2-(3-thienylmethylene)-1H-indene-1.3(2H)-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(3-thienylmethylene)-1H-indene-1.3(2H)-dione
• 英文别名: 2-(thiophen-3-ylmethylene)-1H-indene-1,3(2H)-dione；2-(3-Thienylmethylene)indane-1,3-dione；2-(thiophen-3-ylmethylidene)indene-1,3-dione
• 化学式: C₁₄H₈O₂S
• 分子量: 240.282
• InChiKey: LBTCAOFAELGQCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  戊二醛 、 2-(3-thienylmethylene)-1H-indene-1.3(2H)-dione 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 N,N-二异丙基乙胺 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以95%的产率得到
  参考文献：
  名称：

  Organocatalytic Synthesis of Substituted Spirocyclohexane Carbaldehydes via [4 + 2] Annulation Strategy between 2-Arylideneindane-1,3-diones and Glutaraldehyde

  摘要：

  An organocatalytic domino reaction between 2-arylideneindane-1,3-diones and glutaraldehyde has been devised that gives functionalized spirocyclohexane carbaldehydes with an all-carbon quaternary center. The reaction proceeds through a Michael/Aldol sequence in good-to-high chemical yields and with high levels of stereoselectivity (up to >95:5 dr and 99% cc) in the presence of the alpha,alpha-L-diphenylprolinol trimethylsilyl ether 3 (20 mol %) and DIPEA (20 mol %) in ether at 0 degrees C.

  DOI：

  10.1021/ol501160k
• 作为产物：
  描述：

  3-噻吩甲醛 、 1,3-茚满二酮 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以59%的产率得到2-(3-thienylmethylene)-1H-indene-1.3(2H)-dione
  参考文献：
  名称：

  Franz, Claudia; Heinisch, Gottfried; Holzer, Wolfgang, Heterocycles, 1995, vol. 41, # 11, p. 2527 - 2552

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed Enantioselective Cycloaddition of Carbonylogous 1,4-Dipoles: Efficient Access to Chiral Cyclohexanones
  作者：Barry M. Trost、Zhiwei Jiao

  DOI：10.1021/jacs.0c11535

  日期：2020.12.30

  A novel palladium-mediated carbonylogous 1,4-dipole was developed by in situ deprotonation. By using our own-developed C2-unsymmetric phosphoramidite as supporting ligand, this dipole was applied to the asymmetric synthesis of chiral cyclohexanones via a catalytic [4+2] cycloaddition. Electron-deficient allylic carbonate was used to generate the highly reactive palladium-mediated dipoles for the first

  通过原位去质子化开发了一种新型钯介导的碳基 1,4-偶极子。通过使用我们自己开发的 C2 不对称亚磷酰胺作为支持配体，该偶极子通过催化 [4+2] 环加成反应应用于手性环己酮的不对称合成。缺电子烯丙基碳酸酯首次用于生成高反应性钯介导的偶极子，并探索了各种稳定的偶极子前体以制备手性环己酮。提出了反应过程和立体化学结果的一般机制，可用于设计和预测未来的转化。
• Asymmetric Synthesis of Spiro Tetrahydrothiophene-indan-1,3-diones via a Squaramide-Catalyzed Sulfa-Michael/Aldol Domino Reaction
  作者：Dieter Enders、Suruchi Mahajan、Pankaj Chauhan、Marcus Blümel、Rakesh Puttreddy、Kari Rissanen、Gerhard Raabe

  DOI：10.1055/s-0035-1560412

  日期：——

  Abstract A new asymmetric domino sulfa-Michael/aldol reaction of 2-arylidene-1,3-indandiones with 1,4-dithiane-2,5-diol catalyzed by a sub-mol% loading of a squaramide provides a direct access to tetrahydrothiophene bearing spiro indane-1,3-dione derivatives in excellent yields and good stereoselectivities. A new asymmetric domino sulfa-Michael/aldol reaction of 2-arylidene-1,3-indandiones with 1,4-dithiane-2

