(2R)-5-dodecanoyl-2,4-dimethyl-2,3-dihydropyran-6-one | 736177-63-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R)-5-dodecanoyl-2,4-dimethyl-2,3-dihydropyran-6-one
• CAS: 736177-63-2
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: IBSUGPKFCLTAFW-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-5-dodecanoyl-2,4-dimethyl-2,3-dihydropyran-6-one 在 palladium dihydroxide sodium tetrahydroborate 、 氢气 、 对甲苯磺酸 作用下， 以 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 生成 (2R,4S)-4-[(5R)-2,2-dimethyl-4-undecyl-1,3-dioxan-5-yl]pentan-2-ol
  参考文献：
  名称：

  Dihydrodictyopyrones A和C：从网状柄状细胞粘液霉菌中分离出来的dictyopyrone家族的新成员

  摘要：

  我们已经探索了细胞粘液霉菌产生的次生代谢产物的多样性，以评估它们是否是生物潜在物质的宝贵资源。从果蝇双胞胎的子实体的甲醇提取物中，我们获得了新的α-吡喃类化合物，二氢双嘧啶酮A（1）和C（2）。它们的结构，包括绝对构型，是通过光谱方法和不对称总合成来确定的。化合物1和2是dictyopyrone家族的新成员，它们是Dictyostelium细胞粘液霉菌各种物种的特征性次生代谢产物。

  DOI：

  10.1016/j.tetlet.2007.06.040
• 作为产物：
  描述：

  5-(1-hydroxydodecylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 在 sodium ethanolate 、 pyridinium chlorochromate 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 (2R)-5-dodecanoyl-2,4-dimethyl-2,3-dihydropyran-6-one
  参考文献：
  名称：

  Structural requirements of dictyopyrones isolated from Dictyostelium spp. in the regulation of Dictyostelium development and in anti-leukemic activity

  摘要：

  Cellular slime molds are fascinating to the field of developmental biology, and have long been used as excellent model organisms for the study of various aspects of multicellular development. We have recently isolated alpha-pyronoids, named dictyopyrones A-D (1-4), from various species of Dictyostelium cellular slime molds, and it was shown that compound 3 may regulate Dictyostelium development. In this study, we synthesized dictyopyrones A-D (1-4) and their analogues, investigated the physiological role of the molecules in cell growth and morphogenesis in D. discoideum, and further verified their effects on human leukemia K562 cells. Nitrogen-containing compounds 22 and 37 strongly inhibited cell growth in K562 leukemia cells, indicating that these compounds may be utilized as novel lead compounds for anti-leukemic agents. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.001

文献信息

• OSTEOPONTIN PRODUCTION INHIBITOR CONTAINING DICTYOPYRONE DERIVATIVE OR DIHYDRODICTYOPYRONE DERIVATIVE AS ACTIVE INGREDIENT
  申请人：TOHOKU UNIVERSITY

  公开号：US20150366851A1

  公开（公告）日：2015-12-24

  Disclosed herein is an osteopontin production inhibitor capable of preventing a disease resulting from increased production of osteopontin. The osteopontin production inhibitor contains a dictyopyrone derivative or a dihydrodictyopyrone derivative as an active ingredient. The dictyopyrone derivative is preferably a compound represented by Chemical Formula 1 or 2, and the dihydrodictyopyrone derivative is preferably a compound represented by Chemical Formula 3 or 4.

  本公开提供了一种能够防止由于骨桥蛋白过度产生而导致疾病的骨桥蛋白产生抑制剂。该骨桥蛋白产生抑制剂包含二氢骨桥蛋白衍生物或二氢二氢骨桥蛋白衍生物作为活性成分。二氢骨桥蛋白衍生物最好是由化学式1或2表示的化合物，而二氢二氢骨桥蛋白衍生物最好是由化学式3或4表示的化合物。
• US9463188B2
  申请人：——

  公开号：US9463188B2

  公开（公告）日：2016-10-11
• Structural requirements of dictyopyrones isolated from Dictyostelium spp. in the regulation of Dictyostelium development and in anti-leukemic activity
  作者：Haruhisa Kikuchi、Kazunori Sasaki、Jun'ichi Sekiya、Yasuo Maeda、Aiko Amagai、Yuzuru Kubohara、Yoshiteru Oshima

  DOI：10.1016/j.bmc.2004.04.001

  日期：2004.6

  Cellular slime molds are fascinating to the field of developmental biology, and have long been used as excellent model organisms for the study of various aspects of multicellular development. We have recently isolated alpha-pyronoids, named dictyopyrones A-D (1-4), from various species of Dictyostelium cellular slime molds, and it was shown that compound 3 may regulate Dictyostelium development. In this study, we synthesized dictyopyrones A-D (1-4) and their analogues, investigated the physiological role of the molecules in cell growth and morphogenesis in D. discoideum, and further verified their effects on human leukemia K562 cells. Nitrogen-containing compounds 22 and 37 strongly inhibited cell growth in K562 leukemia cells, indicating that these compounds may be utilized as novel lead compounds for anti-leukemic agents. (C) 2004 Elsevier Ltd. All rights reserved.
• Dihydrodictyopyrones A and C: new members of dictyopyrone family isolated from Dictyostelium cellular slime molds
  作者：Haruhisa Kikuchi、Koji Nakamura、Yuzuru Kubohara、Naomi Gokan、Kohei Hosaka、Yasuo Maeda、Yoshiteru Oshima

  DOI：10.1016/j.tetlet.2007.06.040

  日期：2007.8

  secondary metabolites produced by cellular slime molds to evaluate if they are valuable resources for biologically potential substances. From the methanol extract of fruiting bodies of Dicyostelium firmibasis, we obtained new α-pyranoids, dihydrodictyopyrones A (1) and C (2). Their structures including absolute configurations were determined by spectral means and asymmetric total synthesis. Compounds 1 and

  我们已经探索了细胞粘液霉菌产生的次生代谢产物的多样性，以评估它们是否是生物潜在物质的宝贵资源。从果蝇双胞胎的子实体的甲醇提取物中，我们获得了新的α-吡喃类化合物，二氢双嘧啶酮A（1）和C（2）。它们的结构，包括绝对构型，是通过光谱方法和不对称总合成来确定的。化合物1和2是dictyopyrone家族的新成员，它们是Dictyostelium细胞粘液霉菌各种物种的特征性次生代谢产物。