6-(1,2-二羟基戊基)-4-甲氧基-5,6-二氢吡喃-2-酮 | 41164-59-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 6-(1,2-二羟基戊基)-4-甲氧基-5,6-二氢吡喃-2-酮
• 英文名称: 6S-(1'S,2'R-dihydroxypentyl)-4-methoxy-5,6-dihydropyran-2-one, LL-P88pβ
• 英文别名: (6S,1'S,2'R)-6-(1',2'-Dihydroxypentyl)-5,6-dihydro-4-methoxypyrane-2-one；(S)-6-((1S,2R)-1,2-dihydroxypentyl)-4-methoxy-5,6-dihydro-2H-pyran-2-one；hydroxypestalotin；(6S,1’S,2’R)-LL-P880β；(6S,1'S,2'R)-hydroxypestalotin；(6S,1'S,2'R)-LL-P880β；7-Hydroxypestalotin；(2S)-2-[(1S,2R)-1,2-dihydroxypentyl]-4-methoxy-2,3-dihydropyran-6-one
• CAS: 41164-59-4
• 化学式: C₁₁H₁₈O₅
• 分子量: 230.261
• InChiKey: YLHOHANRUSKHKO-YWVKMMECSA-N

物化性质

• 熔点：
  133-134 °C
• 沸点：
  456.7±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  6-(1,2-二羟基戊基)-4-甲氧基-5,6-二氢吡喃-2-酮 以 甲醇 为溶剂， 反应 24.0h， 以0.2 mg的产率得到pestalrone A
  参考文献：
  名称：

  Polyketides from Pestalotiopsis zonata and structure revision of pestalrones A and B

  摘要：

  The structures of pestalrones A-B were revised via reinterpretation of the NMR data and a brief chemical transformation from the co-occurring polyketides, in our investigation on the secondary metabolites of Pestalotiopsis zonata, which also afforded a new alpha-pyrone derivative, pestazonatic acid, and four known analogs.[GRAPHICS].

  DOI：

  10.1080/10286020.2017.1395858
• 作为产物：
  描述：

  1,1-二乙氧基环戊烷 在 palladium on activated charcoal lead(IV) acetate 、 高氯酸 、 氢气 、 sodium hydride 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 、 乙腈 、 苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 27.58h， 生成 6-(1,2-二羟基戊基)-4-甲氧基-5,6-二氢吡喃-2-酮
  参考文献：
  名称：

  Kirihata, Mitsunori; Ohta, Kazunari; Ichimoto, Itsuo, Agricultural and Biological Chemistry, 1990, vol. 54, # 9, p. 2401 - 2405

  摘要：

  DOI：

文献信息

• Highly Stereoselective Synthesis and Structural Confirmation of a Fungal Metabolite, LL-P880.BETA..
  作者：Yukio MASAKI、Toshihiro IMAEDA、Makoto KAWAI

  DOI：10.1248/cpb.42.179

  日期：——

  A fungal metabolite, LL-P880β [6S-(1'S, 2'R-dihydroxypentyl)-4-methoxy-5, 6-dihydropyran-2-one] (1), was synthesized unambiguously from diethyl (R, R)-tartrate (3) as a chiral pool via highly stereoselective construction of the C7'-asymmetric carbon of the intermediate 6, 8-dioxabicyclo[3.2.1]octane derivative (8a), and the stereochemistry of the C6-chiral center of the metabolite was chemically confirmed as (S).

  一种真菌代谢物LL-P880β [6S-(1'S, 2'R-二羟基戊基)-4-甲氧基-5, 6-二氢吡喃-2-酮] (1) 是从手性池中的二乙基 (R, R)-酒石酸 (3) 明确合成的，通过高度立体选择性地构建中间体6, 8-二氧杂双环[3.2.1]辛烷衍生物 (8a) 的C7'-不对称碳，并且代谢物的C6-手性中心的立体化学被化学确认为 (S)。
• Cytotoxic and Antifungal Constituents Isolated from the Metabolites of Endophytic Fungus DO14 from Dendrobium officinale
  作者：Ling-Shang Wu、Min Jia、Ling Chen、Bo Zhu、Hong-Xiu Dong、Jin-Ping Si、Wei Peng、Ting Han

