1,1-bis(methylthio)-3-oxo-9-phenyl-1,4,6,8-nonatetraene | 137612-35-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,1-bis(methylthio)-3-oxo-9-phenyl-1,4,6,8-nonatetraene
• 英文别名: (4E,6E,8E)-1,1-bis(methylsulfanyl)-9-phenylnona-1,4,6,8-tetraen-3-one
• CAS: 137612-35-2
• 化学式: C₁₇H₁₈OS₂
• 分子量: 302.461
• InChiKey: SVOIVLOCHPJQKX-GKPZCNTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1-bis(methylthio)-3-oxo-9-phenyl-1,4,6,8-nonatetraene 在 锌 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 以82%的产率得到(4E,6E,8E)-1,1-bis(methylsulfanyl)-9-phenylnona-4,6,8-trien-3-one
  参考文献：
  名称：

  Rao, Ch. Srinivasa; Patro, Balaram; Ila, Hiriyakkanavar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 1, p. 57 - 59

  摘要：

  DOI：
• 作为产物：
  描述：

  4,4-bis(methylthio)but-3-en-2-one 、 (2E, 4E)-5-phenylpenta-2,4-dienal 生成 1,1-bis(methylthio)-3-oxo-9-phenyl-1,4,6,8-nonatetraene
  参考文献：
  名称：

  A FACILE SYNTHESIS OF β-OXOTHIOLCARBOXYLATES FROM α-OXOKETENEDITHIOACETALS^*

  摘要：

  alpha -Oxoketenedithioacetals and alkenoyl ketenedithioacetals underwent facile, boron trifluoride etherate assisted partial hydrolysis in dioxane to afford beta -oxothiolcarboxylates and gamma,delta -unsaturated beta -oxothiolcarboxylates, respectively, in good yields.

  DOI：

  10.1081/scc-100104056

文献信息

• Attempted Simmons-Smith reaction on α-oxoketene dithioacetals: A new general route to 3,4-substituted and annelated thiophenes
  作者：Laxminarayan Bhat、Abraham Thomas、Hiriyakkanavar Ila、Hiriyakkanavar Junjappa

  DOI：10.1016/s0040-4020(01)88342-3

  日期：1992.11

  A new general synthesis of 3- and 3,4-substituted 4a–q, 3,4-annelated 7a–d and condensed tricyclic 9a–e thiophenes has been developed through Simmons-Smith reaction on the respective α-oxoketene dithioacetals. Extension of the reaction to α-cinnamoylketene dithioacetals 10a–e and its higher enyl analogs 13a–d, 15a–c gave the corresponding 3-styryl 11a–e and 3-di- and trienyl 14a–d, 16a–c thiophenes

  通过Simmons-Smith反应在相应的α-氧杂环丁烯二硫缩醛上开发了3和3,4-取代的4a-q，3,4-退火的7a-d和稠合的三环9a-e噻吩的新的一般合成物。将反应扩展至α-肉桂酰基烯酮二硫缩醛10a-e及其高级烯基类似物13a-d，15a-c，可得到相应的3-苯乙烯基11a-e和3-二-和三烯基14a-d，16a-c噻吩区域选择性方式。已经提出了一种可能的机制，该机制涉及通过二价硫上的类胡萝卜素亚甲基插入而形成的基分子的不寻常的分子内羟醛缩合。
• Cycloaromatization of α-Oxoketene Dithioacetals with 5-Lithiomethyl-3-methylisoxazole: A New General Method for the Synthesis of Substituted and Annulated 1,2-Benzisoxazoles
  作者：Dinah Pooranchand、J. Satyanarayana、H. Ila、H. Junjappa

  DOI：10.1055/s-1993-25840

  日期：——

  A new route to 6-substituted 4a-e and 5,6-annulated 4f-l 1,2-benzisoxazoles has been developed through regioselective 1,2-nucleophilic addition of 5-lithiomethyl-3-methylisoxazole (2) to a variety of α-oxoketene dithioacetals 1a-l and subsequent cycloaromatization of the resulting hydroxyacetals in the presence of boron trifluoride -diethyl ether complex. The corresponding 4-dethiomethylated benzisoxazoles 6a-d were also synthesized by cyclocondensation of β- methylthio-α,β-unsaturated ketones with 2 under identical conditions. The reaction was further extended for the synthesis of (6-benzisoxazolyl)-substituted ethylenes 9a-e, butadienes 9f-g and hexatriene 9h by subjecting α-cinnamoyl ketene dithioacetals 7a-e and their higher enyl analogs 7f-h to similar transformations.

  通过将 5-硫代甲基-3-甲基异噁唑（2）与多种δ-±-氧代酮二硫代乙醛 1a-l 进行 1,2-亲核加成，并随后在三氟化硼-二乙基醚络合物存在下对所生成的羟基乙醛进行环芳基化，开发出了一条制备 6-取代型 4a-e 和 5,6-annulated 4f-l 1,2-苯并异噁唑的新途径。在相同的条件下，δ-甲硫基-δ,δ-不饱和酮与 2 环缩合，也合成了相应的 4-二硫甲基化苯并异噁唑 6a-d。通过使δ-肉桂酰基酮二硫代乙醛 7a-e 及其高烯基类似物 7f-h 发生类似的转化，该反应进一步扩展到合成（6-苯并异噁唑基）取代的乙烯 9a-e、丁二烯 9f-g 和己三烯 9h。
• Darzen's reaction on oxoketene dithioacetals: A new versatile synthesis of substituted and annelated furan-2-carboxylates
  作者：Apurba Datta、Dinah Pooranchand、Hiriyakkanavar Ila、Hiriyakkanavar Junjappa

  DOI：10.1016/s0040-4020(01)89224-3

  日期：1989.1
• Purkayastha, M. L.; Patro, B.; Ila, H., Journal of Heterocyclic Chemistry, 1991, vol. 28, # 5, p. 1341 - 1350
  作者：Purkayastha, M. L.、Patro, B.、Ila, H.、Junjappa, H.

  DOI：——

  日期：——
• A FACILE SYNTHESIS OF β-OXOTHIOLCARBOXYLATES FROM α-OXOKETENEDITHIOACETALS^*
  作者：Satheesh K. Nair、C. V. Asokan

  DOI：10.1081/scc-100104056

  日期：2001.1

  alpha -Oxoketenedithioacetals and alkenoyl ketenedithioacetals underwent facile, boron trifluoride etherate assisted partial hydrolysis in dioxane to afford beta -oxothiolcarboxylates and gamma,delta -unsaturated beta -oxothiolcarboxylates, respectively, in good yields.