(5R,7S)-7-hydroxy-5,8,8-trimethylnonanoic acid | 1403236-02-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (5R,7S)-7-hydroxy-5,8,8-trimethylnonanoic acid
• CAS: 1403236-02-1
• 化学式: C₁₂H₂₄O₃
• 分子量: 216.321
• InChiKey: GLASNUGKTGDSHX-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R,7S)-7-hydroxy-5,8,8-trimethylnonanoic acid 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 ammonium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.5h， 以0.204 mmol的产率得到(5R,7S)-7-hydroxy-5,8,8-trimethylnonanamide
  参考文献：
  名称：

  Enantioselective Redox-Neutral Coupling of Aldehydes and Alkenes by an Iron-Catalyzed “Catch–Release” Tethering Approach

  摘要：

  The reductive coupling of aldehydes and alkenes is an emerging technology that holds the potential to reinvent carbonyl addition chemistry. However, existing enantioselective methods are limited to form "branched" products. Herein, we present a directed enantio- and diastereoselective alkylation of aldehydes with simple olefins to selectively yield linear coupling products. This is achieved by redox-neutral remote functionalization, whereby a tethering "catch-release" strategy decisively solves the key problems of reactivity and selectivity.

  DOI：

  10.1021/jacs.8b12242
• 作为产物：
  描述：

  (6R,8S)-8-hydroxy-6,9,9-trimethyldecan-2-one 在 碘 、 potassium iodide 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 生成 (5R,7S)-7-hydroxy-5,8,8-trimethylnonanoic acid
  参考文献：
  名称：

  Enantioselective Redox-Neutral Coupling of Aldehydes and Alkenes by an Iron-Catalyzed “Catch–Release” Tethering Approach

  摘要：

  The reductive coupling of aldehydes and alkenes is an emerging technology that holds the potential to reinvent carbonyl addition chemistry. However, existing enantioselective methods are limited to form "branched" products. Herein, we present a directed enantio- and diastereoselective alkylation of aldehydes with simple olefins to selectively yield linear coupling products. This is achieved by redox-neutral remote functionalization, whereby a tethering "catch-release" strategy decisively solves the key problems of reactivity and selectivity.

  DOI：

  10.1021/jacs.8b12242

文献信息

• Evolution of a Protecting-Group-Free Total Synthesis: Studies en Route to the Neuroactive Marine Macrolide (−)-Palmyrolide A
  作者：Rodolfo Tello-Aburto、Tara D. Newar、William A. Maio

  DOI：10.1021/jo301121f

  日期：2012.7.20

  neuroactive marine macrolide (−)-palmyrolide A is described. Our first-generation approach aimed to unlock the unknown C(5)–C(7) stereochemical relationship via the synthesis of four diastereomers of palmyrolide A aldehyde, a known degradation product. When these efforts provided inconclusive results, recourse to synthesizing all possible stereocombinations of the 15-membered macrolide was undertaken.

  描述了我们对神经活性海洋大环内酯（-）-palmyrolide A的第一个全合成的合成工作的完整说明。我们的第一代方法旨在通过合成已知的降解产物Palmyrolide A醛的四种非对映异构体来解锁未知的C（5）-C（7）立体化学关系。当这些努力提供不确定的结果时，便采取了合成15元大环内酯类化合物所有可能的立体组合的方法。这些研究对于确认绝对立体化学至关重要，可以产生第一个（+）- ent- palmyrolide A的全合成。在这项工作之后，还报道了第一个无保护基的天然（-）-palmyrolide A的全合成。 。
• Total Synthesis of the Macrocyclic <i>N</i>-Methyl Enamides Palmyrolide A and 2<i>S</i>-Sanctolide A
  作者：Andrew D. Wadsworth、Daniel P. Furkert、Margaret A. Brimble

  DOI：10.1021/jo502238r

  日期：2014.11.21

  details of the total syntheses of the initially reported and revised structures of the neuroprotective agent palmyrolide A are reported. The key macrocyclization step was achieved using a sequential ring-closing metathesis/olefin isomerization reaction. Furthermore, the total synthesis of the related macrolide (2S)-sanctolide A is reported. The synthesis used key elements from the synthesis of palmyrolide

  报道了神经保护剂棕榈酰吡咯烷酮A的最初报道和修改的结构的全部合成的全部细节。关键的大环化步骤是使用顺序的闭环复分解/烯烃异构化反应实现的。此外，已经报道了相关的大环内酯（2S）-三萜内酯A的全合成。合成过程中使用了棕榈油酸酯A合成中的关键元素，包括RCM /烯烃异构化序列。本文所述的合成工作用于促进天然产物Sanctolide A的立体化学分配，并证明了该方法在合成大环叔烯酰胺天然产物中的效用。
• Total Synthesis of the Initially Reported and Revised Structures of the Neuroprotective Agent Palmyrolide A
  作者：Andrew D. Wadsworth、Daniel P. Furkert、Jonathan Sperry、Margaret A. Brimble

  DOI：10.1021/ol3025956

  日期：2012.10.19

  neuroprotective agent palmyrolide A are reported. The key macrocyclization step was achieved using a sequential ring closing metathesis/olefin isomerization reaction. The synthetic work described herein serves to confirm the recent structural revision of this unusual natural product.

  报道了神经保护剂棕榈酰吡咯烷酮A的最初报道的和修饰的结构的总合成。关键的大环化步骤是使用顺序的闭环复分解/烯烃异构化反应实现的。本文所述的合成工作用于证实这种不寻常的天然产物的最新结构变化。