(S)-2,2,2-trichloro-N-(1-(4-methoxyphenyl)but-3-en-2-yl)acetamide | 1163716-50-4

• 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: (S)-2,2,2-trichloro-N-(1-(4-methoxyphenyl)but-3-en-2-yl)acetamide
• 英文别名: 2,2,2-trichloro-N-[(2S)-1-(4-methoxyphenyl)but-3-en-2-yl]acetamide
• CAS: 1163716-50-4
• 化学式: C₁₃H₁₄Cl₃NO₂
• 分子量: 322.619
• InChiKey: KISNMTRZQRXNDO-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2,2,2-trichloro-N-(1-(4-methoxyphenyl)but-3-en-2-yl)acetamide 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 生成 (2S)-1-(4-methoxyphenyl)but-3-en-2-amine
  参考文献：
  名称：

  Asymmetric Synthesis of Unsaturated Monocyclic and Bicyclic Nitrogen Heterocycles

  摘要：

  Hydrolysis of scalemic trichloroacetamides Cl3CCONHCH(R)CHCH2 and allylation, or acylation with but-3-enoic acid, followed by ring-closing metathesis resulted in the formation of unsaturated pyrrolidine and piperidine building blocks. These were employed in the synthesis of (S)-coniine (R = Pr) and a formal synthesis of (+)-anisomycin (R = p-MeOC5H4). Extension of this methodology with R = CH2CHCH2 employing two ring-closing metatheses resulted in the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.

  DOI：

  10.1021/ol900880w
• 作为产物：
  描述：

  (E)-4-(4-methoxyphenyl)but-2-enyl 2,2,2-trichloroacetimidate 在 di-μ-chlorobis[(η5-(S)-(ρR)-2-(2'-(4'-methylethyl)oxazolinyl)cyclopentadienyl, 1-C,3'-N)(η4-tetraphenylcyclobutadiene)cobalt]dipalladium 作用下， 以 乙腈 为溶剂， 反应 144.0h， 以89%的产率得到(S)-2,2,2-trichloro-N-(1-(4-methoxyphenyl)but-3-en-2-yl)acetamide
  参考文献：
  名称：

  Asymmetric Synthesis of Unsaturated Monocyclic and Bicyclic Nitrogen Heterocycles

  摘要：

  Hydrolysis of scalemic trichloroacetamides Cl3CCONHCH(R)CHCH2 and allylation, or acylation with but-3-enoic acid, followed by ring-closing metathesis resulted in the formation of unsaturated pyrrolidine and piperidine building blocks. These were employed in the synthesis of (S)-coniine (R = Pr) and a formal synthesis of (+)-anisomycin (R = p-MeOC5H4). Extension of this methodology with R = CH2CHCH2 employing two ring-closing metatheses resulted in the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.

  DOI：

  10.1021/ol900880w

文献信息

• Asymmetric Synthesis of Unsaturated Monocyclic and Bicyclic Nitrogen Heterocycles
  作者：Hiroshi Nomura、Christopher J. Richards

  DOI：10.1021/ol900880w

  日期：2009.7.2

  Hydrolysis of scalemic trichloroacetamides Cl3CCONHCH(R)CHCH2 and allylation, or acylation with but-3-enoic acid, followed by ring-closing metathesis resulted in the formation of unsaturated pyrrolidine and piperidine building blocks. These were employed in the synthesis of (S)-coniine (R = Pr) and a formal synthesis of (+)-anisomycin (R = p-MeOC5H4). Extension of this methodology with R = CH2CHCH2 employing two ring-closing metatheses resulted in the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.