fluorene-3-carbaldehyde | 83323-19-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: fluorene-3-carbaldehyde
• 英文别名: 9H-fluorene-3-carbaldehyde
• CAS: 83323-19-7
• 化学式: C₁₄H₁₀O
• 分子量: 194.233
• InChiKey: CYDABVPVQMWWBC-UHFFFAOYSA-N

物化性质

• 沸点：
  362.1±21.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  fluorene-3-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (9H-fluoren-2-yl)methanol
  参考文献：
  名称：

  作为人类17α-羟化酶-17,20-裂解酶（CYP17）抑制剂的亚甲基咪唑取代的联芳基的合成，生物学评估和分子模型研究-第二部分：核心刚性和亚甲基桥上取代基的影响。

  摘要：

  已合成了35种新型取代的咪唑基亚甲基联苯作为CYP17抑制剂，可用于治疗前列腺癌。已经用在大肠杆菌中表达的重组人CYP17测试了它们的活性。测试了有前途的化合物对CYP11B1，CYP11B2和肝CYP酶3A4、1A2、2B6和2D6的选择性。核心刚性化合物（30-35）是最活跃的化合物，比酮康唑更有效，并达到阿比特龙的活性。但是，它们不是非常有选择性。在大鼠中进一步检查了血浆中睾丸激素水平和药代动力学特性的另一种更有效且更具选择性的抑制剂（化合物23，IC（50）= 345 nM）。相较于参考文献Abiraterone，体内有23种活性更高，显示更长的血浆半衰期（10小时）和更高的生物利用度。使用我们的CYP17同源蛋白模型，与选定化合物进行对接研究，以研究抑制剂与活性位点氨基酸残基之间的可能相互作用。

  DOI：

  10.1016/j.bmc.2008.07.011
• 作为产物：
  描述：

  (9H-fluoren-3-yl)methylene diacetate 在 sulfonated rice husk ash 作用下， 以 乙腈 为溶剂， 反应 0.02h， 以91%的产率得到fluorene-3-carbaldehyde
  参考文献：
  名称：

  Sulfonated rice husk ash (RHA-SO3H): A highly powerful and efficient solid acid catalyst for the chemoselective preparation and deprotection of 1,1-diacetates

  摘要：

  Rice husk ash (RHA), as a source of amorphous silica, was treated with chlorosulfonic acid and sulfonated rice husk ash (RHA-SO3H) as a highly powerful solid acid catalyst was obtained and characterized with a variety of techniques including IR, TGA, SEM, XRD, pH analysis, Hammett acidity function and BET method. This solid acid showed excellent catalytic activity for the protection and deprotection of aldehydes with Ac2O at room temperature under solvent free conditions. The procedure gave the products in excellent yields in very short reaction times and good to high yields. Also this catalyst can be reused for several times without loss of its catalytic activity. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.catcom.2013.02.022

文献信息

• Highly Regio- and Enantioselective Reductive Coupling of Alkynes and Aldehydes via Photoredox Cobalt Dual Catalysis
  作者：Yan-Lin Li、Shi-Qi Zhang、Jie Chen、Ji-Bao Xia

  DOI：10.1021/jacs.1c03527

  日期：2021.5.19

  A Co-catalyzed highly regio- and enantioselective reductive coupling of alkynes and aldehydes has been developed under visible light photoredox dual catalysis. A variety of enantioenriched allylic alcohols have been obtained by using unsymmetrical internal alkynes and commercially available catalyst, chiral ligand, and reagents. It is noteworthy that this approach has considerable advantages, such

  在可见光光氧化还原双催化下开发了一种共催化的炔烃和醛的高度区域选择性和对映选择性还原偶联。通过使用不对称内部炔烃和市售催化剂、手性配体和试剂，已经获得了多种对映体富集的烯丙醇。值得注意的是，这种方法具有相当大的优势，例如出色的区域-（> 40 个示例> 95:5）、立体-（高达> 95:5 E / Z）和对映选择性（92-99% ee，> 35个例子）控制，反应条件温和，底物范围广，官能团相容性好，使其对映选择性炔-醛还原偶联反应有了很大的改进。
• Succinimidinium hydrogensulfate ([H-Suc]HSO4) as a new, green and efficient ionic liquid catalyst for the synthesis of tetrahydrobenzimidazo[2,1-b]quinazolin-1(2H)-one, 1-(benzothiazolylamino)phenylmethyl-2-naphthol, 1, 8-dioxo-octahydroxanthene and bis(indolyl)methane derivatives
  作者：Omid Goli-Jolodar、Farhad Shirini

