(8-oxo-1,4-dioxaspiro[4.5]decan-7-yl) N,N-dimethylcarbamodithioate | 1385024-85-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (8-oxo-1,4-dioxaspiro[4.5]decan-7-yl) N,N-dimethylcarbamodithioate
• CAS: 1385024-85-0
• 化学式: C₁₁H₁₇NO₃S₂
• 分子量: 275.393
• InChiKey: YVMAWYJLKRCWFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  96.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (8-oxo-1,4-dioxaspiro[4.5]decan-7-yl) N,N-dimethylcarbamodithioate 在 lithium aluminium tetrahydride 、 盐酸 作用下， 以 四氢呋喃 、 乙醚 、 水 、 乙酸乙酯 为溶剂， 反应 16.0h， 以87%的产率得到C₁₁H₁₉NO₃S₂
  参考文献：
  名称：

  TBD-catalyzed α-sulfenylation of cyclic ketones: desymmetrization of 4-substituted cyclohexanones

  摘要：

  A low loading of triazabicyclo[4.4.0]dec-5-ene (TBD) catalyzes the alpha-sulfenylation reaction of ketones employing tetramethylthiuram disulfide (TMTDS) as electrophilic reagent. This methodology is mild, effective and straightforward, rendering the desired products in high yield. Prochiral 4-substituted cyclohexanones can be desymmetrized with remarkable diastereoselectivity following this protocol. The dithiocarbamoyl function was shown to be easily removed upon reduction, affording thiols (1-mercaptan-2-ols). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.124
• 作为产物：
  描述：

  1,4-环己二酮单乙二醇缩酮 、 福美双 在 1,5,7-三氮杂双环[4.4.0]癸-5-烯 作用下， 反应 72.0h， 以73%的产率得到(8-oxo-1,4-dioxaspiro[4.5]decan-7-yl) N,N-dimethylcarbamodithioate
  参考文献：
  名称：

  TBD-catalyzed α-sulfenylation of cyclic ketones: desymmetrization of 4-substituted cyclohexanones

  摘要：

  A low loading of triazabicyclo[4.4.0]dec-5-ene (TBD) catalyzes the alpha-sulfenylation reaction of ketones employing tetramethylthiuram disulfide (TMTDS) as electrophilic reagent. This methodology is mild, effective and straightforward, rendering the desired products in high yield. Prochiral 4-substituted cyclohexanones can be desymmetrized with remarkable diastereoselectivity following this protocol. The dithiocarbamoyl function was shown to be easily removed upon reduction, affording thiols (1-mercaptan-2-ols). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.124