1-ethyl-9H-fluoren-9-one | 166985-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 1-ethyl-9H-fluoren-9-one
• 英文别名: 1-Ethylfluoren-9-one
• CAS: 166985-46-2
• 化学式: C₁₅H₁₂O
• 分子量: 208.26
• InChiKey: PWPUICVJFSMOMF-UHFFFAOYSA-N

物化性质

• 熔点：
  93.5-94.5 °C
• 沸点：
  370.2±12.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  1-ethyl-9H-fluoren-9-one 在 manganese(IV) oxide 、 氢氧化钾 、 盐酸肼 、 silica gel 、 一水合肼 、 sodium sulfate 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 1-ethyl-9-diazofluorene
  参考文献：
  名称：

  Chemistry of 1-Alkylfluorenylidenes. Steric Effects on Arylcarbene Reactivities

  摘要：

  9-Diazofluorenes (RDAF, 1) having a series of alkyl (R) groups from Me to tBu at the 1-position were prepared and decomposed to generate the corresponding fluorenylidenes (RFL, 2) under various conditions in order to examine steric effects on the reactivities of carbenes. Thus, in cyclohexane, singlet fluorenylidenes ((1)RFLs) gave 9-cyclohexylfluorenes while triplet states ((3)RFLs) underwent H abstraction to give 9-fluorenyl (RFLH(.)), which eventually led to fluorene (4, RFLH(2)) and 9,9'bifluorenyl (5), and the ratio of the triplet products to the singlet was increased as more bulky R groups were introduced at the 1-position. These results are interpreted in terms of the steric effects on singlet reactivity, which requires formation of two bonds simultaneously. Generation of tBuFL resulted in the almost exclusive formation of intramolecular reaction products which involved not only insertion of carbene into the delta-C-H bonds of the tert-butyl group but also insertion of the 1,5-biradical, followed by neophyl-type rearrangement. The results are understood as indicating that abstraction of the delta-H by (3)tBuFL gains over the concerted intramolecular C-H insertion in (1)tBuFL. Generation of 1-RFL (R = Et, iPr, tBu) in the gas phase at high temperature gave intramolecular reaction products both in singlet and in triplet states, but the ratio of the singlet to the triplet product increased in going from Et to iPr to tBu presumably due to the increased opportunities of (1)FL to be trapped by delta-C-H bonds. Spectroscopic studies using matrix isolation techniques as well as laser flash photolysis were also carried out to gain information on the intermediates.

  DOI：

  10.1021/ja00121a007
• 作为产物：
  描述：

  二氢-3-(异十二碳烯基)呋喃-2,5-二酮 在 甲烷磺酸 、 仲丁基锂 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 3.0h， 生成 1-ethyl-9H-fluoren-9-one
  参考文献：
  名称：

  未受保护的联苯-2-、-3- 和 -4- 羧酸的方便和区域选择性金属化

  摘要：

  未保护的联苯-2-羧酸可以在与羧酸盐相邻的位置用仲丁基锂完全金属化，然后可以进行位点选择性亲电取代。在 20–60 °C 的 THF 或苯中，正丁基锂和叔丁醇钾（LICKOR，3.5 当量）的超碱性混合物会攻击远程 C2' 位。所得二价阴离子环化得到芴酮骨架。还描述了联苯-3-和-4-羧酸的金属化反应。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200500469

文献信息

• Combined directed ortho metalation—intramolecular Friedel–Crafts connections. Regiospecific route to 1-substituted fluoren-9-ones
  作者：David Tilly、Subhendu S Samanta、Ferenc Faigl、Jacques Mortier

  DOI：10.1016/s0040-4039(02)01976-7

  日期：2002.11

  ortho-Substituted-2-biphenyl carboxylic acids of the type 3a–j were prepared by the tandem metalation sequence from 2-biphenyl carboxylic acid 1 with sec-butyllithium in THF at −78°C followed by quenching with electrophiles. The carboxylic acids 3a–f were converted into 1-substituted fluorenones 4a–f upon treatment with methanesulfonic acid.

