(-)-(4S,5S)-4,5-diphenyl-1,3-dioxolan-2-one | 163438-21-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (-)-(4S,5S)-4,5-diphenyl-1,3-dioxolan-2-one
• 英文别名: trans-1,2-diphenylethylene carbonate；trans-4,5-diphenyl-(1,3-dioxolan-2-one)；(4S,5S)-4,5-diphenyl-1,3-dioxolan-2-one
• CAS: 163438-21-9
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: IMISELAHEPXOAQ-KBPBESRZSA-N

物化性质

• 沸点：
  427.7±45.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(4S,5S)-4,5-diphenyl-1,3-dioxolan-2-one 在 potassium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以90%的产率得到(S,S)-(-)-氢化苯偶姻
  参考文献：
  名称：

  Influence of Temperature and Pressure on Cyclic Carbonate Synthesis Catalyzed by Bimetallic Aluminum Complexes and Application to Overall syn-Bis-hydroxylation of Alkenes

  摘要：

  The effect of moderate temperatures (22-100 degrees C) and pressures (1-10 bar) on the synthesis of cyclic carbonates from epoxides and carbon dioxide catalyzed by a combination of bimetallic aluminum complexes and tetrabutylammonium bromide is investigated. The combined bimetallic complex and tetrabutylammonium bromide catalyst system is shown to be an order of magnitude more active than the use of tetrabutylammonium bromide alone at all temperatures and pressures studied. At the higher temperatures and pressures used, disubstituted epoxides become substrates for the reaction and it is shown that reactions proceed with retention of the epoxide stereochemistry. This allowed a route for the overall syn-bis-hydroxylation of alkenes to be developed without the use of hazardous metal based reagents. At higher pressures it is also possible to use compressed air as the carbon dioxide source.

  DOI：

  10.1021/jo302317w
• 作为产物：
  描述：

  二氧化碳 、 (S,S)-trans-stilbene oxide 在 C₂₁H₃₅Al₂FeN₃ 、 四丁基碘化铵 作用下， 以 neat (no solvent) 为溶剂， 90.0 ℃ 、850.01 kPa 条件下， 反应 24.0h， 以20%的产率得到(-)-(4S,5S)-4,5-diphenyl-1,3-dioxolan-2-one
  参考文献：
  名称：

  用于将 CO2 催化固定成环状碳酸盐的单核和双核不对称铝胍

  摘要：

  一组三取代胍配体L 1 H 2 – L 4 H 2具有通式 ( i PrHN) 2 CNR (R = Ph (L 1 H 2 ), R = 2,4,6-Me 3 C 6 H 2 ( L 2 H 2 ), R = p -BrC 6 H 4 (L 3 H 2 ), R = (C 5 H 4 )Fe(C 5 H 5 ), Fc (L 4 H 2 ))) 用于合成一系列单核和双核不对称甲基铝胍化合物（(L 2 H)AlMe 2 ( 1 ), (L 4 H)AlMe 2 ( 2 ), (L 1 )Al 2 Me 4 ( 3 ), (L 2 )Al 2 Me 4 ( 4 ), (L 3 )Al 2 Me 4 ( 5 ), (L 4 )Al 2 Me 4 ( 6 ), (L 1 H) 2 AlMe (7 )、(L 2 H) 2 AlMe ( 8 ) 和 (L 4 H) 2 AlMe ( 9 )) 经核磁共振波谱

  DOI：

  10.1021/acs.organomet.1c00319

文献信息

• Coordination chemistry of ester-functionalized cp ligands: synthesis and catalytic activity of [Rh{CpCO2(CHPh)2OH}(NBD)] and [Rh{CpCO2(CH2)3OH}(NBD)]
  作者：Luigi Busetto、M.Cristina Cassani、Rita Mazzoni、Piero Frediani、Eleonora Rivalta

  DOI：10.1016/j.jorganchem.2004.04.010

  日期：2004.7

  Two new sodium hydroxyalkoxycarbonylcyclopentadienide salts Na[rac-CpCO2(CHPh)2OH] (1) and Na[(2S,3S)-CpCO2(CHPh)2OH] (2) were prepared by reaction of NaCp with the five-membered cyclic carbonates cis-4,5-diphenyl-1,3-dioxolan-2-one and (4S,5S)-4,5-diphenyl-1,3-dioxolan-2-one. The reaction of these salts with [Rh(NBD)Cl]2 gave [Rhrac-CpCO2(CHPh)2OH}(NBD)] (3) and (−)-[Rh(2S,3S)-CpCO2(CHPh)2OH}(NBD)]

