyclization methodology for obtaining a 1',4'-syn furanosyl precursor, without an extensive protection scheme. This 1',4'-syn precursor was elaborated inter the desired ribofuranosyl C-nucleoside. X-ray crystallography was used to unambiguously determine structure and absolute stereochemistry of this C-nucleoside.

  DOI：

  10.1021/jo9711145
• 作为产物：
  描述：

  4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane 、 三苯基膦 在 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以85%的产率得到[2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-(triphenyl)-phosphonium iodide
  参考文献：
  名称：

  Synthesis of the Eight Enantiomerically Pure Diastereomers of the 12-F₂-Isoprostanes

  摘要：

  Syntheses of the eight enantiomerically pure diastereomers of the 12-F-2-isoprostanes (4-11) are described. The key steps included rhodium-mediated intramolecular cyclopropanation and enzymatic resolution of the racemic diol 12.

  DOI：

  10.1021/ja020816v

文献信息

• Total Synthesis of the Four Enantiomerically Pure Diastereomers of 8-F_2t-Isoprostane
  作者：Douglass F. Taber、Qin Jiang

  DOI：10.1021/jo001731k

  日期：2001.3.1

  Syntheses of the four enantiomerically pure diastereomers of 8-F(2t)-isoprostane (5-8) are described. The key to this approach was to prepare the racemic alcohol 9 in high diastereomeric purity and then resolve 9 by lipase-mediated acetylation to yield the enantiomerically pure alcohols 30 and 32.

  描述了8-F（2t）-异前列腺素（5-8）的四种对映体纯的非对映异构体的合成。该方法的关键是制备高非对映异构纯度的外消旋醇9，然后通过脂肪酶介导的乙酰化作用将9拆分为对映体纯醇30和32。
• Preparation of Ketones from Nitriles and Phosphoranes
  作者：Douglass F. Taber、Lisi Cai

  DOI：10.1021/jo050266u

  日期：2005.6.1

  The preparation of a ketone from a phosphorane and a nitrile is described. The workup conditions are mild, and the yields are high. The unreacted starting materials can easily be recovered.

  描述了由磷烷和腈制备酮的方法。后处理条件温和，产率高。未反应的原料可以容易地回收。
• A stereocontrolled synthesis of anti-2,5-disubstituted tetrahydrofurans
  作者：Sung Ho Kang、Sung Bae Lee

  DOI：10.1016/s0040-4039(00)91973-7

  日期：1993.3

  Anti-2,5-disubstituted tetrahydrofurans, in which one of the substituents is 3′-furanyl group, have been derived from trans-4-(3′-furanyl)-3-buteno

  反式2,5-二取代四氢呋喃（其中一个取代基为3'-呋喃基）已衍生自反式-4-（3'-呋喃基）-3-丁烯
• Stereocontrolled synthesis of 6-epi-D-purpurosamine B by iodocyclocarbamation of a chiral Z-olefin derived from L-alanine and L-malic acid
  作者：Keiji Kamiyama、Yasuharu Urano、Susumu Kobayashi、Masaji Ohno

  DOI：10.1016/s0040-4039(00)96301-9

  日期：——
• Synthesis of the Eight Enantiomerically Pure Diastereomers of the 12-F₂-Isoprostanes
  作者：Douglass F. Taber、Ming Xu、John C. Hartnett

  DOI：10.1021/ja020816v

  日期：2002.11.1

  Syntheses of the eight enantiomerically pure diastereomers of the 12-F-2-isoprostanes (4-11) are described. The key steps included rhodium-mediated intramolecular cyclopropanation and enzymatic resolution of the racemic diol 12.