ethyl 2-hydroxy-7-oxo-2,3,4,4a,5,6-hexahydronaphthalene-r-4a-carboxylate | 5009-24-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-hydroxy-7-oxo-2,3,4,4a,5,6-hexahydronaphthalene-r-4a-carboxylate
• 英文别名: 6-carbethoxy-bicyclo<4.4.0>deca-1,9-diene-9-ol-3-one；4a-Carboethoxy-7-hydroxy-4,4a,5,6-tetrahydro-2(3H)-naphthalenone；ethyl 2-hydroxy-7-oxo-3,4,5,6-tetrahydronaphthalene-4a-carboxylate
• CAS: 5009-24-5
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: OBOXQMDDTDEIBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-hydroxy-7-oxo-2,3,4,4a,5,6-hexahydronaphthalene-r-4a-carboxylate 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 17.0h， 生成 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：

  2-甲基-4-羰基-2-环己烯-1-羧酸乙酯 、 3-氯丙酸乙酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以37%的产率得到ethyl 2-hydroxy-7-oxo-2,3,4,4a,5,6-hexahydronaphthalene-r-4a-carboxylate
  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

• Ultraviolet radiation absorbing naphthalenylidene compositions
  申请人：ICI Americas Inc.

  公开号：US04889947A1

  公开（公告）日：1989-12-26

  Sunscreen compositions are described which contain certain substituted naphthalenylidenes which act as UV filters when incorporated in a carrier in amounts ranging from 0.1-50% by weight.

  描述了一种含有某些取代萘亚亚甲基化合物的防晒配方，当以0.1-50%的重量比例加入载体中时，这些化合物可以作为紫外线过滤剂。
• 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.
• Enantiodivergent synthesis of a decalin type of chiral building blocks and their application to terpenoid synthesis
  作者：Naoki Toyooka、Akira Nishino、Takefumi Momose

  DOI：10.1016/s0040-4020(97)00315-3

  日期：1997.5

  An enantiomeric pair of a decalin type of chiral building blocks bearing an oxygenated angular substituent has been synthesized by the lipase-mediated ring differentiation of a meso decahydronaphthalene glycol system Its synthetic utility has been demonstrated by the formal synthesis of (-)-polygodial, (-)-warburganal, (-)-drimenin, and (-)-elemol. (C) 1997 Elsevier Science Ltd.
• 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：——
• JONES, J. BRYAN;DODDS, DAVID R., CAN. J. CHEM., 65,(1987) N 10, 2397-2404
  作者：JONES, J. BRYAN、DODDS, DAVID R.

  DOI：——

  日期：——