  通过将NaCp与五种五烷基酚反应，制得两种新的羟基烷氧基羰基环戊二烯酸钠钠盐[ rac- CpCO 2（CHPh）2 OH]（1）和Na [（2S，3S）-CpCO 2（CHPh）2 OH]（2）。元环状碳酸酯顺-4，5-二苯基-1，3-二氧戊环-2-一和（4S，5S）-4，5-二苯基-1，3-二氧戊环-2-一。这些盐与[Rh（NBD）Cl] 2反应，得到[Rh rac -CpCO 2（CHPh）2 OH}（NBD）]（3）和（-）-[Rh （2 S，3 S）-CpCO 2（CHPh）2 OH}（NBD）]（4），已研究了其在己烯-1-烯和苯乙烯加氢甲酰化反应中的催化活性，并与先前报道的铑配合物[Rh CpCO 2（ CHR）2 OH}（NBD）]（R = H，Me）。此外，我们还讨论了有关这些配合物在相同底物氢化中的行为的一些初步结果。还研究了NaCp对六元环状碳酸酯1,3-二氧
• Synthesis of Cyclic Carbonates Catalysed by Chromium and Aluminium Salphen Complexes
  作者：José A. Castro-Osma、Michael North、Xiao Wu

  DOI：10.1002/chem.201504305

  日期：2016.2.5

  Chromium and aluminium salphen complexes have been found to display remarkable catalytic activity in the synthesis of cyclic carbonates from a range of epoxides and carbon dioxide. The Al(salphen) complex is more reactive towards terminal epoxides at ambient temperature and pressure, whereas the Cr(salphen) complex exhibits higher catalytic activity towards more challenging internal epoxides at elevated

  已发现铬和铝二烯化合物在由多种环氧化物和二氧化碳合成环状碳酸酯中显示出显着的催化活性。Al（salphen）络合物在环境温度和压力下对末端环氧化物更具反应性，而Cr（salphen）络合物在升高的温度和压力下对更具挑战性的内部环氧化物表现出更高的催化活性。
• Reaction of 1,2-Cyclic Sulfites with Some Soft Nucleophiles. Formation of Enantiomerically Pure gamma-Lactones.
  作者：Kirsten Nymann、John S. Svendsen、Eli Ranes、Jaroslav Riha、Eugen Mesaros、Alin Mihis、Inger Søtofte、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0338

  日期：——

  The reaction between 1,2-cyclic sulfites and soft carbon centered nucleophiles has been investigated. For monosubstituted cyclic sulfites, the main products were gamma-lactones or acetoxy esters. For 1,2-disubstituted cyclic sulfites. cyclopropanes. carbonate and dioxolanes were the main products, A mechanistic rationale for the product formation is presented.
• Chemical Synthesis and Biological Evaluation of C-2 Taxoids
  作者：K. C. Nicolaou、J. Renaud、P. G. Nantermet、E. A. Couladouros、R. K. Guy、W. Wrasidlo

  DOI：10.1021/ja00114a005

  日期：1995.3

  An efficient, general method for the synthesis of 1,2-hydroxy esters by regioselective nucleophilic opening of 1,2-cyclic carbonate systems has been developed. A reliable and practical route giving access to the taxoid carbonate 2 from the readily available 10-deacetylbaccatin III (13) has been established. Nucleophilic opening of the carbonate 2 with a variety of nucleophiles provided a number of novel C-2 Taxols. Water-soluble taxoid onium salts (e.g., 31e, 31n, 32, and 34b) were also synthesized and studied. A selected number of taxoids were subjected to cytotoxicity and tubulin polymerization assays as well as in vivo studies. The results of these studies are reported herein.
• Nicolaou, Kyriacos Costa; Couladouros, E. A.; Nantermet, P. G., Angewandte Chemie, 1994, vol. 106, # 15/16, p. 1669 - 1671
  作者：Nicolaou, Kyriacos Costa、Couladouros, E. A.、Nantermet, P. G.、Renaud, J.、Guy, Rodney Kiplin、Wrasidlo, Wolfgang

  DOI：——

  日期：——