(R)-5-methyl-3-phenylthio-3H-dihydrofuran-2-one | 628687-61-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (R)-5-methyl-3-phenylthio-3H-dihydrofuran-2-one
• 英文别名: (5R)-5-methyl-3-phenylsulfanyloxolan-2-one
• CAS: 628687-61-6
• 化学式: C₁₁H₁₂O₂S
• 分子量: 208.281
• InChiKey: BFJMPYZVXRHURN-HNHGDDPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-5-methyl-3-phenylthio-3H-dihydrofuran-2-one 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 26.5h， 生成 (5R)-3-[(S)-13-hydroxy-13-((S)-5-oxotetrahydrofuran-2-yl)tridec-6-en-8-ynyl]-5-methyl-3-(phenylsulfanyl)dihydrofuran-2-one
  参考文献：
  名称：

  Design, syntheses, and biological evaluations of squamostolide and its related analogs

  摘要：

  Squamostolide and its related analogs were designed and synthesized for biological evaluation. All these compounds were tested for growth inhibition activities against human tumor cell lines, in which one of the compounds showed the most potent cyto-toxicity among these derivatives against a full panel of 60 human cancer cell lines. The same compound also showed G2/M phase arrest and a weak apoptotic effect during flow cytometric analysis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.050
• 作为产物：
  描述：

  (R)-5-甲基二氢呋喃-2-酮 、 二苯二硫醚 在 lithium diisopropyl amide 作用下， 反应 3.0h， 生成 (R)-5-methyl-3-phenylthio-3H-dihydrofuran-2-one
  参考文献：
  名称：

  Synthesis of (15S,16S,21R)-4-deoxyrollicosin analog

  摘要：

  Synthesis of 4-deoxy rollicosin analog 2 was completed in nine steps, which was based on palladium-catalyzed coupling of two building blocks 3 and 4. Lactone 3 was synthesized from 5-hexyn-1-ol, and vinyl iodide 4 was accessed from L-glutamate and 1-hexyne. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.088

文献信息

• Stereostructural studies on the 4-hydroxylated annonaceous acetogenins: Synthesis of model butenolides of known relative and absolute configuration involving an intriguing translactonization reaction
  作者：Thomas R. Hoye、Paul R. Hanson、Linda E. Hasenwinkel、Elizabeth A. Ramirez、Zhiping Zhuang

  DOI：10.1016/s0040-4039(00)78427-9

  日期：1994.11

  Each diastereomer of model butenolides 3 was synthesized from appropriate antipodes of two propylene oxide molecules. Concomitant translactonization reactions have important stereochemical ramifications.
• Total Synthesis of (+)-<i>cis</i>-Sylvaticin:  Double Oxidative Cyclization Reactions Catalyzed by Osmium
  作者：Timothy J. Donohoe、Robert M. Harris、Jeremy Burrows、Jeremy Parker

  DOI：10.1021/ja0660148

  日期：2006.10.1

  The double oxidative cyclization of dienes is a viable procedure for making complex natural products containing cis-THF units. A double deprotection/double oxidative cyclization strategy using catalytic osmium tetroxide was used to construct the bisheterocyclic core of cis-sylvaticin and ultimately confirm its structure. The natural product was then prepared by a short sequence of reactions that is exceptionally concise: the final route being just 13 linear steps and 19 chemical operations in total.