((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-furan-3-yl-methanone | 194476-01-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-furan-3-yl-methanone
• 英文别名: [(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-(furan-3-yl)methanone
• CAS: 194476-01-2
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: XSKBAGBUSJXWSQ-MRVPVSSYSA-N

物化性质

• 熔点：
  35-36 °C
• 沸点：
  271.0±40.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-furan-3-yl-methanone 在 过氧乙酸 、 4-二甲氨基吡啶 、 正丁基锂 、 sodium acetate 、 三乙基硼氢化锂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 3-[(R)-[tert-butyl(dimethyl)silyl]oxy-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2H-furan-5-one
  参考文献：
  名称：

  Total Syntheses of Sphydrofuran, Secosyrins, and Syributins^,1

  摘要：

  Two groups of natural products, sphydrofuran (1) and its furan derivative (2) and secosyrins 1 and 2 (3a, 3b) and syributins 1 and 2 (4a, 4b), were synthesized from one precursor (6), which was realized starting from 3-tri-n-butylstannylfuran or 3-bromofuran.

  DOI：

  10.1021/jo970476+
• 作为产物：
  描述：

  (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 重铬酸吡啶 、 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 ((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-furan-3-yl-methanone
  参考文献：
  名称：

  Total Syntheses of Sphydrofuran, Secosyrins, and Syributins^,1

  摘要：

  Two groups of natural products, sphydrofuran (1) and its furan derivative (2) and secosyrins 1 and 2 (3a, 3b) and syributins 1 and 2 (4a, 4b), were synthesized from one precursor (6), which was realized starting from 3-tri-n-butylstannylfuran or 3-bromofuran.

  DOI：

  10.1021/jo970476+

文献信息

• Total Synthesis of Plakortone B
  作者：Xin-Gang Xie、Xun-Wei Wu、Hing-Ken Lee、Xiao-Shui Peng、Henry N. C. Wong

  DOI：10.1002/chem.201000189

  日期：——

  Plakortone B is a naturally occurring bicyclic[3.3.0]furanolactone compound with attractive bioactivities. Although the relative configuration of plakortone B’s central core had been established by NMR spectroscopic methods, the absolute configuration of its four stereocenters remained unknown. In the present paper, all four possible isomers of plakortone B were synthesized and one of these molecules

  Plakortone B是一种具有吸引力的生物活性的天然存在的双环[3.3.0]呋喃内酯化合物。尽管已通过NMR光谱法确定了plakortone B中央核的相对构型，但其四个立体中心的绝对构型仍然未知。在本文中，合成了九个苦参酮B的所有四种可能的异构体，并且根据1 H，13 C NMR光谱和比旋光度的比较，发现其中一个分子与天然的九个苦参酮B相同。因此，确定天然普拉克酮B的绝对构型为（3 S，4 S，6 R，10 R）。
• On the diastereocontrol in the formation of (2R,3S)-3-(3′-furyl)-1,2-O-isopropylidenedioxy-3-pentanol and its (2R,3R)-diastereomer
  作者：Chi Wai Hui、Hing Ken Lee、Henry N.C Wong

  DOI：10.1016/s0040-4039(01)02055-x

  日期：2002.1

  The two enantiomeric bicyclic lactone skeletons of the marine natural products plakortones, whose absolute configuration are yet unknown, are approachable from (2R,3S)-3-(3'-furyl)-1,2-O-isopropylidenedioxy-3-pentanol 1a and its (2R,3R)-diastereomer 1b. To obtain these optically pure diastereomers, two pathways were studied, in which different solvents, additives and nucleophilic reagents were employed. The stereochemistry was successfully controlled in the reaction or (2R)-1,2-O-isopropylidenedioxy-3-pentanone 3 with 3-furyllithium, which gave high syn-selectivity in Et2O. but excellent anti-selectivity in toluene. (C) 2001 Elsevier Science Ltd. All rights reserved.