(S)-1,1-dimethoxy-2-hexanol | 158041-91-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1,1-dimethoxy-2-hexanol
• 英文别名: (2S)-1,1-dimethoxyhexan-2-ol
• CAS: 158041-91-9
• 化学式: C₈H₁₈O₃
• 分子量: 162.229
• InChiKey: VPLOFNSSGOHNTD-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1,1-dimethoxy-2-hexanol 在 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 7.08h， 生成 (S)-(-)-1,2-hexanediol, 2-methyl ether
  参考文献：
  名称：

  Microbial reduction of 2-keto acetals as a biocatalytic approach to the enantioselective synthesis of optically active 2-hydroxy acetals

  摘要：

  The reduction of the 2-keto acetals 1a and 1b by means of different microorganisms constitutes the biocatalytic access to optically active (46 to 100% ee) 2-hydroxy acetals, (S)-2a or (R)- and (S)-2b, representative compounds of a class of synthetically useful chiral building blocks.

  DOI：

  10.1016/s0957-4166(00)80434-6
• 作为产物：
  描述：

  1,1-二甲氧基己烷-2-酮 在 potassium 9-O-(1,2-isopropylidene-5-deoxy-α-D-xylofuranosyl)-9-boratabicyclo<3.3.1>nonane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以80%的产率得到(S)-1,1-dimethoxy-2-hexanol
  参考文献：
  名称：

  Asymmetric reduction of α-keto acetals with potassium 9-O-(1,2-isopropylidene-5-deoxy-D-xylofuranosyl)-9-boratabicyclo[3.3.1]nonane. Enantioselective synthesis of α-hydroxy acetals with high optical purities

  摘要：

  Asymmetric reduction of alpha-keto acetals with a chiral borohydride, potassiun 9-O-(1,2-isopropylidene-5-deoxy-alpha-D-xylofuranosyl)-9-boratabicyclo[3.3.1]nonane in THF at -78 degrees C provided the corresponding alpha-hydroxy acetals with 87-99% ee.

  DOI：

  10.1016/0957-4166(94)80142-8

文献信息

• First lipase catalysed resolution of epoxy enol esters
  作者：Sébastien Gravil、Henri Veschambre、Robert Chênevert、Jean Bolte

  DOI：10.1016/j.tetlet.2006.06.009

  日期：2006.8

  We report the first enzyme-catalysed kinetic resolution of epoxy enol esters. The lipase-promoted hydrolysis of these compounds provided alpha-hydroxyketones or alpha-hydroxyaldehydes (arising from the spontaneous rearrangement of the epoxy enols) and the residual esters with moderate to good enantioselectivity (E up to 100). (c) 2006 Elsevier Ltd. All rights reserved.
• Microbial reduction of 2-keto acetals as a biocatalytic approach to the enantioselective synthesis of optically active 2-hydroxy acetals
  作者：Patrizia Ferraboschi、Enzo Santaniello、Marco Tingoli、Fabrizio Aragozzini、Francesco Molinari

  DOI：10.1016/s0957-4166(00)80434-6

  日期：1993.8

  The reduction of the 2-keto acetals 1a and 1b by means of different microorganisms constitutes the biocatalytic access to optically active (46 to 100% ee) 2-hydroxy acetals, (S)-2a or (R)- and (S)-2b, representative compounds of a class of synthetically useful chiral building blocks.
• Asymmetric reduction of α-keto acetals with potassium 9-O-(1,2-isopropylidene-5-deoxy-D-xylofuranosyl)-9-boratabicyclo[3.3.1]nonane. Enantioselective synthesis of α-hydroxy acetals with high optical purities
  作者：Byung Tae Cho、Yu Sung Chun

  DOI：10.1016/0957-4166(94)80142-8

  日期：1994.7

  Asymmetric reduction of alpha-keto acetals with a chiral borohydride, potassiun 9-O-(1,2-isopropylidene-5-deoxy-alpha-D-xylofuranosyl)-9-boratabicyclo[3.3.1]nonane in THF at -78 degrees C provided the corresponding alpha-hydroxy acetals with 87-99% ee.