N-Boc-N-allyl-cis-cinnamylamine | 219668-54-9

• 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: N-Boc-N-allyl-cis-cinnamylamine
• 英文别名: tert-butyl N-[(Z)-3-phenylprop-2-enyl]-N-prop-2-enylcarbamate
• CAS: 219668-54-9
• 化学式: C₁₇H₂₃NO₂
• 分子量: 273.375
• InChiKey: UPPWUIQBGVXPGN-XFXZXTDPSA-N

物化性质

• 沸点：
  379.4±32.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Boc-N-allyl-cis-cinnamylamine 在 <(c-C6H11)2(c-Me2NClC5H9)P>2Cl2Ru=CHPh 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 N-Boc-3-吡咯啉
  参考文献：
  名称：

  Ring-Closing Metathesis in Methanol and Water

  摘要：

  The ring-closing metathesis (RCM) of acyclic dienes in both methanol and water has been achieved through the use of water-soluble ruthenium alkylidenes. These alkylidenes react readily with acyclic olefins in protic solvents, but they do not cyclize alpha,omega-dienes because of the instability of the resulting methylidene. Successful cyclization has been achieved through simple substrate modification-incorporation of an olefin substituent allows cyclization to proceed in good yield. A methyl-substituted substrate was cyclized in 60% conversion in methanol, and the incorporation of a phenyl substituent resulted in nearly quantitative cyclization. Phenyl-substituted substrates are best suited for the reaction, as a more stable, active catalyst is regenerated upon each catalyst turnover. Using this methodology, 90% conversion of a water-soluble substrate to a substituted cyclopentene has been achieved in aqueous solution. This methodology has also been successfully applied to increase RCM yields in organic solvents.

  DOI：

  10.1021/jo981678o
• 作为产物：
  描述：

  (Z)-肉桂醇 在 四溴化碳 、 sodium hydride 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-Boc-N-allyl-cis-cinnamylamine
  参考文献：
  名称：

  Ring-Closing Metathesis in Methanol and Water

  摘要：

  The ring-closing metathesis (RCM) of acyclic dienes in both methanol and water has been achieved through the use of water-soluble ruthenium alkylidenes. These alkylidenes react readily with acyclic olefins in protic solvents, but they do not cyclize alpha,omega-dienes because of the instability of the resulting methylidene. Successful cyclization has been achieved through simple substrate modification-incorporation of an olefin substituent allows cyclization to proceed in good yield. A methyl-substituted substrate was cyclized in 60% conversion in methanol, and the incorporation of a phenyl substituent resulted in nearly quantitative cyclization. Phenyl-substituted substrates are best suited for the reaction, as a more stable, active catalyst is regenerated upon each catalyst turnover. Using this methodology, 90% conversion of a water-soluble substrate to a substituted cyclopentene has been achieved in aqueous solution. This methodology has also been successfully applied to increase RCM yields in organic solvents.

  DOI：

  10.1021/jo981678o

文献信息

• Ring-Closing Metathesis in Methanol and Water
  作者：Thomas A. Kirkland、David M. Lynn、Robert H. Grubbs

  DOI：10.1021/jo981678o

  日期：1998.12.1

  The ring-closing metathesis (RCM) of acyclic dienes in both methanol and water has been achieved through the use of water-soluble ruthenium alkylidenes. These alkylidenes react readily with acyclic olefins in protic solvents, but they do not cyclize alpha,omega-dienes because of the instability of the resulting methylidene. Successful cyclization has been achieved through simple substrate modification-incorporation of an olefin substituent allows cyclization to proceed in good yield. A methyl-substituted substrate was cyclized in 60% conversion in methanol, and the incorporation of a phenyl substituent resulted in nearly quantitative cyclization. Phenyl-substituted substrates are best suited for the reaction, as a more stable, active catalyst is regenerated upon each catalyst turnover. Using this methodology, 90% conversion of a water-soluble substrate to a substituted cyclopentene has been achieved in aqueous solution. This methodology has also been successfully applied to increase RCM yields in organic solvents.