螺[环戊烷-1,9'-芴] | 14966-37-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 螺[环戊烷-1,9'-芴]
• 英文名称: spiro[cyclopentane-1,9'-fluorene]
• CAS: 14966-37-1
• 化学式: C₁₇H₁₆
• 分子量: 220.314
• InChiKey: AFYJRAFRYWVOOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2',7'-dibromospiro[cyclopentane-1,9'-fluorene]	441771-49-9	C17H14Br2	378.106
  2'-溴螺[环戊烷-1,9'-芴]	2'-bromospiro[cyclopentane-1,9'-fluorene]	797056-47-4	C17H15Br	299.21
  ——	2',7'-bis(4-cyanophenyl)spiro[cyclopentane-1,9'-fluorene]	——	C31H22N2	422.529
  ——	2',7'-di(2-thienyl)spiro[cyclopentane-1,9'-fluorene]	——	C25H20S2	384.566
  ——	2',7'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopentane-1,9'-fluorene]	441771-50-2	C29H38B2O4	472.24

反应信息

• 作为反应物：
  描述：

  螺[环戊烷-1,9'-芴] 在 溴 、 三氯化铁 作用下， 以 氯仿 为溶剂， 反应 4.3h， 以85%的产率得到2',7'-dibromospiro[cyclopentane-1,9'-fluorene]
  参考文献：
  名称：

  Synthesis and crystal structure and optical properties of fluorenic-core oligomers

  摘要：

  氟烯核寡聚物通过有机金属方法合成，显示出有趣的光致发光特性。对一个氟烯衍生物及三种同系寡聚物的晶体和分子结构进行了研究。二溴氟烯的螺旋衍生物显示出氢原子与溴原子之间非常强的相互作用。带有螺旋取代基的噻吩末端寡聚物采用特定的鱼骨排列，仅有末端噻吩残基重叠，且构象无序。全苯衍生物的晶体由靠面排列的离散分子堆积而成。带有线性烷基链的氟烯核心在9位上的分子，末端为噻吩环，表现出多晶型，其晶体结构为四方形，非常奇特，因为其松散的堆积允许相邻的噻吩环之间有良好的分离。 研究了这一系列的吸收和发射特性，并对单层器件的电致发光进行了表征。这些分子的光致发光特性强烈依赖于其结构组织，发射从无定相到晶体结构再到聚集形态表现出红移。 对这些寡聚物和寡噻吩烯的堆积进行比较，充分说明了所报道分子的光学特性。

  DOI：

  10.1039/b109089p
• 作为产物：
  描述：

  芴 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.5h， 生成 螺[环戊烷-1,9'-芴]
  参考文献：
  名称：

  Orbital distortion arising from remote substituents. Nitration, reduction, and epoxidation of fluorenes bearing a carbonyl or an olefin group in spiro geometry

  摘要：

  Nitration of spiro[cyclopentane-1,9'-fluoren]-2-one with acetyl nitrate predominantly gave the 4-nitro derivative. In the reduction of substituted spiro[cyclopentane-1,9-fluoren]-2-ones, the anti alcohols were favored in all cases. In the epoxidation of substituted spiro[cyclopent-2-ene-1,9'-fluorenes], the syn epoxides were favored. These distributions of the products can be interpreted in terms of orbital perturbations arising from interactions of the pi orbitals of the aromatic and the carbonyl moieties or of the pi orbitals of the aromatic and the olefin moieties, i.e., orbital mixing perturbation of the aromatic pi orbitals through the pi orbital of the bisected carbonyl (or olefin) group and the reciprocal perturbation of the pi orbital of the carbonyl (or olefin) group arising from the orthogonal pi aromatic orbitals.

  DOI：

  10.1021/ja00049a012

文献信息

• COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
  申请人：Samsung Display Co., Ltd.

  公开号：US20210053920A1

  公开（公告）日：2021-02-25

  An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes the compound of Formula 1: When the compound of Formula 1 is used in an organic light-emitting device, the organic light-emitting device may have high-efficiency characteristics as compared to a case where a compound of the related art is used, resulting particularly in excellent lifespan improvement effects, and accordingly, significantly improved lifespan.

