trans-6α-carboethoxybicyclo<4.4.0>decan-3α-ol-9-one | 111219-12-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-6α-carboethoxybicyclo<4.4.0>decan-3α-ol-9-one
• 英文别名: ethyl (2RS,4aRS,8aSR)-2-hydroxy-7-oxodecahydronaphthalene-4a-carboxylate；ethyl c-2-hydroxy-7-oxo-t-8a-decahydronaphthalene-r-4a-carboxylate；trans-6α-carboethoxybicyclo[4.4.0]decan-3α-ol-9-one；ethyl (2R,4aR,8aS)-2-hydroxy-7-oxo-1,2,3,4,5,6,8,8a-octahydronaphthalene-4a-carboxylate
• CAS: 111219-12-6
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: UFNHEXXTWNWSPV-OPQQBVKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  trans-6α-carboethoxybicyclo<4.4.0>decan-3α-ol-9-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以91%的产率得到ethyl c-(2,7)-dihydroxy-t-8a-decahydronaphthalene-r-4a-carboxylate
  参考文献：
  名称：

  Diaxial Diureido Decalins as Compact, Efficient, and Tunable Anion Transporters

  摘要：

  Decalins bearing two axial -NHCONHAr substituents and an ester-linked alkyl side chain have been synthesized and studied as anion receptors and transporters. The design relates to steroid-based "cholapods" but is more compact and less intrinsically lipophilic. Transport rates depend on both NHAr and the alkyl side chain. High activities can be achieved; with optimal substitution, chloride-nitrate exchange across vesicle membranes is measurable at transporter/lipid ratios as low as 1:250000.

  DOI：

  10.1021/ja1076102
• 作为产物：
  描述：

  ethyl 2-hydroxy-7-oxo-2,3,4,4a,5,6-hexahydronaphthalene-r-4a-carboxylate 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醚 为溶剂， 以65%的产率得到trans-6α-carboethoxybicyclo<4.4.0>decan-3α-ol-9-one
  参考文献：
  名称：

  预组织双硫脲作为强大的阴离子载体：单分子大单层囊泡中的氯化物运输

  摘要：

  跨膜阴离子载体（阴离子载体）在生物研究和医学方面具有潜力，前提是可以获得高活性。人们对治疗囊性纤维化 (CF) 尤其感兴趣，这是一种由阴离子转运缺陷引起的遗传疾病。以前的工作发现，以类固醇和反式十氢化萘支架上的轴向尿素为特征的阴离子载体设计可能特别有效。在这里，我们表明用硫脲替代尿素会产生实质性的进一步增强。已制备并测试了六种新的双硫脲在 1-palmitoyl-2-oleoylphosphatidylcholine/胆固醇大单层囊泡 (LUV) 中的 Cl(-)/NO3(-) 交换。双硫脲通常比相应的脲有效 10 倍以上，并且具有足够的活性，可以很容易地检测到在 LUV 中单独作用的分子的传输。十氢化萘 9 显示出最高的活性，它具有 N-(3,5-双(三氟甲基)苯基)硫脲基和辛酯取代基。200 nm 囊泡中的单个转运蛋白 9 分子促进 Cl(-)/NO3(-) 交换，半衰期为 45 秒，绝对速率为每秒

  DOI：

  10.1021/ja507551z

文献信息

• Toosendanin: Synthesis of the AB-ring and investigations of its anti-botulinum properties (Part II)
  作者：Yuya Nakai、Sabine Pellett、William H. Tepp、Eric A. Johnson、Kim D. Janda

  DOI：10.1016/j.bmc.2009.12.030

  日期：2010.2

  and a characteristic flaccid paralysis of humans. The natural product toosendanin, a limonoid, is a traditional Chinese medicine that has reported anti-botulinum properties in animal models. Toosendanin effectively inhibits the biological activity of BoNT/A in neuronal cells at concentrations of 200 nM, and partial inhibition can be observed with concentrations as low as 8 nM. Mechanistically, toosendanin’s

