(R)-2-[(2R,4aS,8R,8aS)-8-(2-chloroacetamido)-4a,8-dimethyldecahydronaphthalen-2-yl]propyl methanesulfonate | 929285-22-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (R)-2-[(2R,4aS,8R,8aS)-8-(2-chloroacetamido)-4a,8-dimethyldecahydronaphthalen-2-yl]propyl methanesulfonate
• 英文别名: [(2R)-2-[(2R,4aS,8R,8aS)-8-[(2-chloroacetyl)amino]-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]propyl] methanesulfonate
• CAS: 929285-22-3
• 化学式: C₁₈H₃₂ClNO₄S
• 分子量: 393.975
• InChiKey: SDPCWBOZFYKFQU-UXDQUXDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-[(2R,4aS,8R,8aS)-8-(2-chloroacetamido)-4a,8-dimethyldecahydronaphthalen-2-yl]propyl methanesulfonate 在 lithium carbonate 、 溶剂黄146 、 硫脲 、 lithium bromide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.75h， 生成 (-)-4-epiaxinyssamine hydrochloride
  参考文献：
  名称：

  Stereoselective synthesis of (–)-4-epiaxinyssamine

  摘要：

  The synthetic studies towards axinyssamine, a cytotoxic and coral-lethal compound isolated from the Caribbean sponge Axinyssa ambrosia were performed. The Ritter reaction on the key intermediate with chloroacetonitrile, resulted in the introduction of the amino group at C-4 generating the configuration of this stereocentre opposite to that of the natural product. As a result, the first total synthesis of the unnatural (-)-4-epiaxinyssamine was achieved. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.019
• 作为产物：
  描述：

  (1R,4aR,7R,8aR)-8a-hydroxy-1,4a-dimethyl-7-(prop-1-en-2-yl)-octahydronaphthalen-2(1H)-one 在 吡啶 、 氢氧化钾 、 甲酸 、 硼烷四氢呋喃络合物 、 硫酸 、 氨 、 lithium 、 lithium carbonate 、 lithium bromide 、 叔丁醇 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.75h， 生成 (R)-2-[(2R,4aS,8R,8aS)-8-(2-chloroacetamido)-4a,8-dimethyldecahydronaphthalen-2-yl]propyl methanesulfonate
  参考文献：
  名称：

  Stereoselective synthesis of (–)-4-epiaxinyssamine

  摘要：

  The synthetic studies towards axinyssamine, a cytotoxic and coral-lethal compound isolated from the Caribbean sponge Axinyssa ambrosia were performed. The Ritter reaction on the key intermediate with chloroacetonitrile, resulted in the introduction of the amino group at C-4 generating the configuration of this stereocentre opposite to that of the natural product. As a result, the first total synthesis of the unnatural (-)-4-epiaxinyssamine was achieved. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.019

文献信息

• Stereoselective synthesis of (–)-4-epiaxinyssamine
  作者：Leonardo Castellanos、Carmenza Duque、Jaime Rodríguez、Carlos Jiménez

  DOI：10.1016/j.tet.2006.12.019

  日期：2007.2

  The synthetic studies towards axinyssamine, a cytotoxic and coral-lethal compound isolated from the Caribbean sponge Axinyssa ambrosia were performed. The Ritter reaction on the key intermediate with chloroacetonitrile, resulted in the introduction of the amino group at C-4 generating the configuration of this stereocentre opposite to that of the natural product. As a result, the first total synthesis of the unnatural (-)-4-epiaxinyssamine was achieved. (c) 2006 Elsevier Ltd. All rights reserved.