(2R,4S,5R)-5-allyl-2-(4-methoxyphenyl)-4-methyl-1,3-dioxane | 1192350-59-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,4S,5R)-5-allyl-2-(4-methoxyphenyl)-4-methyl-1,3-dioxane
• 英文别名: (2R,4S,5R)-2-(4-methoxyphenyl)-4-methyl-5-prop-2-enyl-1,3-dioxane
• CAS: 1192350-59-6
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: ZROUFGDMRUUJHF-NJZAAPMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R)-5-allyl-2-(4-methoxyphenyl)-4-methyl-1,3-dioxane 在 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 pyridine hydrofluoride 、 叔丁基锂 、 二异丁基氢化铝 、 臭氧 、 三乙胺 、 8-甲氧基-9-硼杂双环[3.3.1]壬烷 、 sodium iodide 、 双环己基(三氟甲烷磺酰氧基)硼烷 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 丙酮 、 甲苯 、 正戊烷 为溶剂， 反应 58.33h， 生成 (2S,3S,5R,6S,10R,15S,E)-11-((tert-butyldimethylsilyl)oxy)-2,15-bis((4-methoxybenzyl)oxy)-3,6,10-trimethyl-13-methylene-10-((triethylsilyl)oxy)octadeca-8,17-dien-5-ol
  参考文献：
  名称：

  Total synthesis of the proposed structure of iriomoteolide-1a

  摘要：

  Full details of the total synthesis of the proposed structure of iriomoteolide-1a (1) are described. The key steps include (i) a Sakurai reaction between allylsilane 11 and aldehyde 10 that bears both a tertiary chiral center and vinyl iodide moiety (ii) an anti-aldol reaction to construct the C18/C19 chiral centers (iii) a B-alkyl Suzuki-Miyaura coupling reaction to assemble the C7-C23 fragment, and (iv) a macrocyclic ring-closing metathesis to complete the construction of the target molecule. Two different approaches to access penultimate precursor 2 are delineated. The NMR spectra of the synthetic iriomoteolide-1a (1) were found not to match those reported for the natural product bringing into question its true structural identity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.066
• 作为产物：
  描述：

  4-甲氧基苯甲醛二甲缩醛 、 (2R,3S)-2-allylbutane-1,3-diol 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 以262 mg的产率得到(2R,4S,5R)-5-allyl-2-(4-methoxyphenyl)-4-methyl-1,3-dioxane
  参考文献：
  名称：

  Asymmetric Synthesis of the C(7)−C(23) Fragment of Iriomoteolide-1a

  摘要：

  An efficient synthesis of the C(7)-C(23) fragment 2 of iriomoteolide-1a (1) has been accomplished via a B-alkyl Suzuki-Miyaura cross-coupling reaction followed by deprotection and cyclization to form the cyclic hemiketal core.

  DOI：

  10.1021/ol902110a

文献信息

• Asymmetric Synthesis of the C(7)−C(23) Fragment of Iriomoteolide-1a
  作者：Jun Xie、Yuelong Ma、David A Horne

  DOI：10.1021/ol902110a

  日期：2009.11.5

  An efficient synthesis of the C(7)-C(23) fragment 2 of iriomoteolide-1a (1) has been accomplished via a B-alkyl Suzuki-Miyaura cross-coupling reaction followed by deprotection and cyclization to form the cyclic hemiketal core.
• Total synthesis of the proposed structure of iriomoteolide-1a
  作者：Jun Xie、Yuelong Ma、David A. Horne

  DOI：10.1016/j.tet.2011.07.066

  日期：2011.9

  Full details of the total synthesis of the proposed structure of iriomoteolide-1a (1) are described. The key steps include (i) a Sakurai reaction between allylsilane 11 and aldehyde 10 that bears both a tertiary chiral center and vinyl iodide moiety (ii) an anti-aldol reaction to construct the C18/C19 chiral centers (iii) a B-alkyl Suzuki-Miyaura coupling reaction to assemble the C7-C23 fragment, and (iv) a macrocyclic ring-closing metathesis to complete the construction of the target molecule. Two different approaches to access penultimate precursor 2 are delineated. The NMR spectra of the synthetic iriomoteolide-1a (1) were found not to match those reported for the natural product bringing into question its true structural identity. (C) 2011 Elsevier Ltd. All rights reserved.