3-hex-5-enyl-5-[1-hex-5-enyl-5-[(E)-7-hydroxyhept-2-enyl]-3,6-dihydro-2H-pyridin-4-yl]-1-(5-phenylmethoxypentyl)-3,4-dihydropyridin-2-one | 1220119-81-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-hex-5-enyl-5-[1-hex-5-enyl-5-[(E)-7-hydroxyhept-2-enyl]-3,6-dihydro-2H-pyridin-4-yl]-1-(5-phenylmethoxypentyl)-3,4-dihydropyridin-2-one
• CAS: 1220119-81-2
• 化学式: C₄₁H₆₂N₂O₃
• 分子量: 630.955
• InChiKey: BYZOQDABXCWDJH-LICLKQGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  46
• 可旋转键数：
  25
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hex-5-enyl-5-[1-hex-5-enyl-5-[(E)-7-hydroxyhept-2-enyl]-3,6-dihydro-2H-pyridin-4-yl]-1-(5-phenylmethoxypentyl)-3,4-dihydropyridin-2-one 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Total Synthesis of (±)-Haliclonacyclamine C

  摘要：

  DOI：

  10.1002/anie.200905732
• 作为产物：
  描述：

  [1-hex-5-enyl-4-[3-hex-5-enyl-2-oxo-1-(5-phenylmethoxypentyl)-3,4-dihydropyridin-5-yl]-3,6-dihydro-2H-pyridin-5-yl]methyl acetate 、 (E)-6-(tributylstannyl)hex-5-en-1-ol 在 lithium chloride 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到3-hex-5-enyl-5-[1-hex-5-enyl-5-[(E)-7-hydroxyhept-2-enyl]-3,6-dihydro-2H-pyridin-4-yl]-1-(5-phenylmethoxypentyl)-3,4-dihydropyridin-2-one
  参考文献：
  名称：

  Synthesis and bioactivity of (±)-tetrahydrohaliclonacyclamine A

  摘要：

  The total synthesis of tetrahydrohaliclonacyclamine A (5) is described. A key step involves the hydrogenation of an unsaturated bis-piperidine incorporated into a 17-membered macrocycle to provide the cis-syn-cis stereochemistry common to haliclonacyclamines A-D. The hydrogenation product is advanced to the title compound following a five-step reaction sequence. Tetrahydrohaliclonacyclamine A is shown to bind to a variety of ion channels/GPCRs and act as a muscarinic M-1 antagonist. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.117

文献信息

• Synthesis and bioactivity of (±)-tetrahydrohaliclonacyclamine A
  作者：Brian J. Smith、Tao Qu、Matthew Mulder、Meredith J. Noetzel、Craig W. Lindsley、Gary A. Sulikowski

  DOI：10.1016/j.tet.2010.03.117

  日期：2010.6

  The total synthesis of tetrahydrohaliclonacyclamine A (5) is described. A key step involves the hydrogenation of an unsaturated bis-piperidine incorporated into a 17-membered macrocycle to provide the cis-syn-cis stereochemistry common to haliclonacyclamines A-D. The hydrogenation product is advanced to the title compound following a five-step reaction sequence. Tetrahydrohaliclonacyclamine A is shown to bind to a variety of ion channels/GPCRs and act as a muscarinic M-1 antagonist. (C) 2010 Elsevier Ltd. All rights reserved.
• Total Synthesis of (±)-Haliclonacyclamine C
  作者：Brian J. Smith、Gary A. Sulikowski

  DOI：10.1002/anie.200905732

  日期：2010.2.22