(1R,2R,6S,7S)-tricyclo[5.2.1.02,6]decan-3-one | 129569-57-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2R,6S,7S)-tricyclo[5.2.1.02,6]decan-3-one
• CAS: 129569-57-9
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: ZTSNSBFZDXDTFS-PYHGXSLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,2R,6S,7S)-tricyclo[5.2.1.02,6]decan-3-one 在 氢氧化钾 、 一水合肼 作用下， 以 二乙二醇 为溶剂， 生成 (3aR,4R,7S,7aS)-octahydro-1H-4,7-methanoindene
  参考文献：
  名称：

  Alder,R.W.; Whiting,M.C., Journal of the Chemical Society, 1963, p. 4595 - 4597

  摘要：

  DOI：
• 作为产物：
  描述：

  3-exo-hydroxy-endo-tricyclo<5.2.1.0^2,6>decane 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 (1R,2R,6S,7S)-tricyclo[5.2.1.02,6]decan-3-one
  参考文献：
  名称：

  Pirsch, Chemische Berichte, 1934, vol. 67, p. 1115,1117

  摘要：

  DOI：

文献信息

• A simple strategy for spirocyclopentannulation of cyclic ketones. Formal total synthesis of (±)-acorone
  作者：Adusumili Srikrishna、P Praveen Kumar、Ranganathan Viswajanani

  DOI：10.1016/0040-4039(96)00109-8

  日期：1996.3

  A general and simple methodology for spirocyclopentannulation of cyclic ketones (or 4,4-disubstituted cyclopentenones from acyclic ketones) and its application in the synthesis of the spirodienone via a prochiral precursor constituting a formal total synthesis of (±)-acorone (), are described.

  环酮（或无环酮的4,4-二取代环戊烯酮）螺环戊环化的一般和简单方法及其在构成手性前体的前手性前体合成螺旋二烯酮中的应用构成了（±）-±酮的正式全合成（）。描述。
• Synthesis and evaluation of new chiral diols based on the dicyclopentadiene skeleton
  作者：Giuseppe Borsato、Ottorino De Lucchi、Fabrizio Fabris、Vittorio Lucchini、Pietrogiulio Frascella、Alfonso Zambon

  DOI：10.1016/s0040-4039(03)00664-6

  日期：2003.4

  rac-5 (from reduction of ketone 6, obtained from dicyclopentadiene with a new environment-friendly synthesis) gives (2S)-5, which was further reduced to the endo(2R)-1a alcohol. The endo(2S)-1b alcohol was obtained from camphor with a multistep synthesis. Pinacol couplings of 3a,b, carried out with Mg/Hg or Corey's general procedure respectively, afforded with high diastereoselectivity the C2 symmetry

  脂肪酶PS对rac - 5的拆分（由二环戊二烯的酮6还原，通过新的环境友好合成法制得）得到（2 S）-5，进一步还原为内含（2 R）-1a醇。的内切（2小号- ）1B是从樟脑用多步合成得到的醇。分别用Mg / Hg或Corey's通用方法进行的3a，b的Pinacol偶联可提供非对映选择性高的C 2对称二醇（2 R，2'R）-2a和（2 S，2 'S）-2b具有面向内的OH功能。所述的enantiogenic功率内醇（2 - [R - ）1A和（2小号） - 1B和二醇的（2 - [R，2' - [R ）-图2a和（2小号，2'小号） -图2b是向着的LiAlH测试4还原苯乙酮。在c ^ 2对称性似乎发挥基础性作用。
• An expedient cyclopentenone annulation protocol
  作者：Goverdhan Mehta、Srinivas Rao Karra

  DOI：10.1016/s0040-4039(00)79726-7

  日期：1991.7

  A short and efficient procedure of general applicability for → annulation is described.

  介绍了一种适用于→环行的简短高效的通用方法。
• Alder; Stein, Justus Liebigs Annalen der Chemie, 1933, vol. 504, p. 216,232, 252
  作者：Alder、Stein

  DOI：——

  日期：——
• Stereoselectivity in the Rhodium-Catalysed Reductions of Non-Conjugated Dienes
  作者：Bao Nguyen、John M. Brown

  DOI：10.1002/adsc.200900013

  日期：2009.6

  Abstractmagnified imageThe stereochemical course of rhodium‐catalysed addition of hydrogen and catecholborane to bicyclo[2.2.1]heptadiene, and of hydrogen to a range of cyclic dienes has been analysed. For hydroboration, the overall catalytic reaction possesses exo‐selectivity, but the initial step is endo‐selective. For hydrogenation (deuteration), the first step may occur with either exo‐ or endo‐ selectivity, depending on the structure of the diene. This enables a distinction to be made between pathways involving prior dissociation of the diene, and direct addition to the complexed diene without full dissociation. The relative ease of hydrogenation of the first and second double bonds varies markedly with reactant structure, and also depends on the choice of catalyst ligands. For dicyclopentadiene, hydrogenation of the cyclopentene double bond is accompanied by rapid alkene isomerisation, as revealed by deuterium addition. The asymmetric hydrogenation of acyclic skipped meso‐dienes is reported, demonstrating control of relative rates of the two sequential steps, with ees of up to 53% after the first reduction.