(2Z)-1-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-3-({[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}thio)propanone O-benzyloxime | 1161881-53-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2Z)-1-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-3-({[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}thio)propanone O-benzyloxime
• 英文别名: (Z)-1-[[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-3-[[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methylsulfanyl]-N-phenylmethoxypropan-2-imine
• CAS: 1161881-53-3
• 化学式: C₂₂H₃₃NO₆S
• 分子量: 439.573
• InChiKey: ZOGWOVABPSWGON-GDOJVLBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  93
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-chloro-3-({[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}thio)propanone O-benzyloxime 、 (S)-(+)-1,2-异亚丙基甘油 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 (2Z)-1-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-3-({[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}thio)propanone O-benzyloxime 、 (2E)-1-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-3-({[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}thio)propanone O-benzyloxime
  参考文献：
  名称：

  A flexible route to new spirodioxanes, oxathianes, and morpholines

  摘要：

  This work describes a modular efficient route to 10-aza-4-thia-, 10-aza-4-oxa-, and 10-oxa-4-thia-1,7-dioxaspiro[5.5]undecanes. The synthetic pathway relies upon the iterative nucleophilic substitution of 1,3-dichloropropan-2-one O-benzyloxime by solketal derivatives. The oxime key-intermediates, submitted to an acidic deprotection-spiroacetalization process, afforded these original spiroketal compounds in three steps, few purifications, and very good yields. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.044

文献信息

• A flexible route to new spirodioxanes, oxathianes, and morpholines
  作者：Marlène Goubert、Isabelle Canet、Marie-Eve Sinibaldi

  DOI：10.1016/j.tet.2009.03.044

  日期：2009.5

  This work describes a modular efficient route to 10-aza-4-thia-, 10-aza-4-oxa-, and 10-oxa-4-thia-1,7-dioxaspiro[5.5]undecanes. The synthetic pathway relies upon the iterative nucleophilic substitution of 1,3-dichloropropan-2-one O-benzyloxime by solketal derivatives. The oxime key-intermediates, submitted to an acidic deprotection-spiroacetalization process, afforded these original spiroketal compounds in three steps, few purifications, and very good yields. (C) 2009 Elsevier Ltd. All rights reserved.