(S)-2-Methoxy-2-naphthalen-1-yl-propionic acid (S)-(1,2,3,4-tetrahydro-phenanthren-4-yl) ester | 850453-25-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (S)-2-Methoxy-2-naphthalen-1-yl-propionic acid (S)-(1,2,3,4-tetrahydro-phenanthren-4-yl) ester
• 英文别名: [(4S)-1,2,3,4-tetrahydrophenanthren-4-yl] (2S)-2-methoxy-2-naphthalen-1-ylpropanoate
• CAS: 850453-25-7
• 化学式: C₂₈H₂₆O₃
• 分子量: 410.513
• InChiKey: KXJDWUHVDNMTRR-LSYYVWMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-Methoxy-2-naphthalen-1-yl-propionic acid (S)-(1,2,3,4-tetrahydro-phenanthren-4-yl) ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以85%的产率得到(S)-(+)-1,2,3,4-tetrahydro-4-phenanthrenol
  参考文献：
  名称：

  Crystalline State Conformation of 2-Methoxy-2-(1-naphthyl)propionic Acid Ester

  摘要：

  The enantioresolution method using (S)-(+)-2-methoxy-2-(1-naphthyl)propionic acid (MalphaNP acid 1) was applied to 1,2,3,4-tetrahydro-4-phenanthrenol (4). Racemic alcohol (+/-)-4 was esterified with (S)-(+)-1 , and a diastereomeric mixture of esters formed was separated by HPLC on silica gel giving the first-eluted ester 5a and the second-eluted one 5b . Ester 5a was reduced with LiAlH4 yielding enantiopure alcohol (+)-4. A single crystal of ester 5a was subjected to X-ray crystallography to determine its absolute configuration as (S,S), and therefore to assign the S absolute configuration to (+)-4 . The most striking finding in the X-ray analysis is that the methoxyl oxygen atom is syn to the ester carbonyl oxygen even in the crystalline state. This is just the preferred conformation of MalphaNP acid esters assumed in the H-1 NMR anisotropy method. The S absolute configuration of (+)-4 was also confirmed by the CD and H-1 NMR anisotropy methods.

  DOI：

  10.1080/10242430212879
• 作为产物：
  描述：

  (+/-)-1,2,3,4-tetrahydro-4-phenanthrenol 、 (S)-(+)-2-甲氧基-2-(1-萘基)丙酸 在 4-二甲氨基吡啶 、 D(+)-10-樟脑磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以43%的产率得到(S)-2-Methoxy-2-naphthalen-1-yl-propionic acid (S)-(1,2,3,4-tetrahydro-phenanthren-4-yl) ester
  参考文献：
  名称：

  Crystalline State Conformation of 2-Methoxy-2-(1-naphthyl)propionic Acid Ester

  摘要：

  The enantioresolution method using (S)-(+)-2-methoxy-2-(1-naphthyl)propionic acid (MalphaNP acid 1) was applied to 1,2,3,4-tetrahydro-4-phenanthrenol (4). Racemic alcohol (+/-)-4 was esterified with (S)-(+)-1 , and a diastereomeric mixture of esters formed was separated by HPLC on silica gel giving the first-eluted ester 5a and the second-eluted one 5b . Ester 5a was reduced with LiAlH4 yielding enantiopure alcohol (+)-4. A single crystal of ester 5a was subjected to X-ray crystallography to determine its absolute configuration as (S,S), and therefore to assign the S absolute configuration to (+)-4 . The most striking finding in the X-ray analysis is that the methoxyl oxygen atom is syn to the ester carbonyl oxygen even in the crystalline state. This is just the preferred conformation of MalphaNP acid esters assumed in the H-1 NMR anisotropy method. The S absolute configuration of (+)-4 was also confirmed by the CD and H-1 NMR anisotropy methods.

  DOI：

  10.1080/10242430212879

文献信息

• Crystalline State Conformation of 2-Methoxy-2-(1-naphthyl)propionic Acid Ester
  作者：Takuma Fujita、Shunsuke Kuwahara、Masataka Watanabe、Nobuyuki Harada

  DOI：10.1080/10242430212879

  日期：2002.7

  The enantioresolution method using (S)-(+)-2-methoxy-2-(1-naphthyl)propionic acid (MalphaNP acid 1) was applied to 1,2,3,4-tetrahydro-4-phenanthrenol (4). Racemic alcohol (+/-)-4 was esterified with (S)-(+)-1 , and a diastereomeric mixture of esters formed was separated by HPLC on silica gel giving the first-eluted ester 5a and the second-eluted one 5b . Ester 5a was reduced with LiAlH4 yielding enantiopure alcohol (+)-4. A single crystal of ester 5a was subjected to X-ray crystallography to determine its absolute configuration as (S,S), and therefore to assign the S absolute configuration to (+)-4 . The most striking finding in the X-ray analysis is that the methoxyl oxygen atom is syn to the ester carbonyl oxygen even in the crystalline state. This is just the preferred conformation of MalphaNP acid esters assumed in the H-1 NMR anisotropy method. The S absolute configuration of (+)-4 was also confirmed by the CD and H-1 NMR anisotropy methods.