5-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-2,2-dimethyl-1,3-dioxanee-4,6-dione | 200711-28-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-2,2-dimethyl-1,3-dioxanee-4,6-dione
• 英文别名: 5-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione；5-(4-Chloro-5h-1,2,3-dithiazol-5-ylidene)-2,2-dimethyl-1,3-dioxan-4,6-dione；5-(4-chlorodithiazol-5-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 200711-28-0
• 化学式: C₈H₆ClNO₄S₂
• 分子量: 279.725
• InChiKey: VNIACESUVYYIDB-UHFFFAOYSA-N

物化性质

• 沸点：
  422.4±55.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  苯胺 、 5-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-2,2-dimethyl-1,3-dioxanee-4,6-dione 以 二氯甲烷 为溶剂， 反应 40.0h， 以91%的产率得到5-[(phenylamino)(cyano)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  A facile synthesis of 5-[(arylamino)(cyano)methylene]-2,2-dimethyl-1,3-dioxane-4,6-diones

  摘要：

  Treatment of 5-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-2,2-dimethyl- 1,3-dioxane-4,6-dione with primary arylamines in CH2Cl2 at rt gave 5-[(arylamino)(cyano)methylene]-2,2-dimethyl-1,3-dioxane-4,6-diones in excellent yields. The latter compounds were utilized for the preparation of 2-cyano-4-quinolinones. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00073-3
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 4,5-二氯-1,2,3-二噻唑氯化物 在 2,6-二甲基吡啶 作用下， 以87%的产率得到5-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-2,2-dimethyl-1,3-dioxanee-4,6-dione
  参考文献：
  名称：

  D'hooge, Bart; Dehaen, Wim, Bulletin des Societes Chimiques Belges, 1997, vol. 106, # 11, p. 729 - 730

  摘要：

  DOI：

文献信息

• Reactions of 5-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione with primary and secondary alkylamines †
  作者：Moon-Kook Jeon、Kyongtae Kim

  DOI：10.1039/b003109g

  日期：——

  The reactions of 5-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione with primary alkylamines (2 equiv.) in CH2Cl2 at rt gave 5-[(alkylamino)(cyano)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-diones (2) in excellent yields. Similarly, the reactions with ethylenediamine, trans-1,2-diaminocyclohexane, 2-aminobenzylamine, and 2-aminoethanol under the same conditions afforded 5-(imidazolidin-2-ylidene)- (3a), 5-(octahydro-2H-benzimidazol-2-ylidene)- (3b), 5-[3,4-dihydroquinazolin-2(1H)-ylidene]- (3c), and 5-(1,3-oxazolidin-2-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-diones (3d) in moderate to excellent yields. Interestingly, the reactions with secondary acyclic dialkylamines under the same conditions yielded 5-(4-dialkylamino-5H-1,2,3-dithiazol-5-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-diones (7) (0–60%), 6-carbamoyl-5-oxo-5H-furo[2,3-d][1,2,3]-dithiazoles (8) (0–28%), sulfur, and bis(dialkylamino) sulfides (R2N–Sx–NR2), whereas the reactions with cyclic amines, i.e., pyrrolidine and piperidine, gave the corresponding methylidene-Meldrums acid derivatives 9, analogous to 2, as major products. Mechanisms are proposed for the formation of these products.

  盐酸盐（1）和甲基烯丙基-Meldrums盐酸盐（2）。
• Emayan, Kumaraswamy; English, Russell F.; Koutentis, Panayiotis A., Journal of the Chemical Society. Perkin transactions I, 1997, # 22, p. 3345 - 3349
  作者：Emayan, Kumaraswamy、English, Russell F.、Koutentis, Panayiotis A.、Rees, Charles W.

  DOI：——

  日期：——
• D'hooge, Bart; Dehaen, Wim, Bulletin des Societes Chimiques Belges, 1997, vol. 106, # 11, p. 729 - 730
  作者：D'hooge, Bart、Dehaen, Wim

  DOI：——

  日期：——
• A facile synthesis of 5-[(arylamino)(cyano)methylene]-2,2-dimethyl-1,3-dioxane-4,6-diones
  作者：Moon-Kook Jeon、Kyongtae Kim

  DOI：10.1016/s0040-4039(00)00073-3

  日期：2000.3

  Treatment of 5-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-2,2-dimethyl- 1,3-dioxane-4,6-dione with primary arylamines in CH2Cl2 at rt gave 5-[(arylamino)(cyano)methylene]-2,2-dimethyl-1,3-dioxane-4,6-diones in excellent yields. The latter compounds were utilized for the preparation of 2-cyano-4-quinolinones. (C) 2000 Elsevier Science Ltd. All rights reserved.