ethyl c-(2,7)-dihydroxy-t-8a-decahydronaphthalene-r-4a-carboxylate | 152089-86-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl c-(2,7)-dihydroxy-t-8a-decahydronaphthalene-r-4a-carboxylate
• 英文别名: ethyl 2,7-dihydroxydecahydronaphthalene-4a-carboxylate
• CAS: 152089-86-6
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: JLRSUMKMVOQGLK-UPFUWZEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 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：
  0.92
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl c-(2,7)-dihydroxy-t-8a-decahydronaphthalene-r-4a-carboxylate 在 sodium azide 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.42h， 生成 ethyl t-(2,7)-diazido-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 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

文献信息

• Total Synthesis and Biological Evaluation of 19-Hydroxysarmentogenin-3<i>-O</i>-α-<scp>l</scp>-rhamnoside, Trewianin, and Their Aglycons
  作者：Daisuke Urabe、Yuki Nakagawa、Ken Mukai、Kei-ichiro Fukushima、Naoto Aoki、Hiroaki Itoh、Masanori Nagatomo、Masayuki Inoue

  DOI：10.1021/acs.joc.8b02219

  日期：2018.11.16

  Cardenolides comprise an important family of natural steroids with a wide spectrum of biological activities. Although 19-hydroxysarmentogenin-3-O-α-l-rhamnoside (1a) and trewianin (1b) were structurally determined to have cardenolide structures, their biological activities have not been evaluated. The 6/6/6/5-membered ABCD-ring systems of both 1a and 1b are decorated by a β-oriented C17-butenolide

  胡萝卜素包括重要的天然类固醇家族，具有广泛的生物活性。尽管19-hydroxysarmentogenin -3- ö -α-升-rhamnoside（1A）和trewianin（1B）的结构确定为具有cardenolide的结构，它们的生物活性没有被评估。1a和1b的6/6/6/5元ABCD环系统均由一个β定向的C17-丁烯内酯，三个C11、14、19-羟基和C3-O- 1-鼠李糖苷部分修饰。另一方面，1a和1b在C5位是差向异构体。1a和1b的结构通过应用收敛和统一的策略从四个简单的片段中组合而成。的AB环10A / b和d-环8 / 9被暂时束缚在缩醛部分，以及随后的立体选择性6-外型自由基反应连接的两个片段。接下来，醛醇缩合反应使得能够同时引入5aa和54的C环的三个新的立体中心。C17-丁烯内酯的附着导致糖苷配基2a和2b。然后将1-鼠李糖安装到2a和2b中以产生目标1a和1b分别
• 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.