  通过串联金属化反应，从2-联苯基羧酸1与仲丁基锂在THF中在-78°C下串联反应，制得3a – j型邻位取代的2-联苯基羧酸，然后用亲电试剂淬灭。用甲磺酸处理后，羧酸3a – f被转化为1-取代的芴酮4a – f。
• [EN] FUCOSIDASE INHIBITORS<br/>[FR] INHIBITEURS DE FUCOSIDASE
  申请人：RAPTOR PHARMACEUTICALS INC

  公开号：WO2017019925A1

  公开（公告）日：2017-02-02

  The present disclosure relates, in general, to compounds useful as inhibitors of fucosidase enzymes, and to methods and compositions for the treatment of tumors or cancers, such as liver disorders and liver tumors (e.g., hepatocellular carcinoma), with a compound as disclosed herein.

  本公开涉及一般而言，用作葡萄糖酶酶抑制剂的化合物，以及使用本公开披露的化合物进行肿瘤或癌症治疗的方法和组合物，例如肝功能障碍和肝肿瘤（例如肝细胞癌）。
• CATHEPSIN S INHIBITORS
  申请人：Lin Chun-Cheng

  公开号：US20110166141A1

  公开（公告）日：2011-07-07

  Cathepsin S inhibitors having formula (I), (II), (III) or (IV) as shown in the specification. These inhibitors can be used to treat cancer and autoimmune/inflammatory diseases.

  具有(I)、(II)、(III)或(IV)公式的卡特普西林S抑制剂，如规范所示。这些抑制剂可用于治疗癌症和自身免疫/炎症性疾病。
• Norbornene Derivatives-Controlled Palladium-Catalyzed Divergent Synthesis of Dibenzo[<i>a</i>,<i>c</i>]cycloheptenones and Fluorenones from Aryl Iodides and α-Oxocarboxylic Acids
  作者：Liwei Zhou、Pengyang Jing、Zhiwei Li、Rui Liu、Jiannan Chen、Guobo Deng、Yun Liang、Yuan Yang

  DOI：10.1021/acs.orglett.3c04065

  日期：2024.1.26

  A palladium-catalyzed divergent cascade decarboxylative annulation of aryl iodides and α-oxocarboxylic acids using norbornene (NBE) derivatives as a controlled switch is reported. When NBE is used as a mediator, fluorenones are synthesized with moderate to excellent yields via a Catellani reaction that involves sequential ortho-C–H arylation and ipso-decarboxylative acylation of aryl iodides. Employing

  据报道，使用降冰片烯（NBE）衍生物作为受控开关，钯催化芳基碘化物和α-氧代羧酸的发散级联脱羧成环。当 NBE 用作介体时，通过 Catellani 反应以中等至优异的产率合成芴酮，该反应涉及芳基碘化物的连续邻位-C–H 芳基化和本身脱羧酰化。使用氧杂降冰片二烯 (ONBD) 代替 NBE 可以通过逆狄尔斯-阿尔德反应组装二苯并[ a , c ]环庚烯酮，而不是释放 ONBD。此外，该方法的合成效用通过产品的多样化得到证明。
• Fucosidase inhibitors
  申请人：HORIZON ORPHAN LLC

  公开号：US10308607B2

  公开（公告）日：2019-06-04

  The present disclosure relates, in general, to compounds useful as inhibitors of fucosidase enzymes, and to methods and compositions for the treatment of tumors or cancers, such as liver disorders and liver tumors (e.g., hepatocellular carcinoma), with a compound as disclosed herein.

  本公开总体上涉及作为岩藻糖苷酶抑制剂的化合物，以及用本文公开的化合物治疗肿瘤或癌症，如肝脏疾病和肝脏肿瘤（如肝细胞癌）的方法和组合物。