3,3-bis(3-phenylprop-2-yn-1-yl)pentane-2,4-dione | 96262-82-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 3,3-bis(3-phenylprop-2-yn-1-yl)pentane-2,4-dione
• 英文别名: 3,3-Bis(3-phenylprop-2-ynyl)pentane-2,4-dione；3,3-bis(3-phenylprop-2-ynyl)pentane-2,4-dione
• CAS: 96262-82-7
• 化学式: C₂₃H₂₀O₂
• 分子量: 328.411
• InChiKey: KVNYBYXPGVZKQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3-bis(3-phenylprop-2-yn-1-yl)pentane-2,4-dione 在 cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate 、 二甲基亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以93%的产率得到1,1'-(1,3-diphenyl-5,6-dihydro-4H-cyclopenta[c]furan-5,5-diyl)bis(ethan-1-one)
  参考文献：
  名称：

  Ruthenium-Catalyzed Transfer Oxygenative Cyclization of α,ω-Diynes: Unprecedented [2 + 2 + 1] Route to Bicyclic Furans via Ruthenacyclopentatriene

  摘要：

  A novel oxygen-atom-transfer process enables the catalytic [2 + 2 + 1] synthesis of bicyclic furans from alpha,omega-diynes with DMSO. [CpRu(AN)(3)]PF6 catalyzed the transfer oxygenative cyclization of diynes with aryl terminal groups, while those of diynes with alkyl terminal groups were effectively promoted by the corresponding Cp* complex. A mechanism for bicyclic furan formation via a ruthenacyclopentatriene was proposed on the basis of both experimental and theoretical studies.

  DOI：

  10.1021/ja302868s
• 作为产物：
  描述：

  1-bromo-3-phenylprop-2-yne 生成 3,3-bis(3-phenylprop-2-yn-1-yl)pentane-2,4-dione
  参考文献：
  名称：

  SCHULTE; REISCH; MOCK, Archiv der Pharmazie, 1962, vol. 295 /67, p. 627 - 639

  摘要：

  DOI：

文献信息

• A Combined Transition-Metal-Catalyzed and Photopromoted Process: Synthesis of 2,3-Fused 4-Phenylnaphthalen-1-yl Carboxylates from 1,7-Diaryl-1,6-diynes
  作者：Yoshihiko Yamamoto、Shota Mori、Masatoshi Shibuya

  DOI：10.1002/chem.201500978

  日期：2015.6.15

  2,3‐Fused 4‐phenylnaphthalen‐1‐yl carboxylates were synthesized in a step‐ and atom‐economical manner using a ruthenium‐catalyzed hydrocarboxylative cyclization of 1,7‐diaryl‐1,6‐diynes and subsequent oxidative photocyclization. The scope of this novel two‐step process was demonstrated by the construction of diverse structures from substrates with various tethers and terminal aryl groups. Late‐stage

  使用钌催化的1,7-二芳基-1,6-二炔的羧基化环化反应和随后的氧化光环化反应，以分步和原子经济的方式合成了2,3-熔融的4-苯基萘-1-基羧酸盐。这种新颖的两步法的范围由具有各种系链和末端芳基的底物的不同结构的构建证明。后期阶段C中的arylnaphthalene产物h的官能化进一步提高发达进程的合成潜力。
• A convergent formal [4 + 2] cycloaddition of 1,6-diynes and benzyl azides: construction of spiro-polyheterocycles
  作者：Ming Bao、Wei Lu、Han Su、Lihua Qiu、Xinfang Xu

  DOI：10.1039/c8ob00735g

  日期：——

  A convergent formal [4 + 2] cycloaddition reaction for the construction of structurally appealing spiro-tetrahydroquinolines has been developed, in which, a one-pot reaction is established for the in situ generation of two reagents, a cyclic alkyne and an N-aryliminium ion, from the corresponding precursors in the presence of an Au-catalyst and Brønsted acid, respectively.

