methyl (E)-6-{(2S,5S,6S)-1-[(tert-butoxy)carbonyl]-5-(methoxymethoxy)-6-methylpiperidine-2-yl}hex-5-enoate | 1451067-51-8

• 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: methyl (E)-6-{(2S,5S,6S)-1-[(tert-butoxy)carbonyl]-5-(methoxymethoxy)-6-methylpiperidine-2-yl}hex-5-enoate
• 英文别名: tert-butyl (2S,3S,6S)-3-(methoxymethoxy)-6-[(E)-6-methoxy-6-oxohex-1-enyl]-2-methylpiperidine-1-carboxylate
• CAS: 1451067-51-8
• 化学式: C₂₀H₃₅NO₆
• 分子量: 385.501
• InChiKey: BEDCIUCTQZEYHR-WMLWWBQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-已酸甲酯 、 (2S,3S,6S)-2-methyl-N-tert-butoxycarbonyl-3-methoxymethoxy-6-vinylpiperidine 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以80%的产率得到
  参考文献：
  名称：

  Total synthesis of (+)-azimine via diastereoselective aminopalladation

  摘要：

  The aminopalladation of amino allylic alcohol using Cl2Pd(MeCN)(2) in CH2Cl2 gave the 2,6-disubstituted piperidine with excellent diastereoselectivity. This compound was successfully converted into (+)-azimine (1) using cross-metathesis and Shiina macrolactonization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.083

文献信息

• Total synthesis of (+)-azimine via diastereoselective aminopalladation
  作者：Yuji Kurogome、Masaya Kogiso、Kok Kong Looi、Yasunao Hattori、Hiroyuki Konno、Mitsuru Hirota、Hidefumi Makabe

  DOI：10.1016/j.tet.2013.07.083

  日期：2013.9

  The aminopalladation of amino allylic alcohol using Cl2Pd(MeCN)(2) in CH2Cl2 gave the 2,6-disubstituted piperidine with excellent diastereoselectivity. This compound was successfully converted into (+)-azimine (1) using cross-metathesis and Shiina macrolactonization. (C) 2013 Elsevier Ltd. All rights reserved.