2-(bis-methylsulfanyl-methylene)-indan-1-one | 61402-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(bis-methylsulfanyl-methylene)-indan-1-one
• 英文别名: 1H-Inden-1-one, 2-[bis(methylthio)methylene]-2,3-dihydro-；2-[bis(methylsulfanyl)methylidene]-3H-inden-1-one
• CAS: 61402-25-3
• 化学式: C₁₂H₁₂OS₂
• 分子量: 236.359
• InChiKey: CTDVSUGJQHQLOL-UHFFFAOYSA-N

物化性质

• 熔点：
  124-125 °C(Solv: methanol (67-56-1))
• 沸点：
  378.6±42.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2-(bis-methylsulfanyl-methylene)-indan-1-one 在 三氟化硼乙醚 作用下， 以 乙醚 、 苯 为溶剂， 反应 12.75h， 生成 3-methylindene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Singh, Gurdeep; Purkayastha, Makhan L.; Ila, Hiriyakkanavar, Journal of the Chemical Society. Perkin transactions I, 1985, p. 1289 - 1294

  摘要：

  DOI：
• 作为产物：
  描述：

  2-[(Methylsulfanyl)(sulfanyl)methylidene]-2,3-dihydro-1H-inden-1-one 、 重氮甲烷 生成 2-(bis-methylsulfanyl-methylene)-indan-1-one
  参考文献：
  名称：

  VARECH D.; JACQUES J.; PLATZER N.; BASSELIER J.-J., BULL. SOC. CHIM. FRANCE , 1976, NO 7-8, PART. 2, 1255-1256, 15

  摘要：

  DOI：

文献信息

• A Convenient One-Pot Synthesis of Ketene Dithioacetals
  作者：Didier Villemin、Abdelkrim Ben Alloum

  DOI：10.1055/s-1991-26449

  日期：——

  An easy synthesis of ketene dithioacetals 2 and 3 by the condensation of carbon disulfide and active methylene compounds 1 with subsequent alkylation in the presence of potassium fluoride is described.

  报道了通过二硫化碳与活性甲基酮化合物1的缩合反应，随后在氟化钾存在下进行烷基化，简便合成乙烯酮二硫代乙缩醛2和3的方法。
• Cycloaromatization of α-oxoketene dithioacetals and β-oxodithioacetals with benzyl-,1-(naphthylmethyl) and 2-(naphthylmethyl)magnesium halides: Synthesis of condensed polynuclear aromatic hydrocarbons
  作者：Ch.Srinivasa Rao、Maliakel P Balu、Hiriyakkanavar Ila、Hiriyakkanavar Junjappa

  DOI：10.1016/s0040-4020(01)86411-5

  日期：1991.1

  An efficient route for the synthesis of substituted naphthalenes, phenanthrenes and other polynuclear aromatic hydrocarbons has been developed. The methodology involves 1,2- (or sequential 1,4- and 1,2-) addition of either benzyl, 1-(naphthylmethyl) or 2-(naphthylmethyl) magnesium halides to α-oxoketene dithioacetals or β-oxodithioacetals followed by borontrifluoride etherate catalyzed cycloaromatization

  已经开发了合成取代的萘，菲和其他多核芳烃的有效途径。该方法包括在α-氧杂环丁烯二硫缩醛或β-氧二硫缩醛中加入苄基，1-（萘基甲基）或2-（萘基甲基）卤化镁的1,2-（或顺序的1,4-和1,2-），然后再加入三氟化硼醚化物催化所得甲醇的环芳构化。
• α-Oxoketene Dithioacetals Mediated Benzoannelation of Aromatic Heterocycles: an Efficient Regiocontrolled Synthesis of Highly Substituted and Polycyclic Benzo[b]thiophenes
  作者：J.R. Suresh、Okram Barun、H. Ila、H. Junjappa

  DOI：10.1016/s0040-4020(00)00722-5

  日期：2000.10

  An efficient regiocontrolled synthesis of highly substituted and complex polycyclic benzo[b]thiophenes has been developed via our benzoannelation strategy involving conjugate addition–displacement on a variety of α-oxoketene dithioacetals by carbanions derived from 2- and 3-cyanomethylthiophenes followed by acid induced cyclization of the resulting conjugate adducts.

  通过我们的苯甲酰化策略，开发了一种高效的区域控制的合成方法，该方法可控制区域取代基和复杂的多环苯并[ b ]噻吩，包括通过2-和3-氰基甲基噻吩的碳负离子在各种α-氧杂环丁烯二硫缩醛上进行共轭加成-置换，然后进行酸诱导的环化反应生成的共轭加合物。
• α-Oxoketene dithioacetal mediated aromatic annulation: highly efficient and concise synthetic routes to potentially carcinogenic polycyclic aromatic hydrocarbons
  作者：Sukumar Nandi、Kausik Panda、J.R Suresh、Hiriyakkanavar Ila、Hiriyakkanavar Junjappa

  DOI：10.1016/j.tet.2004.02.053

  日期：2004.4

  Highly efficient regiospecific routes to potentially carcinogenic polycyclic aromatic hydrocarbons such as substituted benzo[c]phenanthrenes, benzo[c]fluorenes, 16,17-dihydro-11-methyl-15[H]cyclopenta[a]phenanthrene, 5-methyl-7,8,9,10-tetrahydrochrysene and 1,4-dimethylphenanthrene have been developed. The overall strategy involves our aromatic annulation protocol through base induced conjugate addition–elimination

  高效的区域特异性途径转化为潜在的致癌多环芳烃，例如取代的苯并[ c ]菲，苯并[ c ]芴，16,17-二氢-11-甲基-15 [ H ]环戊[ a ]菲，5-甲基-7已经开发了8，9，10-四氢丙烯和1，4-二甲基菲。总体策略涉及我们的芳族环化方案，即通过碱诱导的共轭加成反应-在环和无环α-氧杂环丁烯二硫缩醛上用适当的芳基乙腈消除，然后酸诱导所得的共轭加合物进行环脱水。随后环化产物的还原性脱硫甲基化（阮内镍）和脱氢（DDQ）以高收率提供了甲基取代的PAH。
• Regio- and chemoselective conjugate 1,4-reduction of α-oxoketene dithioacetals with sodium borohydride and sodium cyanoborohydride
  作者：Ch. Srinivasa Rao、R.T. Chakrasali、Hiriyakkanavar Ila、Hiriyakkanavar Junjappa

  DOI：10.1016/s0040-4020(01)89784-2

  日期：1990.1

  Theα-oxoketene dithioacetals are shown to undergo conjugate 1,4-reduction in highly regio- and chemoselective manner with sodium borohydride in acetic acid to afford the corresponding β-oxodithioacetals in good yields. These results have been rationalized according to HSAB principle in terms of 'hard soft affinity inversion' concept. The reduction of with sodium cyanoborohydride also proceeds in 1

  已显示α-氧杂环丁烯二硫缩醛与乙酸中的硼氢化钠以高度区域选择性和化学选择性的方式进行共轭1,4-还原，从而以良好的收率得到相应的β-氧二硫缩醛。根据“硬软亲和力反演”概念，根据HSAB原理对这些结果进行了合理化。用氰基硼氢化钠还原也以1，4-共轭加成-消除的方式进行，以良好的收率得到相应的乙烯基硫醇酯。