1-chloro-3-(4-methylbenzyloxy)-2-propanol | 13906-80-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-chloro-3-(4-methylbenzyloxy)-2-propanol
• 英文别名: 1-Chloro-3-[(4-methylphenyl)methoxy]propan-2-ol
• CAS: 13906-80-4
• 化学式: C₁₁H₁₅ClO₂
• 分子量: 214.692
• InChiKey: OWSNWAVQHMFKEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸乙烯酯 、 1-chloro-3-(4-methylbenzyloxy)-2-propanol 在 Alcaligenes sp. (PL) lipase 作用下， 以 正己烷 、 乙腈 为溶剂， 反应 30.0h， 以47%的产率得到(R)-1-chloro-3-(4-methylbenzyloxy)-2-propanol
  参考文献：
  名称：

  A new and facile preparation of tert-butyl (3R,5S)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate

  摘要：

  A facile method for the preparation of tert-butyl (3R,5S)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate is described by a chemoenzymatic approach. In this method, one hydroxyl stereocenter at C5 is obtained with a high ee value (up to 98.0%) via an enzymatic transesterification resolution of 1-chloro-3-(4-methylbenzyloxy)-2-propanol. The other hydroxyl stereocenter at C3 was built with 98.0% de, by acid-hydrolysis of a 1,3-diol-acetonide syn/anti-10. It is noteworthy that the reduction of beta-hydroxy ketone 8 with sodium borohydride can be carried out smoothly in aqueous isopropyl alcohol with a high diastereomeric ratio syn/anti (dr(s:a)) of 4.0:1. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.09.026
• 作为产物：
  描述：

  1-(4-methylbenzyloxy)-2,3-epoxypropane 在 氯化铵 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以85%的产率得到1-chloro-3-(4-methylbenzyloxy)-2-propanol
  参考文献：
  名称：

  A new and facile preparation of tert-butyl (3R,5S)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate

  摘要：

  A facile method for the preparation of tert-butyl (3R,5S)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate is described by a chemoenzymatic approach. In this method, one hydroxyl stereocenter at C5 is obtained with a high ee value (up to 98.0%) via an enzymatic transesterification resolution of 1-chloro-3-(4-methylbenzyloxy)-2-propanol. The other hydroxyl stereocenter at C3 was built with 98.0% de, by acid-hydrolysis of a 1,3-diol-acetonide syn/anti-10. It is noteworthy that the reduction of beta-hydroxy ketone 8 with sodium borohydride can be carried out smoothly in aqueous isopropyl alcohol with a high diastereomeric ratio syn/anti (dr(s:a)) of 4.0:1. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.09.026

文献信息

• Moshchinskaya,N.K. et al., Journal of Organic Chemistry USSR (English Translation), 1967, vol. 3, p. 70 - 74
  作者：Moshchinskaya,N.K. et al.

  DOI：——

  日期：——
• A new and facile preparation of tert-butyl (3R,5S)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate
  作者：Fenglai Sun、Gang Xu、Jianping Wu、Lirong Yang

  DOI：10.1016/j.tetasy.2007.09.026

  日期：2007.10

  A facile method for the preparation of tert-butyl (3R,5S)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate is described by a chemoenzymatic approach. In this method, one hydroxyl stereocenter at C5 is obtained with a high ee value (up to 98.0%) via an enzymatic transesterification resolution of 1-chloro-3-(4-methylbenzyloxy)-2-propanol. The other hydroxyl stereocenter at C3 was built with 98.0% de, by acid-hydrolysis of a 1,3-diol-acetonide syn/anti-10. It is noteworthy that the reduction of beta-hydroxy ketone 8 with sodium borohydride can be carried out smoothly in aqueous isopropyl alcohol with a high diastereomeric ratio syn/anti (dr(s:a)) of 4.0:1. (c) 2007 Elsevier Ltd. All rights reserved.