[(3S)-oct-1-en-3-yl] (2S)-2-methoxy-2-phenanthren-9-ylpropanoate | 866408-82-4

• 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: [(3S)-oct-1-en-3-yl] (2S)-2-methoxy-2-phenanthren-9-ylpropanoate
• CAS: 866408-82-4
• 化学式: C₂₆H₃₀O₃
• 分子量: 390.522
• InChiKey: HQQXTXJEZZCZRD-IBVKSMDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  [(3S)-oct-1-en-3-yl] (2S)-2-methoxy-2-phenanthren-9-ylpropanoate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以80%的产率得到(S)-(+)-1-辛烯-3-醇
  参考文献：
  名称：

  Preparation of single-enantiomer semiochemicals using 2-methoxy-2-(1-naphthyl)propionic acid and 2-methoxy-2-(9-phenanthryl)propionic acid

  摘要：

  Enantioresolution of 3-octanol, 6-methyl-5-hepten-2-ol (sulcatol), and 1-octen-3-ol was conducted using (S)-(+)-2-methoxy-2-(1-naphthyl)propionic acid (M alpha NP acid) and (S)-(+)-2-methoxy-2-(9-phenanthryl)propionic acid (M9PP acid). In each case, the diastereomeric esters obtained were readily separated by HPLC. The stereochemistry of the esters could be assigned from their respective H-1 NMR analyses. Solvolyses of the esters gave enantiopure alcohols and acids. M alpha NP and M9PP acids displayed almost equivalent properties in H NMR anisotropy. The chiral resolving ability of M9PP acid was slightly superior to that of MaNP acid in HPLC. alpha 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.05.036
• 作为产物：
  描述：

  1-辛烯-3-醇 、 (S)-(+)-2-methoxy-2-(9-phenanthryl)propionic acid 在 4-二甲氨基吡啶 、 (+)-10-camphorsulfonic acid 、 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[(3R)-oct-1-en-3-yl] (2S)-2-methoxy-2-phenanthren-9-ylpropanoate
  参考文献：
  名称：

  Preparation of single-enantiomer semiochemicals using 2-methoxy-2-(1-naphthyl)propionic acid and 2-methoxy-2-(9-phenanthryl)propionic acid

  摘要：

  Enantioresolution of 3-octanol, 6-methyl-5-hepten-2-ol (sulcatol), and 1-octen-3-ol was conducted using (S)-(+)-2-methoxy-2-(1-naphthyl)propionic acid (M alpha NP acid) and (S)-(+)-2-methoxy-2-(9-phenanthryl)propionic acid (M9PP acid). In each case, the diastereomeric esters obtained were readily separated by HPLC. The stereochemistry of the esters could be assigned from their respective H-1 NMR analyses. Solvolyses of the esters gave enantiopure alcohols and acids. M alpha NP and M9PP acids displayed almost equivalent properties in H NMR anisotropy. The chiral resolving ability of M9PP acid was slightly superior to that of MaNP acid in HPLC. alpha 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.05.036

文献信息

• Preparation of single-enantiomer semiochemicals using 2-methoxy-2-(1-naphthyl)propionic acid and 2-methoxy-2-(9-phenanthryl)propionic acid
  作者：Akio Ichikawa、Hiroshi Ono

  DOI：10.1016/j.tetasy.2005.05.036

  日期：2005.8

  Enantioresolution of 3-octanol, 6-methyl-5-hepten-2-ol (sulcatol), and 1-octen-3-ol was conducted using (S)-(+)-2-methoxy-2-(1-naphthyl)propionic acid (M alpha NP acid) and (S)-(+)-2-methoxy-2-(9-phenanthryl)propionic acid (M9PP acid). In each case, the diastereomeric esters obtained were readily separated by HPLC. The stereochemistry of the esters could be assigned from their respective H-1 NMR analyses. Solvolyses of the esters gave enantiopure alcohols and acids. M alpha NP and M9PP acids displayed almost equivalent properties in H NMR anisotropy. The chiral resolving ability of M9PP acid was slightly superior to that of MaNP acid in HPLC. alpha 2005 Elsevier Ltd. All rights reserved.