2-(Bis-methylsulfanyl-methylene)-6-methoxy-3,4-dihydro-2H-naphthalen-1-one | 51507-10-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-(Bis-methylsulfanyl-methylene)-6-methoxy-3,4-dihydro-2H-naphthalen-1-one
• 英文别名: 2-[Bis(methylsulfanyl)methylidene]-6-methoxy-3,4-dihydronaphthalen-1-one
• CAS: 51507-10-9
• 化学式: C₁₄H₁₆O₂S₂
• 分子量: 280.412
• InChiKey: NWSFXVZMCNCWMX-UHFFFAOYSA-N

物化性质

• 沸点：
  440.1±45.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(Bis-methylsulfanyl-methylene)-6-methoxy-3,4-dihydro-2H-naphthalen-1-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-[bis(methylsulfanyl)methylidene]-6-methoxy-3,4-dihydro-1H-naphthalen-1-ol
  参考文献：
  名称：

  Polarized ketene dithioacetals. 28. A new general highly stereoselective and regiospecific method for homologation of ketones to .alpha.,.beta.-unsaturated esters via .alpha.-oxoketene dithioacetals

  摘要：

  DOI：

  10.1021/jo00174a032

文献信息

• Stepwise controlled reduction of α-Oxoketene dithioacetals with Zn/ZnCl 2 -TMEDA in ethanol
  作者：K Mallik Yadav、Joghee R Suresh、Balaram Patro、Hiriyakkanavar Ila、Hiriyakkanavar Junjappa

  DOI：10.1016/0040-4020(96)00139-1

  日期：1996.3

  α-Oxoketene dithioacetals 1 are shown to undergo highly selective conjugate reduction with Zn/ZnCl2-TMEDA in refluxing ethanol under controlled reaction conditions to afford β-methylthiomethylene ketones 6, β-methylthioketones 7 and the completely desulphurized α-methylketones 8 in sequential manner.

  在控制的反应条件下，在回流的乙醇中，α-氧杂环丁烯二硫缩醛1与Zn / ZnCl 2 -TMEDA发生高度选择性的共轭还原，依次生成β-甲基硫代亚甲基酮6，β-甲基硫代酮7和完全脱硫的α-甲基酮8。 。
• Cyclocondensation of 2-lithiomethylthiazoles and 2-lithiomethylthiazoline with α-oxoketene dithioacetals: synthesis of substituted and annelated thiazolo- and dihydrothiazolo[3,2-a]pyridinium compounds
  作者：Abraham Thomas、Hiriyakkanavar Ila、Hiriyakkanavar Junjappa

  DOI：10.1016/s0040-4020(01)86767-3

  日期：——

  The oxoketene dithioacetals 1 undergo regioselective 1,2-addition with 2-lithiomethyl-4-methylthiazole (2a) and 2-lithiomethylthiazoline (3) to afford the carbinol acetals 4 which on borontrifluoride etherate assisted cyclization yield the corresponding substituted and annelated 3-methyl-5- methylthiothiazolo[3,2-a.] pyridinium tetrafluoroborates (5a-g, 8a,b,10,12) and the dihydro derivatives (23-25)

  氧杂环丁烯二硫缩醛1与2-lithiomethyl-4-甲基噻唑（2a）和2-lithiomethylthiazoline（3）进行区域选择性1,2-加成，得到甲醇缩醛4，该缩醛4在三氟化硼醚化物协助下环化生成相应的取代和退火的3-甲基-5-甲基硫代噻唑并[3,2-a。]四氟硼酸吡啶鎓（5a-g，8a，b，10,12）和二氢衍生物（23-25）的收率很高。然而，相应的2-甲基-5-苯基噻唑（16）经历了核和侧链的去质子化，并在相似的反应条件下产生了产物的混合物。
• 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 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。
• Cyclocondensation of α-oxoketene dithioacetals with β-lithioamino-β- substituted acrylonitriles:synthesis of 2,6-substituted and 5,6-annelated 3-cyano-4- (methylthio) pyridines
  作者：Arun K. Gupta、Hiriyakkanavar Ila、Hiriyakkanavar Junjappa

  DOI：10.1016/s0040-4020(01)81540-4

  日期：1990.1

  The lithiated β-amino-β-substituted acrylonitriles 4a-d generated in situ by reaction of lithioacetonitrile with either acetonitrile or substituted nitriles undergo cyclocondensation with α-oxoketenedithioacetals through 1,4-addition to afford 2,6-substituted and 5,6-annelated-4-(methylthio)-3-cyanopyridines 6a-m, 11a-h and 12a-b in good yields. A few of the 2,6-diheterylpyridines 6n-q were also synthesized

  通过硫代乙腈与乙腈或取代的腈反应原位生成的锂化的β-氨基-β-取代的丙烯腈4a-d通过1,4-加成与α-氧杂环丁二硫缩醛进行环缩合，得到2,6-取代的和5,6-使4-（甲硫基）-3-氰基吡啶6a-m，11a-h和12a-b退火。按照该方法，还合成了一些2,6-二杂基吡啶6n-q。另一方面，将相应的α-肉桂酰基12a-c和α-（5-芳基-2,4-戊二烯酰基）（12d）酮二硫缩醛与4a环合，得到相应的4-芳基-（或4-苯乙烯基-6- [2-双（甲硫基）乙烯基] -3-氰基吡啶14a-d具有良好的产率。