8,9-dimethoxy-10b-methyl-6,10b-dihydro-5H-thiazolo[2,3-a]isoquinoline-3-one | 18332-20-2

• 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: 8,9-dimethoxy-10b-methyl-6,10b-dihydro-5H-thiazolo[2,3-a]isoquinoline-3-one
• 英文别名: 8,9-dimethoxy-10b-methyl-6,10b-dihydro-5H-thiazolo[2,3-a]isoquinolin-3-one；8,9-dimethoxy-6,10b-dihydro-5H-thiazolo[2,3-a]isoquinolin-3-one；8,9-dimethoxy-10b-methyl-6,10b-dihydro-5H-[1,3]thiazolo[2,3-a]isoquinolin-3(2H)-one；8,9-dimethoxy-10b-methyl-5,6-dihydro-[1,3]thiazolo[2,3-a]isoquinolin-3-one
• CAS: 18332-20-2
• 化学式: C₁₄H₁₇NO₃S
• 分子量: 279.36
• InChiKey: FCZXUSJRKYUTOB-UHFFFAOYSA-N

物化性质

• 熔点：
  129-130 °C
• 沸点：
  458.6±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  8,9-dimethoxy-10b-methyl-6,10b-dihydro-5H-thiazolo[2,3-a]isoquinoline-3-one 在 sodium hydroxide 、 Raney nickel W-4 、 双氧水 作用下， 以 甲醇 、 乙醇 、 氯仿 、 水 为溶剂， 反应 123.25h， 生成 6,7-二甲氧基-1-甲基-1,2,3,4-四氢异喹啉
  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：

  溴乙酰氯 、 N-thioacetyl-β-(3,4-dimethoxyphenyl)-ethylamine 生成 8,9-dimethoxy-10b-methyl-6,10b-dihydro-5H-thiazolo[2,3-a]isoquinoline-3-one
  参考文献：
  名称：

  π-Cyclization reactions of thio N-acyliminium ions for heterocyclic synthesis

  摘要：

  Thio N-acyliminium ions are readily generated from the reaction of thioamides with bromoacetyl chloride. In the presence of tethered pi-nucleophiles, cyclization occurs to give S,N-acetals which can be further converted into various alkaloid skeletons. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00902-2

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）。
• Ritter Reactions. XIII Reactivity of Methyl Schiff Bases with Dimethyl Acetylenedicarboxylate and Mercaptoacetic Acid
  作者：Qinghong Lin、Djamal Djaidi、Roger Bishop、Donald C. Craig、Marcia L. Scudder

  DOI：10.1071/c98025

  日期：——

  Reactions of several methyl imines with dimethyl acetylenedicarboxylate and with mercaptoacetic acid have been studied to investigate further the capricious behaviour of this functionality. The 1 : 1 adduct of imine (1) and dimethyl acetylenedicarboxylate is confirmed as the pyrroloisoquinoline structure (7) by X-ray methods [C17H17NO5, P -1, a 9·037(2), b 9·276(2), c 10·033(2) Å, α 81·99(1), β 81·28(1), γ 64·9(2)°, Z 2, R 0·044]. New products from (2) and dimethyl acetylenedicarboxylate, the 1 : 1 adduct (10) which is readily converted into the known product (9), and the 1 : 2 adduct (12), are described. The structure of the last compound, which arises through a rearrangement process, was determined by X-ray crystallography [C27H36N2O9,P ca21, a 19· 083(4), b 15·217(3), c 9·669(2) Å, Z 4, R 0·038]. Methyl imines (1) and (4) undergo cyclocondensation with mercaptoacetic acid yielding thiazolidinone products but others are inert under similar conditions.

  研究了几种甲基亚胺与乙炔二甲酸二甲酯以及与巯基乙酸的反应。 与巯基乙酸的反应进行了研究，以进一步探讨这种官能团的任性行为。 这种官能团的多变行为。亚胺 (1) 与乙炔二甲酸二甲酯的 1 : 1 加合物 乙炔二甲酸二甲酯的 1 : 1 加合物被 X 射线方法证实为吡咯异喹啉结构 (7)。 结构 (7) [C17H17NO5、 P -1, a 9-037(2), b 9-276(2), c 10-033(2) Å, α 81-99(1)、 β 81-28(1)，γ 64-9(2)°，Z 2、 R 0-044].由 (2) 和乙炔二甲酸二甲酯生成的新产品 乙炔二甲酸二甲酯的新产物，1:1 加合物 (10) 很容易转化为已知产物 (9)。 加合物 (10) 很容易转化为已知产品 (9)，以及 1 : 2 加合物 (12)。最后一种化合物的结构 最后一种化合物是通过重排过程产生的，其结构是通过 X 射线晶体学测定的。 通过 X 射线晶体学测定 [C27H36N2O9,P ca21、 a 19- 083(4), b 15-217(3), c 9-669(2) Å、 Z 4，R 0-038]。甲基 亚胺 (1) 和 (4) 会与巯基乙酸发生环缩合反应，生成 噻唑烷酮产品，但其他产品在类似条件下是惰性的。
• A One-Pot Bicycloannulation Method for the Synthesis of Tetrahydroisoquinoline Systems
  作者：Albert Padwa、L. Scott Beall、Todd M. Heidelbaugh、Bing Liu、Scott M. Sheehan

  DOI：10.1021/jo991742h

  日期：2000.5.1

  A highly effective method for the synthesis of the core indolo[2,3-a]quinolizidine skeleton found in yohimbine is described. The reaction of N-monosubstituted thioamides with bromoalkenoyl chlorides furnishes thioisomunchnones as transient 1,3-dipoles that undergo ready intramolecular cycloaddition across the tethered pi-bond to give thio-bicycloannulated products in a one-pot operation. The stereochemical outcome of the intramolecular reaction is the consequence of an endo cycloaddition of the neighboring-bond across the transient thioisomunchnone dipole. A major limitation of the method is that when a hydrogen is present in the alpha-position of the thioamide the initially formed thio-N-acyliminium ion undergoes proton loss to produce a S ,N-ketene acetal at a faster rate than dipole formation. Treatment of tetrahydro-beta-carboline-1-thione with 2-bromooct-7-enoyl chloride followed by reductive removal of sulfur from the cycloadduct resulted in the formation of (+/-)-alloyahimbanone. Attempts to cycloadd the thioisomunchnone dipole across several nucleophilic-bonds failed, and instead, products derived from cyclization of the pi-bond onto the initially formed thio-N-acyliminium ion were formed. The resulting N,S-ketals were further converted into several tetrahydroisoquinoline alkaloids in good yield.
• Nair,M.D. et al., Indian Journal of Chemistry, 1967, vol. 5, p. 221 - 223
  作者：Nair,M.D. et al.

  DOI：——

  日期：——
• 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).