2,2'thiobis(3-(p-chlorophenyl)-1-phenylprop-2-en-1-one) | 242133-10-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2,2'thiobis(3-(p-chlorophenyl)-1-phenylprop-2-en-1-one)
• 英文别名: (Z,Z)-2,2'-thiobis(3-(4-chlorophenyl)-1-phenylprop-2-en-1-one)；(Z)-3-(4-chlorophenyl)-2-[(Z)-1-(4-chlorophenyl)-3-oxo-3-phenylprop-1-en-2-yl]sulfanyl-1-phenylprop-2-en-1-one
• CAS: 242133-10-4
• 化学式: C₃₀H₂₀Cl₂O₂S
• 分子量: 515.46
• InChiKey: HCUWVWLYCUWZAW-RSSRHXQMSA-N

物化性质

• 沸点：
  683.2±55.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2'thiobis(3-(p-chlorophenyl)-1-phenylprop-2-en-1-one) 在 乙酸铵 作用下， 反应 0.17h， 以76%的产率得到2-[(5Z)-5-(p-chlorobenzylidene)-2-(p-chlorophenyl)-2,5-dihydro-4-phenylthiazol-2-yl]-1-phenylethanone
  参考文献：
  名称：

  一种新颖的四组分串联方案，用于立体选择性合成高度官能化的噻唑

  摘要：

  在无溶剂微波辐射下，双（芳酰基甲基）硫化物与芳香醛和乙酸铵的摩尔比为1：2：1的反应主要产生一系列噻唑，即1-芳基-2- [5（Z）- 5-芳基亚甲基-2，4-二芳基-2，5-二氢噻唑-2-基]乙炔立体选择性地。该反应大概是通过Knoevenagel缩合反应-Michael加成-环缩合反应-开环-闭环Michael加成反应发生的。在上述转化中，（Z，Z）-2,2'-硫代双（1,3-二芳基丙-2-烯-1-酮）的中间体通过在溶剂-乙酸铵中与乙酸铵反应后转化为噻唑来证明。免费微波照射。

  DOI：

  10.1016/j.tet.2007.07.040
• 作为产物：
  描述：

  硫化双(苯甲酰甲基) 、 4-氯苯甲醛 生成 2,2'thiobis(3-(p-chlorophenyl)-1-phenylprop-2-en-1-one)
  参考文献：
  名称：

  摘要：

  The X-ray crystal structures of 2,2'.-thio- and 2,2'-sulfonylbis(1,3-diarylprop-2-en-1-ones) are detennined [1: 2,2'-thiobis(3 -(p-chlorophenyl)- 1 -phenylprop-2-en-1-one), C30H20Cl2O2S, space group C2/c, a = 14.275(3), b = 6.280(1), c = 26.533(5) Angstrom, beta = 94.55(3)degrees, Z' = 1/2; 2: 2,2'-sulfonylbis(1,3-diphenylprop-2-en-1-one), C30H22O4S, space group P (1) over bar, a = 9.652(l), b = 12.044(1), c = 12.182(l) Angstrom, alpha = 61.985(6), beta = 77.511(5), gamma = 74.340(6)degrees, Z' = 1; 3: 2,2'-sulfonylbis(3-(p-chlorophenyl)-1-phenylprop-2-en- 1-one), C30H20Cl2O4S, space group P (1) over bar a = 8.294(1), b = 13.175(2), c = 13.470(1) Angstrom, alpha = 62.870(9), beta = 83.796(7), gamma = 85.282(8)degrees, Z' = 1]. The C=C double bonds are all clearly defined. The sulfide 1 crystallizes on a crystallographic twofold axis, leading to a symmetric molecular conformation. The sulfones 2 and 3 crystallize on general positions, with different and irregular conformations.

  DOI：

  10.1023/a:1013795006690

文献信息

• Facile domino reactions for the stereoselective assembly of highly functionalized bis-(trans-2,3-dihydrofuranyl) sulfides
  作者：Beer Mohamed Vinosha、Subbu Perumal、Subbiah Renuga、Abdulrahman I. Almansour

  DOI：10.1016/j.tetlet.2013.03.088

  日期：2013.5

  facile stereoselective synthesis of a series of nineteen novel bis-(trans-2,3-dihydrofuranyl) sulfides from the reaction of (Z,Z)-2,2′-thiobis(1,3-diarylprop-2-en-1-ones) with substituted phenacyl bromides and pyridine in the presence of K2CO3 in acetonitrile via domino reactions is described. This transformation presumably occurs via pyridinium salt formation/ylide generation/Michael addition/intramolecular

  从（Z，Z）-2,2'-硫代双（1,3-二芳基丙-2-烯-1）反应中轻松合成一系列十九种新型双-（反--2,3-二氢呋喃基）硫化物描述了在乙腈中通过多米诺反应在K 2 CO 3存在下用取代的苯甲酰基溴和吡啶制得的α-酮。这种转化大概是通过吡啶鎓盐的形成/内鎓盐的生成/迈克尔加成/分子内的多米诺骨牌序列发生的，涉及在单个步骤中形成两个C-C和两个C-O键和四个立体中心，而完全的立体选择性仅提供一个非对映异构体。
• Novel Domino Reactions of (<i>Z</i>,<i>Z</i>)-2,2′-Thiobis(1,3-diarylprop-2-en-1-ones) with Acetylacetone and Ethyl Acetoacetate: Stereoselective Synthesis of Highly Functionalized Dihydrofurans
  作者：Beer Mohamed Vinosha、Subbiah Renuga、Michael Gnanadeebam、Subbu Perumal、Antonin Lycka

  DOI：10.1080/00397910802664236

  日期：2009.7.7

  Abstract The domino reactions of (Z,Z)-2,2′-thiobis(1,3-diarylprop-2-en-1-ones) with acetylacetone and ethyl acetoacetate in the presence of sodium ethoxide afforded the corresponding 4,5-dihydrofurans stereoselectively in moderate yields presumably via a Michael addition–enolization–displacement sequence.

