3-thiophthalimide-2,4-pentanedione | 107552-89-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-thiophthalimide-2,4-pentanedione
• 英文别名: 1H-Isoindole-1,3(2H)-dione, 2-[(1-acetyl-2-oxopropyl)thio]-；2-(2,4-dioxopentan-3-ylsulfanyl)isoindole-1,3-dione
• CAS: 107552-89-6
• 化学式: C₁₃H₁₁NO₄S
• 分子量: 277.301
• InChiKey: YTUQAKQNUXTCOX-UHFFFAOYSA-N

物化性质

• 熔点：
  140 °C (decomp)
• 沸点：
  428.6±55.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  96.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-thiophthalimide-2,4-pentanedione 在 三氟甲磺酸三甲基硅酯 作用下， 以 吡啶 、 二氯甲烷 、 氯仿 为溶剂， 反应 98.0h， 生成 2,3,4-tri-O-benzyl-6-acetyl-1-deoxy-D-glucopyranose-1-spiro-6'-[1'-(5'H-2'-methyl-1',4'-oxathiin-3'-yl)ethanone]
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of 4‘-Thiaspiroacetals from Carbohydrates

  摘要：

  DOI：

  10.1021/jo990416z
• 作为产物：
  描述：

  phthalimidesulfenyl chloride 、 乙酰丙酮 反应 0.25h， 以88%的产率得到3-thiophthalimide-2,4-pentanedione
  参考文献：
  名称：

  Mullin, V. A.; Zolotov, A. N., Journal of general chemistry of the USSR, 1986, vol. 56, p. 791 - 796

  摘要：

  DOI：

文献信息

• Thiaspiroacetals from Carbohydrates
  作者：Giuseppe Capozzi、Alessandra Bartolozzi、Chiara Falciani、Stefano Menichetti、Cristina Nativi

  DOI：10.1080/10426509908546445

  日期：1999.1

  The inverse electron demand [4+2] cycloaddition between glycoexoenitols and α,α'-dioxothiones or ortho-thioquinones represents a selective way to achieve 4'-thiaspiroacetals, an unusual class of spiroderivatives, from carbohydrate.

  糖外烯醇和 α,α'-二氧硫酮或邻硫醌之间的逆电子需求 [4+2] 环加成代表了一种从碳水化合物中获得 4'-硫杂螺缩醛（一种不寻常的螺旋衍生物）的选择性方法。
• Recent advances in the synthesis of 2-deoxy-glycosides
  作者：Dianjie Hou、Todd L. Lowary

  DOI：10.1016/j.carres.2009.07.013

  日期：2009.10

  Glycosides of 2-deoxy-sugars, monosaccharides in which the hydroxyl group at C-2 is replaced with a hydrogen atom, occur widely in natural products and therefore have been the subject of intense synthetic activity. The report summarizes recent advances in this area, with a particular focus on work published since an earlier review on the topic, in 2000 (Marzabadi, C. H.: Franck, R. W. Tetrahedron 2000, 56, 8385-8417). (C) 2009 Elsevier Ltd. All rights reserved.
• Novel Bicylic Donors for the Synthesis of 2-Deoxy-β-Glycosides
  作者：Richard W. Franck、Cecilia H. Marzabadi

  DOI：10.1021/jo971934h

  日期：1998.4.1

  Novel bicyclic glycosyl donors have been prepared by the cycloaddition reaction of glycals with 3-thiono-2,4-pentanedione 17 followed by methylenation of the resulting ketone. Treatment of the heterocyclic donors with triflic acid in the presence of a variety of alcohol accepters leads to the formation of beta-glycosides in good yields and with excellent stereoselectivities. Desulfurization of the C-2 carbon-sulfur bonds gives the corresponding 2-deoxy-beta-glycosides. This method has been extended to the synthesis of glycosidic linkages found in the aureolic acid antibiotics. Tetra-N-butylammonium triflate proved to be a useful additive in these glycosylation reactions, suggesting an important role for triflate anion in stabilizing intermediates which are formed.
• Conformational evaluation of some 4-deoxyhex-4-enopyranose derivatives and their use in the preparation of a previously undescribed class of 3-thio-l-sorbopyranosides and their 6-C-methoxy analogues
  作者：Giuseppe Capozzi、Giorgio Catelani、Felicia D'Andrea、Stefano Menichetti、Cristina Nativi

  DOI：10.1016/s0008-6215(02)00431-7

  日期：2003.1

  A new series of thio-substituted sugars were synthesised relying on the totally regio- and stereoselective cycloaddition of 4-deoxyhex-4-enopyranose derivatives to 'in situ' generated oxothiones. Conformational studies of the above unsaturated sugars showed a marked prevalence of the all-axial conformer. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Capozzi, Giuseppe; Dios, Angeles; Franck, Richard W., Angewandte Chemie, 1996, vol. 108, # 7, p. 805 - 807
  作者：Capozzi, Giuseppe、Dios, Angeles、Franck, Richard W.、Geer, Aloma、Marzabadi, Cecilia、et al.

  DOI：——

  日期：——