(4S)-2-(4-methoxyphenyl)-4-methyl-1,3-dioxolane-4-carbaldehyde | 1179989-36-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4S)-2-(4-methoxyphenyl)-4-methyl-1,3-dioxolane-4-carbaldehyde
• CAS: 1179989-36-6
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: HZNMEOGJQBKKAF-PIJUOVFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-2-(4-methoxyphenyl)-4-methyl-1,3-dioxolane-4-carbaldehyde 在 四(三苯基膦)钯 、 三正丁基氢锡 、 四氯化锡 、 二异丁基氢化铝 、 碳酸氢钠 、 potassium carbonate 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 8.25h， 生成 (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：

  在 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成 (4S)-2-(4-methoxyphenyl)-4-methyl-1,3-dioxolane-4-carbaldehyde
  参考文献：
  名称：

  立体选择性合成iriomoteolide-1a半缩酮核心

  摘要：

  立体选择性合成的iriometeolide-1a（1）的环状半基因核心。关键步骤涉及烯丙基硅烷4和醛5的Sakurai反应，该醛具有手性α-叔中心。β，γ-不饱和酮23的轻度TES脱保护导致伴随的环化反应，以产生完全完整的半缩酮核心2。

  DOI：

  10.1016/j.tetlet.2009.05.092

文献信息

• Stereoselective synthesis of iriomoteolide-1a hemiketal core
  作者：Jun Xie、David A. Horne

  DOI：10.1016/j.tetlet.2009.05.092

  日期：2009.8

  A stereoselective synthesis of the cyclic hemiketal core of iriometeolide-1a (1) is described. The key step involves a Sakurai reaction of allylsilane 4 and aldehyde 5, which bears a chiral α-tertiary center. Mild TES deprotection of β,γ-unsaturated ketone 23 led to concomitant cyclization to produce the fully intact hemiketal core 2.

  立体选择性合成的iriometeolide-1a（1）的环状半基因核心。关键步骤涉及烯丙基硅烷4和醛5的Sakurai反应，该醛具有手性α-叔中心。β，γ-不饱和酮23的轻度TES脱保护导致伴随的环化反应，以产生完全完整的半缩酮核心2。
• 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.