  一种有机发光器件包括：第一电极；面向第一电极的第二电极；以及位于第一电极和第二电极之间的有机层，包括一个发射层，其中有机层包括化合物Formula 1：当化合物Formula 1在有机发光器件中使用时，与使用相关技术的化合物相比，有机发光器件可能具有高效特性，特别是在寿命改善效果方面表现出色，因此，寿命得到显著提高。
• The one-electron oxidation of biphenyl-2-ylethylenes. Subsequent chemical reactivity controlled by electron return or proton transfer
  作者：Ren� Lapouyade、Patrice Villeneuve、Aziz Nourmamode、Jean-Pierre Morand

  DOI：10.1039/c39870000776

  日期：——

  Biphenyl-2-ylethylenes react with (4-BrC6H4)3N˙+SbCl6– to give the radical cation of the electrocyclization product which initiates a protic catalysis to the related fluorenes or, in presence of 2,6-di-t-butylpyridine or water, lead stoicheiometrically to phenanthrenes; with photochemical oxidants only phenanthrenes or 9,10-dihydrophenanthrenes are obtained, with an efficiency related to the polarity

  联苯-2- ylethylenes与反应（4- BRC 6 ħ 4）3 Ñ +的SbCl 6 - ，得到发起质子催化现有芴，或在2,6-二存在下electrocyclization产物的自由基阳离子-叔丁基吡啶或水，从化学计量学上导致菲；用光化学氧化剂只能得到菲或9，10-二氢菲，其效率与溶剂的极性以及三重态供体和自由基离子对的相对能量有关。
• Orbital distortion arising from remote substituents nitration and reduction of spiro(cyclopenta-1,9'-fluorene)-2-ones.
  作者：Tomohiko OHWADA、Koichi SHUDO

  DOI：10.1248/cpb.39.2176

  日期：——

  Nitration of spiro[cyclopenta-1, 9'-fluorene]-2-one with acetyl nitrate predominantly gave the 4-nitro derivative. In the reduction of substituted spiro[cyclopenta-1, 9'-fluorene]-2-ones, the anti-alcohols were favored in all cases. Both anomalous distributions of the products can be interpreted in terms of interactions of the π orbitals of the aromatic and the carbonyl moieties. This example of stereoelectronic effects demonstrates intrinsic reciprocal distortion between sterically unbiased π frameworks of the molecule.

  螺[环戊-1, 9'-芴]-2-酮与乙酰基硝酸盐的硝化主要产生4-硝基衍生物。在取代螺[环戊-1, 9'-芴]-2-酮的还原中，在所有情况下，抗醇剂都受到青睐。产物的两种反常分布都可以用芳香族和羰基部分的π轨道的相互作用来解释。这个立体电子效应的例子证明了分子空间无偏 π 框架之间固有的相互畸变。
• Fluorene‐Chloroquine Hybrids: Synthesis, <i>in vitro</i> Antiplasmodial Activity, and Inhibition of Heme Detoxification Machinery of <i>Plasmodium falciparum</i>
  作者：Parth、Navpreet Kaur、Constance Korkor、Shaikh M. Mobin、Kelly Chibale、Kamaljit Singh

  DOI：10.1002/cmdc.202200414

  日期：2022.10.6

  Fluorene-chloroquine hybrids represent a new class of highly active antiplasmodial agents. The most active compound shows high in vitro antiplasmodial activity (IC50=139 nM) against a chloroquine-sensitive NF54 strain of the human malaria parasite Plasmodium falciparum. The hybrid binds to hemin and inhibits β-hematin formation and impacts the detoxification machinery in P. falciparum.

  疟疾排毒：芴-氯喹杂化物代表了一类新型的高效抗疟原虫药物。活性最强的化合物对人类疟疾寄生虫恶性疟原虫的氯喹敏感 NF54 菌株显示出高体外抗疟原虫活性 (IC 50 =139 nM) 。该杂合体与血红素结合并抑制 β-血红素的形成，并影响恶性疟原虫的解毒机制。
• EP1852129
  申请人：——

  公开号：——

  公开（公告）日：——