(2S,3R,Z)-2-Phenyl-3-{N-[13′′-(pyridin-3′′′-yl)tridecyl]amino}-16-(pyridin-3′-yl)hexadec-13-enoic acid | 945979-01-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3R,Z)-2-Phenyl-3-{N-[13′′-(pyridin-3′′′-yl)tridecyl]amino}-16-(pyridin-3′-yl)hexadec-13-enoic acid
• 英文别名: (-)-(2S,3R,Z)-nakinadine A；(Z,2S,3R)-2-phenyl-16-pyridin-3-yl-3-(13-pyridin-3-yltridecylamino)hexadec-13-enoic acid
• CAS: 945979-01-1
• 化学式: C₄₅H₆₇N₃O₂
• 分子量: 682.046
• InChiKey: TYCDSXYCBIVNDY-BATCFJHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  50
• 可旋转键数：
  31
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  75.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z)-14-(pyridin-3'-yl)tetradec-11-enal 在 盐酸 、 甲基溴化镁 、 4-甲基苯磺酸吡啶 、 三乙酰氧基硼氢化钠 、 magnesium sulfate 、 溶剂黄146 、 magnesium bromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 121.08h， 生成 (2S,3R,Z)-2-Phenyl-3-{N-[13′′-(pyridin-3′′′-yl)tridecyl]amino}-16-(pyridin-3′-yl)hexadec-13-enoic acid
  参考文献：
  名称：

  （-）-（2 S，3 R，Z）-那金那汀A：第一不对称合成和绝对构型分配

  摘要：

  与甲基苯乙酸的曼尼希型反应ñ -叔丁基亚亚胺从（派生- [R ）-叔-butylsulfinamide和（Ž）-14-（吡啶-3'-基）十四碳-11-烯醛已被用作关键制备2，3-顺-和2，3-抗-非对映异构体两者；（-）-那金那汀A的第一不对称合成中的步骤。光谱和特定旋转数据的比较有助于在天然产物中分配绝对（2 S，3 R，Z）-构型。（−）-（2 S，3 R，Z）-那金那定A由11-溴苯甲酰胺-1-醇分10步制备，总产率为10％，dr [（Z）:( E）比]为97：3 dr，ee≥98 ％。

  DOI：

  10.1021/ol500096r

文献信息

• Asymmetric Syntheses of Nakinadine D, Nakinadine E, and Nakinadine F: Confirmation of Their Relative (<i>RS</i>,<i>SR</i>)-Configurations and Proposal of Their Absolute (2<i>S</i>,3<i>R</i>)-Configurations
  作者：Stephen G. Davies、Ai M. Fletcher、Rushabh S. Shah、Paul M. Roberts、James E. Thomson

  DOI：10.1021/acs.joc.5b00376

  日期：2015.4.17

  The syn- and anti-diastereoisomeric forms of the reported structures of the marine alkaloids nakinadines DF have been synthesized, for the first time in all cases, via an approach involving asymmetric Mannich-type (imino-aldol) reactions of methyl phenylacetate with N-tert-butylsulfinyl imines as the key steps to control the stereochemistry. Comparison of the H-1 and C-13 NMR spectroscopic data reported for the natural materials with those acquired for these synthetic samples confirms the initially assigned relative (RS,SR)-configurations of these three alkaloids. In the absence of specific rotation (or other diagnostic) data for the natural materials, it is not possible to unambiguously assign their absolute configurations, although given the absolute (2S)-configurations assigned to nakinadines B and C, and the absolute (2S,3R)-configuration previously established for nakinadine A, the data herein uphold our proposal that nakinadines DF share the absolute (2S,3R)-configuration.
• (−)-(2<i>S</i>,3<i>R</i>,<i>Z</i>)-Nakinadine A: First Asymmetric Synthesis and Absolute Configuration Assignment
  作者：Stephen G. Davies、Ai M. Fletcher、Paul M. Roberts、Rushabh S. Shah、Amber L. Thompson、James E. Thomson

  DOI：10.1021/ol500096r

  日期：2014.3.7

  (Z)-14-(pyridin-3′-yl)tetradec-11-enal has been used as the key step in the first asymmetric synthesis of (−)-nakinadine A. Both the 2,3-syn- and 2,3-anti-diastereoisomers were prepared; comparison of spectroscopic and specific rotation data facilitated assignment of the absolute (2S,3R,Z)-configuration within the natural product. (−)-(2S,3R,Z)-Nakinadine A was prepared in 10 steps from 11-bromoundecan-1-ol

  与甲基苯乙酸的曼尼希型反应ñ -叔丁基亚亚胺从（派生- [R ）-叔-butylsulfinamide和（Ž）-14-（吡啶-3'-基）十四碳-11-烯醛已被用作关键制备2，3-顺-和2，3-抗-非对映异构体两者；（-）-那金那汀A的第一不对称合成中的步骤。光谱和特定旋转数据的比较有助于在天然产物中分配绝对（2 S，3 R，Z）-构型。（−）-（2 S，3 R，Z）-那金那定A由11-溴苯甲酰胺-1-醇分10步制备，总产率为10％，dr [（Z）:( E）比]为97：3 dr，ee≥98 ％。