3,4-噻吩二羧酸,四氢-,二甲基酯,反- | 105526-70-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 3,4-噻吩二羧酸,四氢-,二甲基酯,反-
• 英文名称: trans-dimethyl tetrahydrothiophene-3,4-dicarboxylate
• 英文别名: dimethyl tetrahydrothiophene-3,4-dicarboxylate；(+/-)-trans-tetrahydro-thiophene-3,4-dicarboxylic acid dimethyl ester；(+/-)-trans-Tetrahydro-thiophen-3,4-dicarbonsaeure-dimethylester；dimethyl (3S,4S)-thiolane-3,4-dicarboxylate
• CAS: 105526-70-3；105850-95-1；111138-54-6
• 化学式: C₈H₁₂O₄S
• 分子量: 204.247
• InChiKey: DHKCGAJEQXUMME-WDSKDSINSA-N

物化性质

• 熔点：
  51.5-53 °C
• 沸点：
  293.8±40.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(+/-)-trans-tetrahydro-thiophene-3,4-dicarboxylic acid diethyl ester	105526-72-5	C10H16O4S	232.301

反应信息

• 作为反应物：
  描述：

  3,4-噻吩二羧酸,四氢-,二甲基酯,反- 在 吡啶 、 lithium aluminium tetrahydride 、 三氟甲磺酸三甲基硅酯 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis of 4′-thionucleosides by 1,3-dipolar cycloadditions of the simplest thiocarbonyl ylide with alkenes bearing electron-withdrawing groups

  摘要：

  Reactions of the simplest thiocarbonyl ylide with a variety of appropriate alkenes bearing electron-withdrawing substituents afforded the corresponding tetrahydrothiophenes, which could be easily elaborated into hydroxy and hydroxymethyl derivatives and then coupled with nucleobases to produce different 4 '-thionucleo sides. Particularly, alpha- and beta-anomers of 1-[3,4-bis(hydroxymethyl)tetrahydro-2-thienyl]-thymine, -cytosine, -uracil and -fluorouracil were prepared with dimethyl fumarate and maleate, while 1-[4-(hydroxymethyl)tetrahydro-2-thienyl]- and 1-[4-(hydroxymethyl)tetrahydro-3-thienyl]-thymine, -cytosine, -uracil and -fluorouracil were prepared with a chiral alpha,beta-unsaturated amide. These processes, simple in the experimental conditions and large availability of the starting materials, affording moderate to good yields of 4 '-thionucleosides, represent an optimum alternative to those, already known, based on sugars, which often have the drawbacks of a higher number of steps and lower yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.080
• 作为产物：
  描述：

  (2S,3R,4R)-2-(三甲基甲硅烷基)四氢噻吩-3,4-二羧酸二甲酯 在 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以51%的产率得到3,4-噻吩二羧酸,四氢-,二甲基酯,反-
  参考文献：
  名称：

  Aono, Masahiro; Terao, Yoshiyasu; Achiwa, Kazuo, Heterocycles, 1986, vol. 24, # 2, p. 313 - 315

  摘要：

  DOI：

文献信息

• Enzymes and catalysts. I. Pig liver esterase-catalyzed hydrolysis of heterocycli diesters.
  作者：YOSHIHISA MORIMOTO、YOSHIYASU TERAO、KAZUO ACHIWA

  DOI：10.1248/cpb.35.2266

  日期：——

  The asymmetric hydrolysis of five-membered cyclic diesters was carried out by using pig liver esterase (PLE) as a catalyst. The absolute configurations of the resulting half esters and recovered diesters were established and the stereospecificity of PLE action in such systems was revealed.

  五元环二酯的不对称水解是通过使用猪肝酯酶（PLE）作为催化剂进行的。得到的半酯和回收的二酯的绝对构型被确立，并揭示了PLE在此类体系中的立体特异性。
• Chloromethyl trimethylsilylmethyl sulphide as a parent thiocarbonyl ylide synthon. A simple synthesis of dihydro- and tetrahydro-thiophenes
  作者：Akira Hosomi、Yumiko Matsuyama、Hideki Sakurai

  DOI：10.1039/c39860001073

  日期：——

  Chloromethyl trimethylsilylmethyl sulphide acts as a parent thiocarbonyl ylide synthon and reacts stereospecifically with activated alkenes and alkynes, catalysed by caesium fluoride, in acetonitrile at room temperature to give tetrahydro- and dihydro-thiophene derivatives in good yields.

  氯甲基三甲基甲硅烷基甲基硫化物充当母体硫代羰基内酯的合成子，并在室温下在乙腈中与氟化铯催化的活化烯烃和炔烃立体定向反应，以高收率得到四氢和二氢噻吩衍生物。
• BIOTIN. V. cis-3,4-DIAMINOTHIOPHANE
  作者：B. R. BAKER、MERLE V. QUERRY、S. R. SAFIR、W. L. McEWEN、SEYMOUR BERNSTEIN

  DOI：10.1021/jo01165a022

  日期：1947.1
• BIOTIN. II. 3,4-trans-DIAMINOTHIOPHANE
  作者：GEORGE BOSWORTH BROWN、B. R. BAKER、SEYMOUR BERNSTEIN、S. R. SAFIR

  DOI：10.1021/jo01165a019

  日期：1947.1
• MORIMOTO, YOSHIHISA;TERAO, YOSHIYASU;ACHIWA, KAZUO, CHEM. AND PHARM. BULL., 35,(1987) N 6, 2266-2271
  作者：MORIMOTO, YOSHIHISA、TERAO, YOSHIYASU、ACHIWA, KAZUO

  DOI：——

  日期：——