(1R,2R,3S,7S,8S,10S)-3,10-dihydroxy-3,5,8,10-tetramethyltricyclo[6.2.2.02,7]dodeca-5,11-diene-4,9-dione | 146076-45-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,3S,7S,8S,10S)-3,10-dihydroxy-3,5,8,10-tetramethyltricyclo[6.2.2.02,7]dodeca-5,11-diene-4,9-dione
• CAS: 146076-45-1
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: SYNMHQWAAMUPDP-XVMRNDPNSA-N

物化性质

• 熔点：
  180 °C
• 沸点：
  460.6±45.0 °C(predicted)
• 密度：
  1.267±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,6-二甲基苯酚 生成 (1R,2R,3S,7S,8S,10S)-3,10-dihydroxy-3,5,8,10-tetramethyltricyclo[6.2.2.02,7]dodeca-5,11-diene-4,9-dione
  参考文献：
  名称：

  KNEIFEL, HELMUT;POSZICH-BUSCHER, CARMENG;RITTICH, SUSANNE;BREITMAIER, EBE+, ANGEW. CHEM., 103,(1991) N, C. 189-190

  摘要：

  DOI：

文献信息

• Asymmetric Hydroxylative Phenol Dearomatization Promoted by Chiral Binaphthylic and Biphenylic Iodanes
  作者：Cyril Bosset、Romain Coffinier、Philippe A. Peixoto、Mourad El Assal、Karinne Miqueu、Jean-Marc Sotiropoulos、Laurent Pouységu、Stéphane Quideau

  DOI：10.1002/anie.201403571

  日期：2014.9.8

  The long‐standing quest for chiral hypervalent organoiodine compounds (i.e., iodanes) as metal‐free reagents for asymmetric synthesis continues. Although remarkable progress has recently been made in organoiodine‐catalyzed reactions using a terminal oxidant in stoichiometric amounts, there is still a significant need for “flaskable” chiral iodane reagents. Herein, we describe the synthesis of new iodobinaphthyls

  长期以来，对手性高价有机碘化合物（即碘）作为不对称合成的无金属试剂的追求仍在继续。尽管最近使用化学计量的末端氧化剂在有机碘催化的反应中取得了显着进展，但是仍然非常需要“易燃”的手性碘试剂。在本文中，我们描述的新iodobinaphthyls和iodobiphenyls，他们成功的和有选择性的DMDO介导的氧化的合成成任一λ 3 -或λ 5个-iodanes，和它们的能力的评估，以促进非对称hydroxylative苯酚脱芳构化（HPD）的反应。最值得注意的是，一个C 2 -symmetrical biphenylicλ 5碘烷促进了HPD诱导的单萜百里酚转化为相应的基于邻喹啉的[4 + 2]环二聚体（即bis（thymol）），对映体过量高达94％。
• Facile synthesis of amino acid-derived novel chiral hypervalent iodine(V) reagents and their applications
  作者：Yasushi Yoshida、Akina Magara、Takashi Mino、Masami Sakamoto

  DOI：10.1016/j.tetlet.2016.10.016

  日期：2016.11

  Amino acid-derived novel chiral hypervalent iodine(V) reagents were synthesized from the corresponding chiral iodoarenes through DMDO oxidations. Their oxidation states were determined by the 13C NMR chemical shifts of the ipso-carbon of the iodine atom, HRMS analysis, and elemental analyses. They were applied to the enantioselective hydroxylative dearomatization/[4+2]-dimerization cascade reactions

  从相应的手性碘芳烃通过DMDO氧化合成了氨基酸衍生的新型手性高价碘试剂。它们的氧化态由碘原子的ipso-碳的13 C NMR化学位移，HRMS分析和元素分析确定。将它们用于苯酚衍生物的对映选择性羟基化脱芳香化/ [4 + 2]-二聚级联反应，得到所需产物，其ee最高为58％。
• Organocatalytic Enantioselective Synthesis of Bicyclo[2.2.2]octenones via Oxaziridinium Catalysed <i>ortho</i> ‐Hydroxylative Phenol Dearomatization**
  作者：Tom D. D'Arcy、Mark R. J. Elsegood、Benjamin R. Buckley

  DOI：10.1002/anie.202205278

  日期：2022.7.25

  An enantioselective, oxaziridinium-catalysed ortho-hydroxylative dearomatization-[4+2] dimerization reaction of phenols is described. This classically challenging transformation was successfully employed in the synthesis of bis(monoterpenoid) (+)-biscarvacrol and bacterial metabolite (−)-bis(2,6-xylenol), with high enantioselectivity. Our simple, organocatalytic system tolerates multiple phenol substitution

  描述了苯酚的对映选择性、oxaziridinium 催化的邻羟基脱芳构化-[4+2] 二聚反应。这种具有经典挑战性的转化成功地用于合成具有高对映选择性的双（单萜）（+）-双香芹酚和细菌代谢物（-）-双（2,6-二甲苯酚）。我们简单的有机催化系统可耐受多种苯酚取代模式和邻位取代基。
• Asymmetric Oxidation of <i>o-</i>Alkylphenols with Chiral 2-(<i>o-</i>Iodoxyphenyl)-oxazolines
  作者：Jagadish K. Boppisetti、Vladimir B. Birman

  DOI：10.1021/ol8029092

  日期：2009.3.19

  A new class of chiral iodine(V) derivatives has been prepared. These compounds have been found to transform ortho-alkylphenols into ortho-quinol Diels-Alder dimers with significant levels of asymmetric induction.