2-bromo-7-methoxy-9H-fluoren-9-one | 23683-72-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-bromo-7-methoxy-9H-fluoren-9-one
• 英文别名: 2-Methoxy-7-bromfluorenon；2-Bromo-7-methoxyfluoren-9-one
• CAS: 23683-72-9
• 化学式: C₁₄H₉BrO₂
• 分子量: 289.128
• InChiKey: TYUPSWQHAAYLNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-7-methoxy-9H-fluoren-9-one 在 4-二甲氨基吡啶 、 水 、 氢溴酸 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 136.0h， 生成 7-bromo-9-oxo-9H-fluoren-2-yl 3,4,5-tris(dodecyloxy)benzoate
  参考文献：
  名称：

  Enantiomers Self-Sort into Separate Counter-Twisted Ribbons of the Fddd Liquid Crystal─Antiferrochirality and Parachirality

  摘要：

  DOI：

  10.1021/jacs.3c06164
• 作为产物：
  描述：

  在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 以96 %的产率得到2-bromo-7-methoxy-9H-fluoren-9-one
  参考文献：
  名称：

  Enantiomers Self-Sort into Separate Counter-Twisted Ribbons of the Fddd Liquid Crystal─Antiferrochirality and Parachirality

  摘要：

  DOI：

  10.1021/jacs.3c06164

文献信息

• Synthesis of Fluorenones from Benzaldehydes and Aryl Iodides: Dual C–H Functionalizations Using a Transient Directing Group
  作者：Xiao-Yang Chen、Seyma Ozturk、Erik J. Sorensen

  DOI：10.1021/acs.orglett.7b00161

  日期：2017.3.3

  The first synthesis of substituted fluorenones directly from benzaldehydes and aryl iodides via a Pd(II)-catalyzed C(sp2)-H functionalization cascade is reported. Featuring anthranilic acid as an inexpensive transient directing group, the process is compatible with a variety of benzaldehydes and aryl iodides. A three-step synthesis of the antiviral drug Tilorone was completed in an excellent overall

  报道了通过Pd（II）催化的C（sp2）-H官能化级联直接从苯甲醛和碘代芳烃直接合成取代的芴酮的方法。该工艺以邻氨基苯甲酸为廉价的瞬态导向基团，可与多种苯甲醛和碘代芳基相容。以优异的总收率（40％）完成了抗病毒药物替洛龙的三步合成，证明了该方法的实用性。
• Dual-role catalysis of iridium in photo-irradiation synthesis of 9-fluorenone through intramolecular cyclization <i>via</i> hydrogen evolution
  作者：Xi Hong、Yi-Wen Zhang、Bing Zhan、Xue-Juan Chen、De-Jun Hu、Zhi-Ming Li、Xiu-Feng Hou

  DOI：10.1039/d3cy01353g

  日期：——

  the dehydrogenation. The catalyst [Ir(Fmpbo)2dtbppy]PF6 played a dual role as both the photoredox catalyst to initiate the benzoyl radical reaction and the TM catalyst to finish the aromatization and the hydrogen evolution. The photoredox/TM dual catalytic role of the Ir catalyst was proposed firstly. The reactions provide good to excellent yields of the products under mild and economic conditions.

  以2-芳基苯并[ d ]恶唑基铱配合物为双用途催化剂，由[1,1'-联苯]-2-羧酸光氧化还原催化合成9-芴酮。首次发现了伴随 9-芴酮形成的不寻常的析氢反应。形成的氢的量与9-芴酮成正比，这使得反应原子经济。结合DFT计算，提出了铱催化剂的配体解离过程来解释脱氢反应。催化剂[Ir(Fmpbo) 2 dtbppy]PF 6发挥双重作用，既作为引发苯甲酰自由基反应的光氧化还原催化剂，又作为完成芳构化和析氢的TM催化剂。首次提出Ir催化剂的光氧化还原/TM双重催化作用。该反应在温和且经济的条件下提供了良好至优异的产物收率。
• Supertwisted Chiral Gyroid Mesophase in Chiral Rod‐Like Compounds
  作者：Yan Wang、Shu‐Gui Yang、Ya‐Xin Li、Yu Cao、Feng Liu、Xiang‐Bing Zeng、Liliana Cseh、Goran Ungar

  DOI：10.1002/anie.202403156

  日期：2024.6.3

  Among the intriguing bicontinuous self‐assembled structures, the gyroid cubic is the most ubiquitous. It is found in block and star polymers, surfactants with or without solvent, in thermotropic liquid crystals with end‐ or side‐chains, and in biosystems providing structural color and modelling cell mitosis. It contains two interpenetrating networks of opposite chirality and is thus achiral if, as usual, the content of the two nets is the same. But we now find that this is not the case for strongly chiral compounds. While achiral molecules follow the opposite twists of nets 1 and 2, molecules with a chiral center in their rod‐like core fail to follow the 70° twist between junctions in net 2 and instead wind against it by ‐110° to still match the junction orientation. The metastable chiral gyroid is a high‐entropy high‐heat‐capacity mesophase. The homochirality of its nets makes the CD signal of the thienofluorenone compounds close to that in the stable I23 phase with 3 isochiral nets.