丙二酸,[2-(苯磺酰)-2,3-丁二烯基]-2-丙烯基-,二甲基酯 | 149167-18-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 丙二酸,[2-(苯磺酰)-2,3-丁二烯基]-2-丙烯基-,二甲基酯
• 英文名称: 5,5-dicarbomethoxy-(2-phenylsulfonyl)-octa-1,2,7-triene
• 英文别名: 5,5-Dicarbomethoxy-3-(phenylsulfonyl)octa-1,2,7-triene
• CAS: 149167-18-0
• 化学式: C₁₈H₂₀O₆S
• 分子量: 364.419
• InChiKey: VFHWKHJHLZLQBF-UHFFFAOYSA-N

物化性质

• 沸点：
  505.6±50.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  95.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  丙二酸,[2-(苯磺酰)-2,3-丁二烯基]-2-丙烯基-,二甲基酯 以 苯 为溶剂， 反应 4.0h， 生成 4,4-dicarbomethoxy-1-methyl-N-methyl-2-(phenylsulfonyl)-8-oxa-9-azabicyclo<4.3.0>nonane
  参考文献：
  名称：

  Intramolecular [3+2]-cycloaddition of nitrones with allenes and alkynes

  摘要：

  The intramolecular dipolar cycloaddition reactions of allenyl and alkynyl nitrones proceed smoothly to give high yields of cycloadducts.

  DOI：

  10.1016/s0040-4039(00)60672-x
• 作为产物：
  描述：

  丙二酸二甲酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.67h， 生成 丙二酸,[2-(苯磺酰)-2,3-丁二烯基]-2-丙烯基-,二甲基酯
  参考文献：
  名称：

  Cyclization Reactions of 2,3-Bis(phenylsulfonyl)-1,3-butadiene with Various Carbanions. A [4 + 1] Anionic Annulation Approach to Phenylsulfonyl-Substituted Cyclopentenes

  摘要：

  2,3-Bis(phenylsulfonyl)-1,3-butadiene undergo es conjugate addition in the presence of carbanions giving rise to a variety of unsaturated sulfones. Reaction with lithium enolates proceeds via an allylic anionic intermediate which undergoes a subsequent elimination of phenylsulfinate anion to produce an allene. Generation of enolates from silyl enol ethers results in conjugate addition to the diene without subsequent elimination. Substituted cyclopentenyl sulfones are available via a [4 + 1] annulation reaction of the diene with various distabilized carbanions. The reaction involves a tandem addition-proton exchange-addition sequence. In the special case of 2,4-pentanedione, pyrans are formed, the isomeric identity of which depends upon the reaction conditions. 2-Alkylated 1,3-dicarbonyl compounds react with the activated diene to produce substituted allenes in high yield. Phenylsulfonyl alkenyl substituted allenes were conveniently prepared by a similar protocol and were found to serve as substrates for intramolecular [2 + 2] cycloaddition chemistry.

  DOI：

  10.1021/jo00082a015

文献信息

• Synthesis of novel bicyclic nitrogen heterocycles by the intramolecular dipolar cycloaddition reaction of nitrones with allenes and alkynes
  作者：Albert Padwa、Michael Meske、Zhijie Ni

  DOI：10.1016/0040-4020(94)00966-x

  日期：1995.1

  formed was identified as 4-methyl-2,5-endo-oxo-2,3,4,5-tetrahydro[1,4]benzoxazepin. The formation of this novel rearranged product involves an initial dipolar cycloaddition across the acetylenic π-bond to give the expected 4-isoxazoline as a transient intermediate. The next step proceeds by homolysis of the O-N linkage and this is followed by ring closure to produce an aziridine which undergoes further

  一系列烯丙基和炔基硝酮的分子内偶极环加成反应的研究已经进行。苯羟胺容易与邻-（1,2-丙二烯氧基）苯甲醛反应生成二氧杂氮杂双环[3.2.1]辛烯。还研究了2-（1,2-丙炔氧基）苯甲醛与N-甲基羟胺的分子内3 + 2-环加成反应。在这种情况下，形成的主要环加合物被鉴定为4-甲基-2,5-内-oxo-2,3,4,5-四氢[1,4]苯并x庚因。这种新颖的重排产物的形成涉及跨越乙炔π键的初始偶极环加成，以产生预期的4-异恶唑啉作为过渡中间体。下一步通过ON键的均质化进行，然后进行环闭合以产生氮丙啶，该氮丙啶经历进一步的CC键裂解。借助于邻-醌甲基化物中间体将所得的甲亚胺叶立德转化为最终的重排产物。还发现苯磺酰基活化的烯与烷基羟胺反应得到硝酮，该硝酮与相邻的π键进行环加成反应，得到所得的双环氮杂环。
• Periselectivity in the base-catalyzed intramolecular [2+2]-cycloaddition reaction of 3-phenylsulfonyl-substituted propynes
  作者：Albert Padwa、Helmut Lipka、Scott H Watterson

  DOI：10.1016/0040-4039(95)00860-f

  日期：1995.6

  Phenylsulfonyl-substituted allenes containing a tethered π-bond are conveniently prepared reagents that can serve as substrates for intramolecular [2+2]-cycloaddition chemistry.

  含有束缚的π键的苯磺酰基取代的烯丙基是方便制备的试剂，可以用作分子内[2 + 2]-环加成化学的底物。
• Rhodium(I)-Catalyzed Intramolecular Pauson−Khand-Type [2 + 2 + 1] Cycloaddition of Allenenes
  作者：Fuyuhiko Inagaki、Chisato Mukai

  DOI：10.1021/ol0600990

  日期：2006.3.1

  The novel [RhCl(CO)(2)](2)-catalyzed [2 + 2 + 1] cycloaddition of allenenes leading to the bicyclo[4.3.0]non-1(9)-en-8-one as well as the bicyclo-[5.3.0]dec-1(10)-en-9-one skeletons has been developed. This method also provides a new procedure for the construction of the bicyclo[4.3.0]non-1(9)-en-8-one skeleton having an alkyl appendage at the ring juncture, which was hardly attained in a satisfactory yield by the Pauson-Khand reaction of the corresponding enynes.
• Peri and stereoselectivity effects in the intramolecular [2+2]-cycloaddition reaction of phenylsulfonyl-substituted allenes
  作者：Albert Padwa、Michelle A. Filipkowski、Michael Meske、Scott H. Watterson、Zhijie Ni

  DOI：10.1021/ja00062a054

  日期：1993.5
• [3+2]-ANIONIC ELECTROCYCLIZATION USING 2,3-BIS(PHENYLSULFONYL)-1,3-BUTADIENE: trans-4,7,7-TRICARBOMETHOXY-2-PHENYLSULFONYLBICYCLO[3.3.0]OCT-1-ENE
  作者：Padwa, Albert、Watterson, Scott H.、Ni, Zhijie

  DOI：10.15227/orgsyn.074.0147

  日期：——