  摘要 (Z,Z)-2,2'-硫代双(1,3-diarylprop-2-en-1-ones) 与乙酰丙酮和乙酰乙酸乙酯在乙醇钠存在下的多米诺反应得到相应的 4,5-大概是通过迈克尔加成-烯醇化-置换序列以中等产率立体选择性地生成二氢呋喃。
• Stereoselective Synthesis of Polyfunctionalized Nitrothianes: Enhancement of Stereoselectivity by Microwaves
  作者：Beermohamed Vinosha、Subbiah Renuga、Subbu Perumal、Packianathan Thomas Muthiah、Kaliyaperumal Thanigaimani

  DOI：10.1080/00397911.2012.683970

  日期：2013.7.18

  The Michael addition of nitromethane to (Z,Z)-2,2-thiobis(1,3-diarylprop-2-en-1-ones) in the presence of NaOEt in dimethylformamide (DMF)/alcohol under thermal conditions affords a diastereomeric mixture of 2a,6e-diaroyl-3a,5e-diaryl-4e-nitrothianes and 2e,6e-diaroyl-3e,5e-diaryl-4e-nitrothianes with a dr of approximate to 3:1/4:1 respectively. This reaction under microwave irradiation in DMF/alcohol afforded solely 2a,6e-diaroyl-3a,5e-diaryl-4e-nitrothianes, disclosing enhancement of stereoselectivity by microwaves. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.
• A novel four-component tandem protocol for the stereoselective synthesis of highly functionalised thiazoles
  作者：Subbiah Renuga、Michael Gnanadeebam、Beer Mohamed Vinosha、Subbu Perumal

  DOI：10.1016/j.tet.2007.07.040

  日期：2007.10

  aromatic aldehydes and ammonium acetate in 1:2:1 molar ratio under solvent-free microwave irradiation afforded predominantly a series of thiazoles, viz., 1-aryl-2-[5(Z)-5-arylmethylidene-2,4-diaryl-2,5-dihydrothiazol-2-yl]ethanones stereoselectively. This reaction presumably occurs via a Knoevenagel condensation–Michael addition–cyclocondensation–ring opening–ring closing Michael addition sequence

  在无溶剂微波辐射下，双（芳酰基甲基）硫化物与芳香醛和乙酸铵的摩尔比为1：2：1的反应主要产生一系列噻唑，即1-芳基-2- [5（Z）- 5-芳基亚甲基-2，4-二芳基-2，5-二氢噻唑-2-基]乙炔立体选择性地。该反应大概是通过Knoevenagel缩合反应-Michael加成-环缩合反应-开环-闭环Michael加成反应发生的。在上述转化中，（Z，Z）-2,2'-硫代双（1,3-二芳基丙-2-烯-1-酮）的中间体通过在溶剂-乙酸铵中与乙酸铵反应后转化为噻唑来证明。免费微波照射。
• ——
  作者：M. Gnanadeepam、S. Selvaraj、Antoine M.M. Schreurs、Jan Kroon、Thomas Steiner、S. Perumal

  DOI：10.1023/a:1013795006690

  日期：——

  The X-ray crystal structures of 2,2'.-thio- and 2,2'-sulfonylbis(1,3-diarylprop-2-en-1-ones) are detennined [1: 2,2'-thiobis(3 -(p-chlorophenyl)- 1 -phenylprop-2-en-1-one), C30H20Cl2O2S, space group C2/c, a = 14.275(3), b = 6.280(1), c = 26.533(5) Angstrom, beta = 94.55(3)degrees, Z' = 1/2; 2: 2,2'-sulfonylbis(1,3-diphenylprop-2-en-1-one), C30H22O4S, space group P (1) over bar, a = 9.652(l), b = 12.044(1), c = 12.182(l) Angstrom, alpha = 61.985(6), beta = 77.511(5), gamma = 74.340(6)degrees, Z' = 1; 3: 2,2'-sulfonylbis(3-(p-chlorophenyl)-1-phenylprop-2-en- 1-one), C30H20Cl2O4S, space group P (1) over bar a = 8.294(1), b = 13.175(2), c = 13.470(1) Angstrom, alpha = 62.870(9), beta = 83.796(7), gamma = 85.282(8)degrees, Z' = 1]. The C=C double bonds are all clearly defined. The sulfide 1 crystallizes on a crystallographic twofold axis, leading to a symmetric molecular conformation. The sulfones 2 and 3 crystallize on general positions, with different and irregular conformations.