(R)-5-hydroxy-5-(hydroxymethyl)hexadecanoic acid | 959781-11-4

• 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: (R)-5-hydroxy-5-(hydroxymethyl)hexadecanoic acid
• 英文别名: (5R)-5-hydroxy-5-(hydroxymethyl)hexadecanoic acid
• CAS: 959781-11-4
• 化学式: C₁₇H₃₄O₄
• 分子量: 302.455
• InChiKey: JUQSZYLSJUZCDT-QGZVFWFLSA-N

物化性质

• 熔点：
  76.1-76.4 °C
• 沸点：
  467.1±35.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-5-hydroxy-5-(hydroxymethyl)hexadecanoic acid 在 Amberlyst₁₅ 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以0.312 g的产率得到(+)-tanikolide
  参考文献：
  名称：

  (R)-(+)-Tanikolide 的合成，一种来自海洋蓝藻 Lyngbya majuscula 的有毒和抗真菌 δ-内酯

  摘要：

  (R)-(+)-Tanikolide, a brine-shrimp toxic and antifungal marine metabolite, isolated from the lipid extract of a blue green algae, cyanobacterium, Lyngbia mujuscula, was synthesized starting from (-)-quinic acid.

  DOI：

  10.3987/com-11-12321
• 作为产物：
  描述：

  十三烷醇 在 四氢吡咯 、 4-二甲氨基吡啶 、 Jones reagent 、 草酰氯 、 三氟甲磺酸 、 borane t-butylamine complex 、 palladium on activated carbon 、 水 、 氢气 、 硼酸 、 potassium carbonate 、 对甲苯磺酸 、 二甲基亚砜 、 丙酸 、 甲基磺酰氯 、 三乙胺 、 柠檬酸 、 sodium hydroxide 、 (S)-2-(O-甲基)苯-CBS-恶唑硼烷 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 异丙醇 、 丙酮 、 甲苯 为溶剂， -60.0~45.0 ℃ 、101.33 kPa 条件下， 反应 84.5h， 生成 (R)-5-hydroxy-5-(hydroxymethyl)hexadecanoic acid
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Isoxazolines from Silyl Nitronates

  摘要：

  1,3-Dipolar Cycloadditions of triisopropylsilyl intronates and 2-alkylacroleins produced isoxazolines bearing a chiral quaternary center in high yields-and enantioselectivities with the aid of a chiral oxazaborolidine catalyst. One chiral isoxazoline product was converted to (R)-(+)-Tanikolide in 9 steps in a total yield of 43%.

  DOI：

  10.1021/acs.orglett.5b00826

文献信息

• Concise asymmetric synthesis of (R)-(+)-tanikolide
  作者：Chenxia Zhang、Naoya Hosoda、Masatoshi Asami

  DOI：10.1016/j.tetasy.2007.09.012

  日期：2007.9

  A highly stereoselective total synthesis of (R)-(+)-tanikolide, a delta-lactonic marine natural product, was accomplished in seven steps from easily available starting materials with a 51% overall yield. An asymmetric synthesis of an alpha-hydroxy aldehyde having a stereogenic quaternary center, by the use of (S)-2-(anilinomethyl) pyrrolidine as a chiral auxiliary, was employed in a key step. (c) 2007 Elsevier Ltd. All rights reserved.
• Structural and Synthetic Investigations of Tanikolide Dimer, a SIRT2 Selective Inhibitor, and Tanikolide <i>seco</i>-Acid from the Madagascar Marine Cyanobacterium <i>Lyngbya majuscula</i>
  作者：Marcelino Gutiérrez、Eric H. Andrianasolo、Won Kyo Shin、Douglas E. Goeger、Alexandre Yokochi、Jörg Schemies、Manfred Jung、Dennis France、Susan Cornell-Kennon、Eun Lee、William H. Gerwick

  DOI：10.1021/jo900578j

  日期：2009.8.7

  Tanikolide seco-acid 2 and tanikolide dimer 3, the latter a novel and selective SIRT2 inhibitor, were isolated from the Madagascar marine cyanobacterium Lyngbya majuscula. The structure of 2, isolated as the pure R enantiomer, was elucidated by X-rayexperiment in conjunction with NMR and optical rotation data, whereas the depside molecular structure of 3 was initially thought to be a meso compound as established by NMR, MS, and chiral H PLC analyses. Subsequent total synthesis of the three tanikolide dimer stereoisomers 4, 5, and ent-5, followed by chiral GC-MS comparisons with the natural product, showed it to be exclusively the R,R-isomer 5. Tanikolide dimer 3 (= 5) inhibited SIRT2 with an IC50 = 176 nM in one assay format and 2.4 mu M in another. Stereochemical determination of symmetrical dimers such as compound 3 pose intriguing and subtle questions in structure elucidation and, as shown in the current work, are perhaps best answered in conjunction with total synthesis.
• Sirtuin Modulators as Inhibitors of Cytomegalovirus
  申请人：The Trustees of Princeton University

  公开号：US20160296523A1

  公开（公告）日：2016-10-13

  Agents and methods of inhibiting or improving the growth of viruses are provided.
• Catalytic Asymmetric Synthesis of Isoxazolines from Silyl Nitronates
  作者：Xiaoyu Han、Li Dong、Caiwei Geng、Peng Jiao

  DOI：10.1021/acs.orglett.5b00826

  日期：2015.7.2

  1,3-Dipolar Cycloadditions of triisopropylsilyl intronates and 2-alkylacroleins produced isoxazolines bearing a chiral quaternary center in high yields-and enantioselectivities with the aid of a chiral oxazaborolidine catalyst. One chiral isoxazoline product was converted to (R)-(+)-Tanikolide in 9 steps in a total yield of 43%.
• Synthesis of (R)-(+)-Tanikolide, a Toxic and Antifungal δ-Lactone from the Marine Cyanobacterium Lyngbya majuscula
  作者：Keizo Matsuo、Junko Hikita、Keiji Nishiwaki

  DOI：10.3987/com-11-12321

  日期：——

  (R)-(+)-Tanikolide, a brine-shrimp toxic and antifungal marine metabolite, isolated from the lipid extract of a blue green algae, cyanobacterium, Lyngbia mujuscula, was synthesized starting from (-)-quinic acid.