N-(tert-butoxycarbonyl)-9-thioacridone | 1206461-96-2

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(tert-butoxycarbonyl)-9-thioacridone
• 英文别名: tert-butyl 9-thioxoacridine-10(9H)-carboxylate；Tert-butyl 9-sulfanylideneacridine-10-carboxylate
• CAS: 1206461-96-2
• 化学式: C₁₈H₁₇NO₂S
• 分子量: 311.404
• InChiKey: PPDPLMSPRYLLTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-9-thioacridone 在 三(4-甲氧苯基)膦 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 21.0h， 生成
  参考文献：
  名称：

  An unexpected bidirectional molecular rotor from unidirectional molecular motor via a stereoselective enamine-imine tautomerization process

  摘要：

  Developing stereoselective synthetic method is very important to access chiral molecular devices. We herein demonstrate how a proton initiated stereoselective enamine-imine tautomerization converts a molecular motor into a simple rotor with high diastereoselectivity (>20:1 dr). NMR and X-ray crystallography were used to elucidate the structures of both the motor and rotor unambiguously. The activated motion of the rotor about its central single bond was studied from variable temperature NMR (293423 K) and DFT calculations provide evidence of the origin of diastereoselectivity of enamine-imine tautomerization as well as the rotor dynamics with barrier as high as 39.3 kcal/mol. Results from our work may benefit future design towards stereocontrolled and adaptive molecular machines. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2020.152373
• 作为产物：
  描述：

  吖啶酮 在 劳森试剂 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 7.0h， 生成 N-(tert-butoxycarbonyl)-9-thioacridone
  参考文献：
  名称：

  An unexpected bidirectional molecular rotor from unidirectional molecular motor via a stereoselective enamine-imine tautomerization process

  摘要：

  Developing stereoselective synthetic method is very important to access chiral molecular devices. We herein demonstrate how a proton initiated stereoselective enamine-imine tautomerization converts a molecular motor into a simple rotor with high diastereoselectivity (>20:1 dr). NMR and X-ray crystallography were used to elucidate the structures of both the motor and rotor unambiguously. The activated motion of the rotor about its central single bond was studied from variable temperature NMR (293423 K) and DFT calculations provide evidence of the origin of diastereoselectivity of enamine-imine tautomerization as well as the rotor dynamics with barrier as high as 39.3 kcal/mol. Results from our work may benefit future design towards stereocontrolled and adaptive molecular machines. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2020.152373

文献信息

• Generation of “Sumanenylidene”: A Ground‐State Triplet Carbene on a Curved π‐Conjugated Periphery
  作者：Yumi Yakiyama、Yufeng Wang、Sayaka Hatano、Manabu Abe、Hidehiro Sakurai

  DOI：10.1002/asia.201801802

  日期：2019.5.15

  experimentally and theoretically that the ground state of compound 2 was a triplet state and that its singlet–triplet energy gap (ΔEST) was similar to that in fluorenylidene. The curved structure of compound 2 led to slightly better spin delocalization over the two adjacent aromatic rings than in planar systems, because of the unpaired spins on the σ and π orbitals. Synthetic application of the carbene

  我们已经观察到sumanenylidene的（产生2），二价，在sumanene（的苄基位置中性-碳物种1）。我们还从实验和理论上澄清了化合物2的基态为三重态，其单重态-三重态能隙（ΔE ST）与芴基类似。由于在σ和π轨道上不成对的自旋，化合物2的弯曲结构导致在两个相邻的芳环上的自旋离域比在平面系统中稍好。卡宾前体重氮苏曼烯的合成应用（5）中发现了多种硫代羰基化合物，可用于制备直接偶联于Suanene（1）部分的四取代烯烃化合物（例如，含有强电子给体单元）。
• A fluorenylidene-acridane that becomes dark in color upon grinding – ground state mechanochromism by conformational change
  作者：Tsuyoshi Suzuki、Hiroshi Okada、Takafumi Nakagawa、Kazuki Komatsu、Chikako Fujimoto、Hiroyuki Kagi、Yutaka Matsuo

  DOI：10.1039/c7sc03567e

  日期：——

  using alkyl tosylate or triflate. FAs were characterized by NMR, UV-vis absorption and photoluminescence spectroscopy, theoretical calculation, cyclic voltammetry, and powder and single-crystal X-ray analyses. The color and folded/twisted conformation of the FAs were changed by the choice of substituent on the nitrogen atom, physical state (solution or solid), and morphology (crystalline or amorphous)

  我们报告了由亚芴基ac啶酮（FAs）的构象变化（折叠和扭曲的构象异构体之间）控制的机械变色颜色变化。具有四个的FA ñ -烷基（甲基，乙基，Ñ丁基和Ñ辛基）的合成经由diazofluorene和亲电的巴顿凯洛格反应N-叔丁氧基羰基硫代吖啶酮，所述的脱保护叔-丁氧基羰基产生芴基ac啶，并且在氮原子上的烷基化是使用甲苯磺酸烷基酯或三氟甲磺酸酯进行的。FAs的特征在于NMR，UV-vis吸收和光致发光光谱，理论计算，循环伏安法以及粉末和单晶X射线分析。通过选择氮原子上的取代基，物理状态（溶液或固体）和形态（晶体或无定形），可以改变FA的颜色和折叠/扭曲结构。N的研磨-使用玛瑙研钵的甲基FA固体导致形态从结晶态变为无定形，从而导致构象从折叠的构象变为扭曲的构象，而机械变色的颜色从黄变为深绿色。通过溶剂蒸气暴露（氯仿）进行相反的颜色变化，以及折叠的构象物的形态和构象变化。扭曲和折叠的构象异构体分别显
• アクリジン系化合物およびこれを用いた有機薄膜デバイス
  申请人：ＪＮＣ株式会社

  公开号：JP2016132642A

  公开（公告）日：2016-07-25

  【課題】 有機薄膜デバイスの性能を向上させることができる、電荷受容性を制御可能な有機半導体化合物を提供する。【解決手段】 電子供与性を有する少なくとも１つのアクリジン系骨格と、例えばフルオレン骨格などの電子受容性を有する少なくとも１つの骨格とから形成されるアクリジン系化合物により、有機薄膜デバイスの性能を向上させる。【選択図】なし

  【问题】提供可以控制电荷接受性，从而提高有机薄膜器件性能的有机半导体化合物。 【解决方法】使用至少具有一个丙烯酰胺骨架和至少一个电子受体骨架（例如芴骨架）的丙烯酰胺类化合物，可以提高有机薄膜器件的性能。 【选择图】无。
• Ultrafast Light-Driven Nanomotors Based on an Acridane Stator
  作者：Artem A. Kulago、Emile M. Mes、Martin Klok、Auke Meetsma、Albert M. Brouwer、Ben L. Feringa

  DOI：10.1021/jo902207x

  日期：2010.2.5

  A series Of Molecular motors featuring a symmetrical acridane stator is reported. Photochemical and thermal isomerization experiments confirm that this stator, in combination with a thiopyran rotor, results in molecular rotary motion in which the rate-determining thermal helix inversion proceeds effectively only at temperatures above 373 K. The introduction of a cyclopentanylidene rotor unit results in a decrease in steric hindrance with respect to the stator, and as a consequence, a 10(12)-fold increase in the rate of thermal helix inversion is observed. Nanosecond transient absorption spectroscopy allows for the thermal processes to be followed accurately at ambient temperature. The rotary motor is shown to be able to operate at 0.5 MHz rotational frequencies Under optimal conditions.