  已经开发出一种收敛的正式[4 + 2]环加成反应，用于构建结构吸引人的螺-四氢喹啉，其中建立了一个一锅反应，可就地生成两种试剂，环状炔烃和N-芳基亚胺离子，分别在金催化剂和布朗斯台德酸的存在下从相应的前体中分离出来。
• Combined Experimental and Computational Study on Ruthenium(II)-Catalyzed Reactions of Diynes with Aldehydes and <i>N</i>,<i>N</i>-Dimethylformamide
  作者：Yoshihiko Yamamoto、Yuta Okude、Shota Mori、Masatoshi Shibuya

  DOI：10.1021/acs.joc.7b01229

  日期：2017.8.4

  calculations [PCM (THF) M06L/SDD-6-311++G(d,p)//B3LYP/LanL2DZ-6-31G(d)] and control experiments. The (Z)-selectivity increased when the bulkiness of the diyne terminal substituents increased. Notably, the reaction of 1,6-diynes bearing tert-butyl terminal groups with various α,β-unsaturated aldehydes exclusively afforded (Z)-dienyl ketones even at 70 °C when a cationic ruthenium complex with a smaller η5-cyclopentadienyl

  的1,6-二炔轴承用甲基端基环加成反应p -anisaldehyde使用与η阳离子钌催化剂进行5 -五甲基配位体在THF中在室温下通过最初形成的稠合的吡喃的开环，得到二烯基酮。使用钌催化剂选择性地获得了二烯基酮的（Z）-立体异构体，而先前报道的铑催化剂则产生了（E）-异构体。这些（ë） -和（Ž）-selectivities被动力学控制作为显示控制的实验，该ë / Ž（的-isomerization Ë）-二烯基酮在70°C的温度下发生10小时，以使E / Z比率接近1：1。对于钌催化剂这一特性立体选择性的来源归因于CPRU的直接开环+配位的理论计算[PCM（THF）M06L / SDD-6-311 ++ G（d的基础上吡喃复杂中间体， p）// B3LYP / LanL2DZ-6-31G（d）]和对照实验。当二炔末端取代基的体积增加时，（Z）-选择性增加。值得注意的是，即使在70°C时，
• Cp*Co(III)-Catalyzed Regioselective Synthesis of Cyclopenta[<i>b</i>]carbazoles via Dual C(sp²)–H Functionalization of 1-(Pyridin-2-yl)-indoles with Diynes
  作者：Qiuyun Li、Yanwei Wang、Bin Li、Baiquan Wang

  DOI：10.1021/acs.orglett.8b03438

  日期：2018.12.21

  Cp*Co(III)-catalyzed synthesis of cyclopenta[b]carbazoles from 1-(pyridin-2-yl)-indoles and diynes is developed. This reaction involves dual C–H activation of indoles and domino cyclizations with diynes and has excellent regioselectivity, high efficiency, a broad substrate scope, and tolerance for various functional groups. A series of cyclopenta[b]carbazole molecular scaffolds are obtained in good

  开发了Cp * Co（III）催化的1-（吡啶-2-基）-吲哚和二炔合成环戊[ b ]咔唑的方法。该反应涉及吲哚的双重C–H活化和带有二炔的多米诺环化反应，具有出色的区域选择性，高效率，广泛的底物范围以及对各种官能团的耐受性。以良好或优异的产率获得了一系列环戊[ b ]咔唑分子支架。
• Rhodium(III)-Catalyzed [2+2+2] Cyclotrimerization of Diynes with Maleic Anhydrides as Alkyne Equivalents
  作者：Takanori Matsuda、Kentaro Suzuki

  DOI：10.1002/ejoc.201500252

  日期：2015.5

  anhydrides function as synthetic equivalents of alkynes in a rhodium(III)-catalyzed reaction with 1,6-diynes to achieve a formal [2+2+2] cyclotrimerization. This approach is useful for reactions involving alkynes with low boiling points or severe ring strain. Hard-to-access [2+2+2] cycloadducts are available through this new cycloaddition strategy by employing easy-to-handle alkyne equivalents.

  取代的马来酸酐在铑 (III) 催化与 1,6-二炔的反应中用作炔烃的合成等价物，以实现正式的 [2+2+2] 环三聚反应。这种方法对于涉及低沸点或严重环应变的炔烃的反应很有用。通过采用易于处理的炔烃等价物，通过这种新的环加成策略可以获得难以获得的 [2+2+2] 环加合物。