  DOI：10.1007/s13738-016-0822-1

  日期：2016.6

  In this work, succinimidinium hydrogensulfate ([H-Suc]HSO4), a newly reported Brönsted acidic ionic liquid, is used as an efficient and reusable catalyst in the synthesis of tetrahydrobenzimidazo[2,1-b]quinazolin-1(2H)-ones, 1-(benzothiazolylamino)phenylmethyl-2-naphthols, 1,8-dioxo-octahydroxanthenes and bis(indolyl)methanes. All reactions were performed during relatively short reaction times with

  在这项工作中，新报道的布朗斯台德酸性离子液体硫酸氢琥珀酰亚胺（[H-Suc] HSO 4）在合成四氢苯并咪唑并[ 2,1- b ]喹唑啉-1（2 H）中用作有效且可重复使用的催化剂。）-，1-（苯并噻唑基氨基）苯基甲基-2-萘酚，1,8-二氧-八氢氧杂蒽和双（吲哚基）甲烷。所有反应均在相对短的反应时间内进行，并具有优异的收率。通过IR，1 H NMR和13 C NMR光谱对产物的结构进行表征，并通过比较真实样品进行确认。
• Palladium-Catalyzed Reaction of Haloarenes with Diarylethynes: Synthesis, Structural Analysis, and Properties of Methylene-Bridged Arenes
  作者：Che-Wei Lee、En-Chih Liu、Yao-Ting Wu

  DOI：10.1021/acs.joc.5b02111

  日期：2015.11.6

  Fluorenes and methylene-bridged polyarenes were easily and efficiently synthesized from haloarenes (or aryl triflates) and diarylethynes by a one-pot, two-step procedure. This protocol involves the palladium-catalyzed cycloisomerization and a subsequent base-mediated retro-aldol condensation. A major advantage is that the starting materials need not have ortho functional groups to complete the annulation

  芴和亚甲基桥接的聚芳烃可以通过一锅，两步程序从卤代芳烃（或芳基三氟甲磺酸酯）和二芳基乙炔轻松高效地合成。该方案涉及钯催化的环异构化和随后的碱介导的逆醛醇缩合。一个主要的优点是，起始材料不需要具有邻位官能团即可完成环化反应。使用二卤代芳烃，高度π-共轭卤代芳烃或二芳基炔烃扩大了设计产品的骨架。苯并[ a]的形成机理对]芴进行了研究。通过X射线晶体学证实了亚甲基桥联的茚并环戊烯的碗状结构。研究了由此制备的产物的光物理和电化学性质。
• Efficient synthesis of 3-substituted indoles through a domino gold(I) chloride catalyzed cycloisomerization/C3-functionalization of 2-(alkynyl)anilines
  作者：C. Praveen、K. Karthikeyan、P.T. Perumal

  DOI：10.1016/j.tet.2009.09.019

  日期：2009.11

  An efficient synthesis of 3-substituted indoles by a sequential approach involving gold(I) chloride catalyzed cycloisomerization/bis-addition and conjugate addition of 2-(alkynyl)anilines has been accomplished. A variety of 2-(alkynyl)anilines, aldehydes, isatins and nitroolefins undergo this overall process in good to excellent yields. This methodology represents an effective alternative to the classical

  通过包括氯化金（I）催化的环异构化/双加成和2-（炔基）苯胺的共轭加成的顺序方法，已经完成了3-取代的吲哚的有效合成。各种2-（炔基）苯胺，醛，靛红和硝基烯烃以良好或优异的收率经历了整个过程。这种方法代表了吲哚经典C3功能化的有效替代方法。
• Gold(I)-catalyzed sequential cycloisomerization/bis-addition of o-ethynylanilines: an efficient access to bis(indolyl)methanes and di(indolyl)indolin-2-ones
  作者：C. Praveen、Y. Wilson Sagayaraj、P.T. Perumal

  DOI：10.1016/j.tetlet.2008.11.086

  日期：2009.2

  An efficient synthesis of bis(indolyl)methanes and di(indolyl)indolin-2-ones has been developed by a sequential approach involving gold(I)-catalyzed cycloisomerization/bis-addition of o-ethynylanilines with various aldehydes and isatins, respectively. This methodology opens clean and synthetically competitive alternative to the already established procedures of the synthesis of bis(indolyl)methanes

  通过顺序方法已经开发了有效的合成双（吲哚基）甲烷和二（吲哚基）吲哚-2-酮的方法，该方法涉及金（I）催化的邻乙炔基苯胺的环异构化/双加成分别与各种醛和靛红。这种方法为合成双（吲哚基）甲烷和二（吲哚基）吲哚啉-2-酮的既定方法提供了清洁的，具有合成竞争力的替代方法。