  摘要 亚摩尔％的方酰胺负载催化的2-芳基-1,3-茚满二酮与1,4-二噻吩-2,5-二醇的新的不对称多米诺磺胺-迈克尔/羟醛反应可直接进入带有四氢噻吩的化合物螺环茚满-1,3-二酮衍生物，具有出色的收率和良好的立体选择性。 亚摩尔％的方酰胺负载催化的2-芳基-1,3-茚满二酮与1,4-二噻吩-2,5-二醇的新的不对称多米诺磺胺-迈克尔/羟醛反应可直接进入带有四氢噻吩的化合物螺环茚满-1,3-二酮衍生物，具有出色的收率和良好的立体选择性。
• [3+2] regioselective annulation reaction of 2-arylidene-1,3-indandiones towards synthesis of spirocyclopentenes: understanding the mechanism of γ-attack<i>vs.</i>α-attack using DFT studies
  作者：Shaik Anwar、Li-Tzu Lin、V. Srinivasadesikan、Veera Babu Gudise、Kwunmin Chen

  DOI：10.1039/d1ra07165c

  日期：——

  A [3+2] annulation protocol for the construction of functionalized spirocyclopentenes utilizing 1,3-indanedione derived benzylidene-1,3-indanedione and ethyl-2,3-butadienoate at room temperature was developed.

  开发了一种[3+2]环加成协议，利用1,3-茚二酮衍生的苯甲醛基-1,3-茚二酮和2,3-丁二烯酸乙酯在室温下构建官能化螺环戊烯。
• Brønsted Acid Tuned, Lewis Base Promoted [4 + 2] Annulation Reactions of Allenoates with Electron-Deficient Olefins
  作者：Qiu-Zhen Xi、Zhen-Jie Gan、Er-Qing Li、Zheng Duan

  DOI：10.1002/ejoc.201800917

  日期：2018.9.23

  4H‐pyran from an allenoate and an olefin demonstrates the dual roles of triethylenediamine (DABCO) in both Lewis base promoted [4 + 2] annulation and Brønsted base mediated C=C isomerization. The role of the Brønsted base could be quenched selectively with the presence of a Brønsted acid (PhCO2H).

  由烯丙酸酯和烯烃选择性形成环状的4 H-吡喃表明，三乙二胺（DABCO）在Lewis碱促进的[4 + 2]环化和Brønsted碱介导的C = C异构化中均具有双重作用。布朗斯台德碱的作用可以在布朗斯台德酸（PhCO 2 H）的存在下选择性地淬灭。
• Substrate-controlled [4+1] and [3+2] annulations of ninhydrin-derived Morita–Baylis–Hillman carbonates to access polysubstituted furans and cyclopentenes
  作者：Kai-Kai Wang、Yan-Li Li、Ya-Fei Li、Wei-Wei Yao、Lan-Xin Li、Xiao-Long He、Rongxiang Chen

  DOI：10.1039/d3cc06276g

  日期：——

  The effective and mild [4+1] annulation of ninhydrin-derived MBH carbonates with α,β-unsaturated ketones has been developed, providing a wide range of multisubstituted furans in high yields (up to 90%) with excellent β-regioselectivities. In contrast, the polysubstituted cyclopentenes bearing dispiro-bisindanedione motifs were obtained via classical [3+2] annulations by employing ninhydrin-derived

  已经开发出茚三酮衍生的 MBH 碳酸酯与 α,β-不饱和酮的有效且温和的 [4+1] 环化，以高收率（高达 90%）提供多种多取代呋喃，并具有优异的 β-区域选择性。相比之下，带有二螺-双茚满二酮基序的多取代环戊烯是在相同的催化条件下使用茚三酮衍生的MBH碳酸酯与2-亚芳基-1,3-茚满二酮通过经典的[3+2]环化获得的。此外，通过X射线衍射分析直接证实了两种环加合物的结构。