(E,2R)-4-iodo-2-[(4-methoxyphenyl)methoxy]-2-methylbut-3-enal | 1334288-77-5

• 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: (E,2R)-4-iodo-2-[(4-methoxyphenyl)methoxy]-2-methylbut-3-enal
• CAS: 1334288-77-5
• 化学式: C₁₃H₁₅IO₃
• 分子量: 346.165
• InChiKey: FJKSRYXHYUHGKY-SBDDDAINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  triethyl-[(4S)-2-(trimethylsilylmethyl)hepta-1,6-dien-4-yl]oxysilane 、 (E,2R)-4-iodo-2-[(4-methoxyphenyl)methoxy]-2-methylbut-3-enal 在 四氯化锡 、 水 、 碳酸氢钠 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.75h， 以20 mg的产率得到(1E,3R,8S)-1-iodo-3-[(4-methoxyphenyl)methoxy]-3-methyl-6-methylidene-8-triethylsilyloxyundeca-1,10-dien-4-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：

  (4R)-4-ethynyl-2-(4-methoxyphenyl)-4-methyl-1,3-dioxolane 在 四(三苯基膦)钯 、 三正丁基氢锡 、 二异丁基氢化铝 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.33h， 生成 (E,2R)-4-iodo-2-[(4-methoxyphenyl)methoxy]-2-methylbut-3-enal
  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