methyl (2R,3R,R_S,Z)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadec-13-enoate | 1569300-01-1

• 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: methyl (2R,3R,R_S,Z)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadec-13-enoate
• CAS: 1569300-01-1
• 化学式: C₃₂H₄₈N₂O₃S
• 分子量: 540.811
• InChiKey: QUKDAGQTSHYZPW-GLMHQYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.46
• 重原子数：
  38.0
• 可旋转键数：
  18.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  68.29
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (2R,3R,R_S,Z)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadec-13-enoate 在 盐酸 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 18.08h， 生成 Methyl (2R,3R,Z)-2-phenyl-3-{N-[13′′-(pyridin-3′′′-yl)tridecyl]amino}-16-(pyridin-3′-yl)hexadec-13-enoate
  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
• 作为产物：
  描述：

  methyl (2S,3R,RS,Z)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadec-13-enoate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以60%的产率得到methyl (2R,3R,R_S,Z)-2-phenyl-3-(N-tert-butylsulfinamido)-16-(pyridin-3′-yl)hexadec-13-enoate
  参考文献：
  名称：

  Asymmetric Syntheses of Nakinadine D, Nakinadine E, and Nakinadine F: Confirmation of Their Relative (RS,SR)-Configurations and Proposal of Their Absolute (2S,3R)-Configurations

  摘要：

  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.

  DOI：

  10.1021/acs.joc.5b00376