  肉毒杆菌神经毒素 (BoNT) 是导致肉毒杆菌中毒的病原体，肉毒杆菌中毒是一种以周围神经肌肉阻滞为特征的疾病，是人类特有的弛缓性麻痹。天然产物川楝素是一种传统中药，已在动物模型中报告了抗肉毒杆菌的特性。川楝素在 200 nM 的浓度下可有效抑制神经元细胞中 BoNT/A 的生物活性，低至 8 nM 的浓度即可观察到部分抑制。从机制上讲，川楝素的抑制作用是由于阻止了 BoNT LC 通过 HC 通道的转导。关于川楝素分子结构及其抗肉毒杆菌特性的有趣问题使我们的注意力集中在川楝素不寻常的 AB 环的合成上，含有独特的桥接半缩醛。在目前的工作中，一种允许访问川楝素 AB 片段的合成策略是从反式萘烷系统。此外，在大鼠脊髓细胞试验中检查了该片段对 BoNT/A 中毒的调节。
• Model Studies Towards Azadirachtin: Part 1. Construction of the Crowded C8bC14 Bond by Radical Chemistry We thank Drs. D. H. Huang and G. Siuzdak for NMR spectroscopic and mass spectrometric assistance, respectively. This work was financially supported by the National Institutes of Health (USA), the Skaggs Institute for Chemical Biology, postdoctoral fellowships from Bayer AG (to M.F.) and the G. E. Hewitt Foundation (to K.W.H.), a predoctoral fellowship from the Division of Organic Chemistry of the American Chemical Society sponsored by Novartis (to A.J.R.), and grants from Abbott Laboratories, ArrayBiopharma, Bayer, Boehringer Ingelheim, DuPont, Glaxo, Hoffmann-LaRoche, Merck, Novartis, Pfizer, and Schering Plough.
  作者：K. C. Nicolaou、Markus Follmann、A. J. Roecker、Kevin W. Hunt

  DOI：10.1002/1521-3773(20020617)41:12<2103::aid-anie2103>3.0.co;2-s

  日期：2002.6.17
• Ring differentiation of the trans-decahydronaphthalene system via chemo-enzymatic dissymmetrization of its σ-symmetric glycol: Synthesis of a highly functionalized chiral building block for the terpene synthesis
  作者：Naoki Toyooka、Akira Nishino、Takefumi Momose

  DOI：10.1016/0040-4039(93)88079-x

  日期：1993.7

  The asymmetric ring differentiation by lipase-catalyzed transesterification of a meso decahydronaphthalenediol (1) was accomplished in extremely high optical and chemical yield. The absolute stereochemistry of the corresponding mono-acetate(-)-2 was determined by its conversion into a decalone [(-)-31 and to an octalone [(+)-4], which were key intermediates for the synthesis of (-)-polygodial, (-)-warburganal, and (-)-drimenin.
• Model Studies Towards Azadirachtin: Part 2. Construction of the Crowded C8bC14 Bond by Transition Metal Chemistry We thank Drs. D. H. Huang and G. Siuzdak for NMR spectroscopic and mass spectrometric assistance, respectively. This work was financially supported by the National Institutes of Health (USA), the Skaggs Institute for Chemical Biology, a predoctoral fellowship from the Division of Organic Chemistry of the American Chemical Society sponsored by Novartis (to A.J.R.), postdoctoral fellowships from Bayer AG (to M.F.), and Association pour la Recherche sur le Cancer (to R.B.), and grants from Abbott Laboratories, ArrayBiopharma, Bayer, Boehringer Ingelheim, DuPont, Glaxo, Hoffmann-LaRoche, Merck, Novartis, Pfizer, and Schering Plough.
  作者：K. C. Nicolaou、A. J. Roecker、Markus Follmann、Rachid Baati

  DOI：10.1002/1521-3773(20020617)41:12<2107::aid-anie2107>3.0.co;2-4

  日期：2002.6.17
• Jones, J. Bryan; Dodds, David R., Canadian Journal of Chemistry, 1987, vol. 65, p. 2397 - 2404
  作者：Jones, J. Bryan、Dodds, David R.

  DOI：——

  日期：——