(2S)-1-[2-(8-bromooctyl)-1,3-dithian-2-yl]propan-2-ol | 206124-10-9

• 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: (2S)-1-[2-(8-bromooctyl)-1,3-dithian-2-yl]propan-2-ol
• CAS: 206124-10-9
• 化学式: C₁₅H₂₉BrOS₂
• 分子量: 369.431
• InChiKey: IQCIBZVETXTQJD-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-1-[2-(8-bromooctyl)-1,3-dithian-2-yl]propan-2-ol 在 W-2 Raney Ni 氢氧化钾 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 24.0h， 生成 (R)-13-Methyl-oxacyclotridecan-2-one
  参考文献：
  名称：

  Synthesis of Both Enantiomers of Four Different Macrocyclic Lactones

  摘要：

  Both enantiomers of macrocyclic lactones, 12-tridecanolide (1), 13-tetradecanolide (2), 14-pentadecanolide (3) and 15-hexadecanolide (4), were synthesized utilizing (S)-(-)-beta-hydroxythioacetal (5) as the chiral building block. Key steps are the C-alkylation of a dianion derived from 5 with alkyl dibromides followed by conversion of functional groups and the two macrolactonization. The both enantiomers of 1 similar to 4 have been obtained by reductive desulfurization of the dithiane moiety.

  DOI：

  10.3987/com-97-7991
• 作为产物：
  描述：

  1-(1,3-dithian-2-yl)-2-propanone 在 正丁基锂 、 baker's yeast 作用下， 以 四氢呋喃 为溶剂， 生成 (2S)-1-[2-(8-bromooctyl)-1,3-dithian-2-yl]propan-2-ol
  参考文献：
  名称：

  Synthesis of Both Enantiomers of Four Different Macrocyclic Lactones

  摘要：

  Both enantiomers of macrocyclic lactones, 12-tridecanolide (1), 13-tetradecanolide (2), 14-pentadecanolide (3) and 15-hexadecanolide (4), were synthesized utilizing (S)-(-)-beta-hydroxythioacetal (5) as the chiral building block. Key steps are the C-alkylation of a dianion derived from 5 with alkyl dibromides followed by conversion of functional groups and the two macrolactonization. The both enantiomers of 1 similar to 4 have been obtained by reductive desulfurization of the dithiane moiety.

  DOI：

  10.3987/com-97-7991

文献信息

• Synthesis of Both Enantiomers of Four Different Macrocyclic Lactones
  作者：Yoshihiro Noda、Hitoshi Kashin

  DOI：10.3987/com-97-7991

  日期：——

  Both enantiomers of macrocyclic lactones, 12-tridecanolide (1), 13-tetradecanolide (2), 14-pentadecanolide (3) and 15-hexadecanolide (4), were synthesized utilizing (S)-(-)-beta-hydroxythioacetal (5) as the chiral building block. Key steps are the C-alkylation of a dianion derived from 5 with alkyl dibromides followed by conversion of functional groups and the two macrolactonization. The both enantiomers of 1 similar to 4 have been obtained by reductive desulfurization of the dithiane moiety.