7,8-dimethoxy-3-oxo-3a,4,5,9b-tetrahydroisoquinolino<1,2-b>thiazolidine | 13363-67-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 7,8-dimethoxy-3-oxo-3a,4,5,9b-tetrahydroisoquinolino<1,2-b>thiazolidine
• 英文别名: 8,9-dimethoxy-2,5,6,10b-tetrahydrothiazolo<2,3-a>isoquinolin-3-one；8,9-dimethoxy-6,10b-dihydro-5H-thiazolo[2,3-a]isoquinolin-3-one；8,9-dimethoxy-6,9b-dihydro-5H-thiazolo[2,3-a]isoqinolin-3-one；8,9-dimethoxy-6,10b-dihydro-5H-thiazolo[2,3-a]isoquinolin-3-one；8,9-dimethoxy-6,10b-dihydro-5H-[1,3]thiazolo[2,3-a]isoquinolin-3-one
• CAS: 13363-67-2
• 化学式: C₁₃H₁₅NO₃S
• 分子量: 265.333
• InChiKey: RLRKJEUXXGPDQH-UHFFFAOYSA-N

物化性质

• 熔点：
  176 °C
• 沸点：
  465.9±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  64.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7,8-dimethoxy-3-oxo-3a,4,5,9b-tetrahydroisoquinolino<1,2-b>thiazolidine 在 双氧水 、 sodium hydride 作用下， 以 甲醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 8,9-dimethoxy-2-methyl-1-oxo-6,10b-dihydro-5H-thiazolo[2,3-a]isoquinolin-3-one
  参考文献：
  名称：

  Rozwadowska; Sulima, Polish Journal of Chemistry, 2001, vol. 75, # 12, p. 1847 - 1852

  摘要：

  DOI：
• 作为产物：
  描述：

  9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizin-2-one 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 18.0h， 生成 7,8-dimethoxy-3-oxo-3a,4,5,9b-tetrahydroisoquinolino<1,2-b>thiazolidine
  参考文献：
  名称：

  Menendez, J. Carlos; Soellhuber, Monica M., Heterocycles, 1990, vol. 31, # 11, p. 2065 - 2071

  摘要：

  DOI：

文献信息

• Synthesis and spectroscopic studies of some hydrogenated thiazolo[2,3- a ]isoquinolines
  作者：Maria D Rozwadowska、Agnieszka Sulima

  DOI：10.1016/s0040-4020(01)00224-1

  日期：2001.4

  4-dihydroisoquinoline derivatives under the action of α-mercapto alkanoic acids or ethylene sulfide, respectively. In the synthesis of compounds 2 and 5 isothiocarbostril (13) and N-thioacetyl-β-phenylethylamine derivatives (14), respectively, were also used as substrates and treated with bromoacetic acid derivatives. Spectral characteristics (IR, 1H, 13C NMR and MS) of compounds 1–12 are presented.

  二氢-5- ħ -噻唑并[2,3-一个]异喹啉酮（1 - 6）和四氢-5- ħ -噻唑并[2,3一]异喹啉（7 - 12）已经从下3,4-二氢异喹啉衍生物制备α-巯基链烷酸或亚乙基硫的作用。在化合物2和5的合成中，异硫脲化合物（13）和N-硫代乙酰基-β-苯乙胺衍生物（14）也分别用作底物，并用溴乙酸衍生物处理。光谱特性（IR，1 H，给出了化合物1 – 12的13 C NMR和MS）。
• Schneider,W.; Kaemmerer,E., Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, 1966, vol. 299, p. 846 - 857
  作者：Schneider,W.、Kaemmerer,E.

  DOI：——

  日期：——
• Synthesis, crystal structure and oxidation of (R)-(+)-8,9-dimethoxy-6,10b-dihydro-5H-thiazolo[2,3-a]isoquinolin-3-one
  作者：M.D. Rozwadowska、A. Sulima、A. Gzella

  DOI：10.1016/s0957-4166(02)00633-x

  日期：2002.10

  (R)-(+)-8,9-Dimethoxy-6,10b-dihydro-5H-thiazolo[2,3-a]isoquinolin-3-one 1 has been synthesized from 6,7-dimethoxy-3,4-dihydroisoquinoline and menthyl thioglycolate. Compound 1 was obtained in the enantiomerically pure form (mp 150-153degreesC, [alpha](D) +436) by a single crystallization of the crude reaction product (68% e.e.) from 96% ethanol. The absolute 10bR configuration was established by X-ray diffraction. Oxone oxidation of 1 resulted in a configurationally unstable dextrorotatory syn-sulfoxide 2 (mp 173-175degreesC, [alpha](D) +62.8). (C) 2002 Elsevier Science Ltd. All rights reserved.
• Studies of some hydrogenated thiazolo[2,3-a]isoquinoline S-oxides
  作者：M.D Rozwadowska、A Sulima

  DOI：10.1016/s0040-4020(03)00023-1

  日期：2003.2

  Several hydrogenated thiazolo[2,3-a]isoquinolinone S-oxides have been prepared and their stereochemistry established on the basis of spectral data analysis combined with X-ray crystallography. A reversible syn/anti isomerization of diastereomeric sulfoxides has been postulated to occur via a 10b proton abstraction. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Two thiazolino[2,3-<i>a</i>]isoquinolinone<i>S</i>-oxides
  作者：Andrzej Gzella、Maria D. Rozwadowska、Agnieszka Sulima

  DOI：10.1107/s0108270101016638

  日期：2001.12.15

  The structures of two racemic thiazolino[2,3-a]isoquinolinone S-oxides, i.e. 8,9-dimethoxy-2,3,5,6-tetrahydro-10bH-thiazolo[2,3-a]isoquinolin-3-one 1-oxide [C13H15NO4S, (IIa)] and 8,9-dimethoxy-10b-methyl-2,3,5,6-tetrahydro-10bH-thiazolo- [2,3-a]isoquinolin-3-one 1-oxide [C14H17NO4S, (IIb)], are described. The thiazolinone ring in (IIa) exists in an envelope conformation, while in (IIb), it assumes a half-chair conformation. In (IIa) and (IIb), the six-membered heterocyclic ring adopts an envelope conformation. The O atom at sulfur is oriented in a pseudo-axial position, whereas the H atom in (IIa) and the methyl group in (IIb), linked to the stereogenic C centre, occupy a bisectional position with respect to the partially saturated pyridine ring and a pseudo-axial position with respect to the thiazolinone ring. In both structures, the S=O group and the substituent at the stereogenic C centre are trans with respect to one another. Intermolecular C-H . . .O hydrogen bonds are observed in the crystal lattice of (IIa) and (IIb).