3,5-dihydro-1H-thieno<3,4-c>pyrrole 2,2-dioxide | 144425-36-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3,5-dihydro-1H-thieno<3,4-c>pyrrole 2,2-dioxide
• 英文别名: 3,5-dihydro-1H-thieno[3,4-c]pyrrole 2,2-dioxide；3,5-Dihydro-1H-thieno[3,4-c]pyrrol-2,2-dioxid；β''-sulfolenopyrrole
• CAS: 144425-36-5
• 化学式: C₆H₇NO₂S
• 分子量: 157.193
• InChiKey: SQBIKFLDAFKKSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  482.0±45.0 °C(Predicted)
• 密度：
  1.519±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-dihydro-1H-thieno<3,4-c>pyrrole 2,2-dioxide 在 Montmorillonite clay K-10 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Porphodimethylidenes from porphyrin-fused 3-sulfolenes—versatile porphyrin dienes for cycloadditions

  摘要：

  卟啉中的一个吡咯上含有δ-融合的 3-亚硫基，可作为卟吩二甲叉前体，用于各种 DielsâAlder 环加成反应。

  DOI：

  10.1039/a901446b
• 作为产物：
  描述：

  3,5-Dihydro-1H-thieno[3,4-c]pyrrolcarbonsaeure-2,2-dioxide 在 三氟乙酸 作用下， 反应 0.33h， 以56%的产率得到3,5-dihydro-1H-thieno<3,4-c>pyrrole 2,2-dioxide
  参考文献：
  名称：

  摘要：

  The efficient preparation of the symmetric tetrasulfolenoporphyrin 1 is reported, which shows good solubility in a variety of solvents. In 1, four sulfone groups that symmetrically bridge the eight methylene groups in beta-position at the pyrrole rings provide four sulfolene (= 2,5-dihydrothiophene 1,1-dioxide) units which are prone to cleavage by thermally induced extrusion of sulfur dioxide. The tetrasulfolenoporphyrin, accordingly, is indicated to lend itself to specific and multiple refunctionalization by the replacement of the sulfone groups by other functionalities in SO(2) extrusion/cycloaddition sequences. The predicted reactivity and the potential of a zinc complex of the tetrasulfolenoporphyrin as a reactive porphyrin module (see 5b) is tested in exploratory experiments. To this end, thermolysis of the tetrasulfolenoporphyrinatozinc 5b in dichlorobenzene solution (at 140 degrees) and in the presence of [5,6]fullerene-C(60)-I(h) gives the (fullereno-porphyrinato)zinc 6 still having three sulfolene units and a 'diagonal' (difullerenoporphyrinato)zinc 7 that still has two sulfolene units, in 14 and in 43% yield, respectively.

  DOI：

  10.1002/(sici)1522-2675(20000315)83:3<583::aid-hlca583>3.0.co;2-a

文献信息

• New building blocks, 3,5-dihydro-1H-thieno[3,4-c]pyrrole 2,2-dioxides; Preparation and their Diels-Alder reaction with dimethyl acetylenedicarboxylate
  作者：Kaori Ando、Mutsuo Kankake、Takayoshi Suzuki、Hiroaki Takayama

  DOI：10.1016/0040-4020(94)00968-z

  日期：1995.1

  5-dihydro-1H-thieno[3,4-c]pyrrole 2,2-dioxides 3, have been prepared by the oxidation of their corresponding pyrroline derivatives 4 with DDQ or Chemical MnO2. The Diels-Alder reaction of 3 with dimethyl acetylenedicarboxylate gave new types of compunds: 7-aza-2,3-dimethylenenorbornenes A, the 1:2 adducts B, 1a,3a,6,9-tetrahydrobenz[g]indoles C, and dihydroindolosulfolene D depending on the reaction conditions and the

  通过用DDQ或化学MnO 2氧化相应的吡咯啉衍生物4，可以制备新的结构单元3,5-二氢-1 H-噻吩并[3,4- c ]吡咯2，2-二氧化物3。3与乙酰二羧酸二甲酯的Diels-Alder反应产生了新的化合物：7-氮杂-2,3-二亚甲基降冰片烯A，1：2加合物B，1a，3a，6,9-四氢苯并[ g ]吲哚C和dihydroindolosulfolene d取决于反应条件和ñ -取代基。3与二（叔）的反应还描述了-丁基磺酰基）乙炔。
• New building blocks, 3,5-dihydro-1H-thieno[3,4-c]pyrrole 2,2-dioxides; preparation and their Diels–Alder reaction with dimethyl acetylenedicarboxylate
  作者：Kaori Ando、Mutuo Kankake、Takayoshi Suzuki、Hiroaki Takayama

  DOI：10.1039/c39920001100

  日期：——

  New building blocks, 3,5-dihydro-1H-thieno[3,4-c]pyrrole 2,2-dioxides 1, have been prepared and react with dimethyl acetylenedicarboxylate to give new types of compound: 7-aza-2,3-dimethylenenorbornene A, the 1:2 adduct B, 1a,3a,6,9-tetrahydrobenz[g]indole C, and dihydroindolosulfolene D depending on the reaction conditions and the N-substituent.

