((2S,6R)-6-vinylpiperidin-2-yl)methanol | 957143-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: ((2S,6R)-6-vinylpiperidin-2-yl)methanol
• 英文别名: [(2S,6R)-6-ethenylpiperidin-2-yl]methanol
• CAS: 957143-45-2
• 化学式: C₈H₁₅NO
• 分子量: 141.213
• InChiKey: SUNRLCLAILASGB-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ((2S,6R)-6-vinylpiperidin-2-yl)methanol 、 乙烯基乙酸 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 以79%的产率得到1-((2S,6R)-2-hydroxymethyl-6-vinylpiperidin-1-yl)but-3-en-1-one
  参考文献：
  名称：

  A chemoenzymatic-RCM strategy for the enantioselective synthesis of new dihydroxylated 5-hydroxymethyl-indolizidines and 6-hydroxymethyl-quinolizidines

  摘要：

  A direct method for the synthesis of new azasugars-like compounds has been developed, which involves a new biocatalytic protocol based on the use of a lipase from Candida Cylindracea and of a ionic liquid as reaction medium, to prepare the key Cl-symmetric piperidine precursor. By subsequent application of RCM reactions and OSO4-catalyzed double bond syn-dihydroxylation, the synthesis of the target compounds could be accomplished in a straightforward and stereocontrolled manner. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.07.017
• 作为产物：
  描述：

  (2S,6R)-2-acetoxymethyl-6-vinylpiperidine-1-carboxylic acid benzyl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 40.0h， 以86%的产率得到((2S,6R)-6-vinylpiperidin-2-yl)methanol
  参考文献：
  名称：

  A chemoenzymatic-RCM strategy for the enantioselective synthesis of new dihydroxylated 5-hydroxymethyl-indolizidines and 6-hydroxymethyl-quinolizidines

  摘要：

  A direct method for the synthesis of new azasugars-like compounds has been developed, which involves a new biocatalytic protocol based on the use of a lipase from Candida Cylindracea and of a ionic liquid as reaction medium, to prepare the key Cl-symmetric piperidine precursor. By subsequent application of RCM reactions and OSO4-catalyzed double bond syn-dihydroxylation, the synthesis of the target compounds could be accomplished in a straightforward and stereocontrolled manner. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.07.017

文献信息

• A chemoenzymatic-RCM strategy for the enantioselective synthesis of new dihydroxylated 5-hydroxymethyl-indolizidines and 6-hydroxymethyl-quinolizidines
  作者：Giordano Lesma、Alessia Colombo、Nicola Landoni、Alessandro Sacchetti、Alessandra Silvani

  DOI：10.1016/j.tetasy.2007.07.017

  日期：2007.8

  A direct method for the synthesis of new azasugars-like compounds has been developed, which involves a new biocatalytic protocol based on the use of a lipase from Candida Cylindracea and of a ionic liquid as reaction medium, to prepare the key Cl-symmetric piperidine precursor. By subsequent application of RCM reactions and OSO4-catalyzed double bond syn-dihydroxylation, the synthesis of the target compounds could be accomplished in a straightforward and stereocontrolled manner. (c) 2007 Elsevier Ltd. All rights reserved.