4a-methyl-4,4a,7,8-tetrahydro-3H-spiro[naphthalene-2,2'-[1,3]dithian]-5(6H)-one | 134836-77-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 4a-methyl-4,4a,7,8-tetrahydro-3H-spiro[naphthalene-2,2'-[1,3]dithian]-5(6H)-one
• 英文别名: 8'a-methylspiro[1,3-dithiane-2,6'-3,4,7,8-tetrahydro-2H-naphthalene]-1'-one
• CAS: 134836-77-4
• 化学式: C₁₄H₂₀OS₂
• 分子量: 268.444
• InChiKey: OGBMEMLVUANHNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  苯肼,盐酸盐 、 4a-methyl-4,4a,7,8-tetrahydro-3H-spiro[naphthalene-2,2'-[1,3]dithian]-5(6H)-one 在 溶剂黄146 作用下， 反应 2.0h， 以41%的产率得到11b-methyl-1,2,5,6,11,11b-hexahydrospiro[benzo[a]carbazole-3,2'-[1,3]dithiane]
  参考文献：
  名称：

  A synthetic approach to (±)-aristomakine

  摘要：

  We describe the synthesis of trans-11b-methyl-2,3,4,6,11,11b-hexahydro-1H-benzo[a]carbazol-3-ol (2) in five steps from the Wieland-Miescher ketone 3 in 17% overall yield. The N-benzyl analogue (trans-11-Benzyl-11b-methyl-2,3,4,6,11,11b-hexahydro-1H-benzo[a]carbazol-3-ol) 15 was likewise prepared. Attempts thus far to fashion (+/-)-aristomakine (1) from 2, 15, or derivatives have not been successful.[GRAPHICS].

  DOI：

  10.24820/ark.5550190.p010.543
• 作为产物：
  描述：

  2-甲基-1,3-环己二酮 在 三氟化硼乙醚 、 potassium hydroxide 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 3.0h， 生成 4a-methyl-4,4a,7,8-tetrahydro-3H-spiro[naphthalene-2,2'-[1,3]dithian]-5(6H)-one
  参考文献：
  名称：

  A synthetic approach to (±)-aristomakine

  摘要：

  We describe the synthesis of trans-11b-methyl-2,3,4,6,11,11b-hexahydro-1H-benzo[a]carbazol-3-ol (2) in five steps from the Wieland-Miescher ketone 3 in 17% overall yield. The N-benzyl analogue (trans-11-Benzyl-11b-methyl-2,3,4,6,11,11b-hexahydro-1H-benzo[a]carbazol-3-ol) 15 was likewise prepared. Attempts thus far to fashion (+/-)-aristomakine (1) from 2, 15, or derivatives have not been successful.[GRAPHICS].

  DOI：

  10.24820/ark.5550190.p010.543

文献信息

• Tellurium tetrachloride as a mild and efficient catalyst for dithioacetalization
  作者：Hiroyuki Tani、Kazunori Masumoto、Tokuo Inamasu、Hitomi Suzuki

  DOI：10.1016/s0040-4039(00)78902-7

  日期：1991.4

  A variety of aldehydes and aliphatic ketones were converted into the corresponding dithioacetals at room temperature in good yields by using small amounts of tellurium tetrachloride as a mild Lewis acid catalyst.

  通过使用少量的四氯化碲作为温和的路易斯酸催化剂，多种醛和脂肪族酮在室温下以良好的产率转化为相应的二硫缩醛。
• A synthetic approach to (±)-aristomakine
  作者：Robert B. Perni、Gordon W. Gribble

  DOI：10.24820/ark.5550190.p010.543

  日期：——

  We describe the synthesis of trans-11b-methyl-2,3,4,6,11,11b-hexahydro-1H-benzo[a]carbazol-3-ol (2) in five steps from the Wieland-Miescher ketone 3 in 17% overall yield. The N-benzyl analogue (trans-11-Benzyl-11b-methyl-2,3,4,6,11,11b-hexahydro-1H-benzo[a]carbazol-3-ol) 15 was likewise prepared. Attempts thus far to fashion (+/-)-aristomakine (1) from 2, 15, or derivatives have not been successful.[GRAPHICS].