  已制备新的结构单元3,5-二氢-1 H-噻吩并[3,4- c ]吡咯2,2-二氧化物1，并与乙酰二羧酸二甲酯反应生成新型化合物：7-氮杂-2，根据反应条件和N-取代基，3-二亚甲基降冰片烯A，1：2加合物B，1a，3a，6,9-四氢苯并[ d ]吲哚C和二氢吲哚并丁二酚D。
• Symmetrical tetra-β″-sulfoleno-<i>meso</i>-aryl-porphyrins — synthesis, spectroscopy and structural characterization
  作者：Srinivas Banala、Klaus Wurst、Bernhard Kräutler

  DOI：10.1142/s1088424613501204

  日期：2014.1

  We report here the preparation (in "one-pot") of a tetra-β″-sulfoleno-meso-aryl-porphyrin in about 80% yield by using an optimized modification of Lindsey's variant of the Adler–Longo approach. The Zn ( II )-, Cu ( II )- and Ni ( II )-complexes of the symmetrical porphyrin were prepared and characterized spectroscopically. Crystal structures of the fluorescent Zn ( II )- and of the non-fluorescent Ni ( II )-tetra-β″-sulfoleno-meso-aryl-porphyrinates showed the highly substituted porphyrin ligands to be nearly perfectly planar. The Zn ( II )-complex of this porphyrin has been used as a thermal precursor of a reactive diene, and — formally — of lateral and diagonal bis-dienes, of a tris-diene and of a tetra-diene, which all underwent [4 + 2]-cycloaddition reactions in situ with a range of dienophiles. Thus, the tetra-β″-sulfoleno-meso-aryl-porphyrin and its metal complexes represent reactive building blocks, "programmed" for the syntheses of symmetrical and highly functionalized porphyrins.

  我们在此报告，通过对 Lindsey 的 Adler-Longo 方法变体进行优化修改，以约 80% 的收率（"一锅 "法）制备了四-β″-亚磺酰基芳基卟啉。制备了对称卟啉的 Zn ( II )-、Cu ( II )- 和 Ni ( II )- 复合物，并对其进行了光谱学表征。荧光 Zn ( II )- 和非荧光 Ni ( II )- 四-β″-亚磺酰基芳基卟啉的晶体结构显示，高度取代的卟啉配体几乎是完全平面的。这种卟啉的 Zn ( II )-络合物已被用作活性二烯的热前体，并正式用作侧向和对角双二烯、三二烯和四二烯的热前体，它们都在原位与一系列二烯烃发生了[4 + 2]-环加成反应。因此，四-β″-亚磺酰基芳基卟啉及其金属复合物代表了活性构件，是合成对称和高功能化卟啉的 "程序化 "产物。
• Corroles programmed for regioselective cycloaddition chemistry — synthesis of a bisadduct with <font>C₆₀</font>-fullerene
  作者：Chengjie Li、Martin Fechtel、Yaqing Feng、Bernhard Kräutler

  DOI：10.1142/s108842461250054x

  日期：2012.5

  data indicated attachment of the two fullerene units at the "western," directly connected pyrrole rings. The tetrasulfoleno-corrole thus showed a remarkable preference for loss of sulphur dioxide and subsequent cycloaddition at the two "western" rings. In the difullereno-adduct, two sulfolene groups in the remaining "eastern" β,β″-disulfoleno-pyrroles still are available as "caged dienes" for further

  对称的 β,β'-四磺基咯咯咯在此被描述为高反应性咯咯-β,β'-二烯的优良选择性前体，通过环加成化学打开了通往特定 β,β'-官能化咯咯的选择性途径。β,β'-四亚砜基-咯咯是通过酸催化缩合甲苯醛和β,β'-二亚砜基-二吡咯甲烷制备的，后者是通过标准程序获得的。以 8-10% 的收率分离出结晶的深绿色 β,β'-四磺基咯咯咯。corrole 在 140 °C 和过量 C 存在下的热解60-富勒烯选择性地产生二富勒烯-考罗（> 80% 产率）。光谱数据表明两个富勒烯单元在“西部”直接连接的吡咯环上的连接。因此，四磺基-莠萝表现出对二氧化硫损失和随后在两个“西方”环上的环加成的显着偏好。在二富勒烯加合物中，剩余的“东部”β,β”-二磺基吡咯中的两个环丁砜基团仍可作为“笼式二烯”用于进一步热二烯形成，并通过 [4 + 2]-环加成连接其他基团反应。
• Sulfolenoporphyrins: synthons for refunctionalization of porphyrins
  作者：Sang Hee Lee、Kevin M. Smith

  DOI：10.1016/j.tetlet.2005.01.154

  日期：2005.3

  Using sulfolenopyrroles (4) and (11) methods are developed for the synthesis of opp- (15,18,19) and adj- (25) bis-sulfolenoporphyrins,- such compounds are useful building blocks for the refunctionalization of the porphyrin system, and readily undergo Diels-Alder cycloaddition reactions. (C) 2005 Elsevier Ltd. All rights reserved.