  DOI：10.3390/molecules21010014

  日期：——

  Two novel cytotoxic and antifungal constituents, (4S,6S)-6-[(1S,2R)-1, 2-dihydroxybutyl]-4-hydroxy-4-methoxytetrahydro-2H-pyran-2-one (1), (6S,2E)-6-hydroxy-3-methoxy-5-oxodec-2-enoic acid (2), together with three known compounds, LL-P880γ (3), LL-P880α (4), and Ergosta-5,7,22-trien-3b-ol (5) were isolated from the metabolites of endophytic fungi from Dendrobium officinale. The chemical structures were determined based on spectroscopic methods. All the isolated compounds 1–5 were evaluated by cytotoxicity and antifungal effects. Our present results indicated that compounds 1–4 showed notable anti-fungal activities (minimal inhibitory concentration (MIC) ≤ 50 μg/mL) for all the tested pathogens including Candida albicans, Cryptococcus neoformans, Trichophyton rubrum, Aspergillus fumigatus. In addition, compounds 1–4 possessed notable cytotoxcities against human cancer cell lines of HL-60 cells with the IC50 values of below 100 μM. Besides, compounds 1, 2, 4 and 5 showed strong cytotoxities on the LOVO cell line with the IC50 values were lower than 100 μM. In conclusion, our study suggested that endophytic fungi of D. officinale are great potential resources to discover novel agents for preventing or treating pathogens and tumors.

  两种新型细胞毒性和抗真菌成分，(4S,6S)-6-[(1S,2R)-1,2-二羟基丁基]-4-羟基-4-甲氧基四氢-2H-吡喃-2-酮(1)，(6S,2E)-6-羟基-3-甲氧基-5-氧代-2-烯酸(2)、以及三种已知化合物 LL-P880γ (3)、LL-P880α (4) 和 Ergosta-5,7,22-三烯-3b-醇 (5)。其化学结构是根据光谱方法确定的。对所有分离出的化合物 1-5 进行了细胞毒性和抗真菌效果评估。我们目前的研究结果表明，化合物 1-4 对所有测试的病原体（包括白色念珠菌、新型隐球菌、红色毛癣菌和烟曲霉）都具有显著的抗真菌活性（最小抑菌浓度 (MIC) ≤ 50 μg/mL）。此外，化合物 1-4 对人类癌症细胞株 HL-60 细胞具有显著的细胞毒性，其 IC50 值低于 100 μM。此外，化合物 1、2、4 和 5 对 LOVO 细胞系也有很强的细胞毒性，其 IC50 值低于 100 μM。总之，我们的研究表明，D. officinale 的内生真菌是发现预防或治疗病原体和肿瘤的新型药物的巨大潜在资源。
• Divergent synthesis of (6S,1′S,2′R)-hydroxypestalotin via tandem conjugate addition–lactonization sequence
  作者：Venkata Satyanarayana Mallula、Batthula Srinivas、Palakodety Radha Krishna

  DOI：10.1016/j.tetlet.2015.01.069

  日期：2015.2

  The stereoselective synthesis of (65,1'S,2'R)-hydroxypestalotin from trans-hex-2-en-1-ol utilizing asymmetric dihydroxylation and Luche's reduction and tandem conjugative addition-lactonization as the key steps is reported. (C) 2015 Elsevier Ltd. All rights reserved.
• Stereochemistry and biological activities of LL-P880.GAMMA., a pestalotin analogue, produced by Penicillium citreo-viride.
  作者：Yasuo KIMURA、Takashi HAMASAKI、Hiromitsu NAKAJIMA

  DOI：10.1271/bbb1961.50.1649

  日期：——
• KIRIHATA, MITSUNORI;OHTA, KAZUNARI;ICHIMOTO, ITSUO;UEDA, HIROO, AGR. AND BIOL. CHEM., 54,(1990) N, C. 2401-2405
  作者：KIRIHATA, MITSUNORI、OHTA, KAZUNARI、ICHIMOTO, ITSUO、UEDA, HIROO

  DOI：——

  日期：——