1,4-dideoxy-2,3-di-O-methyl-1,4-phenylphosphonoyl-L-threitol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,4-dideoxy-2,3-di-O-methyl-1,4-phenylphosphonoyl-L-threitol
• 英文别名: (3R,4R)-3,4-dimethoxy-1-phenylphospholane 1-oxide；(3R,4R)-3,4-dimethoxy-1-phenylphospholane-1-oxide；(3R,4R)-3,4-dimethoxy-1-phenyl-1λ5-phospholane 1-oxide
• 化学式: C₁₂H₁₇O₃P
• 分子量: 240.239
• InChiKey: JPFWYODSZLTWFL-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯基膦酸二乙酯 在 palladium dihydroxide 四溴化碳 、 氢气 、 magnesium 、 1,2-二溴乙烷 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 为溶剂， 反应 13.25h， 生成 1,4-dideoxy-2,3-di-O-methyl-1,4-phenylphosphonoyl-L-threitol
  参考文献：
  名称：

  Synthesis of Phospholane 1-Oxide Having Oxygen Functional Groups from a 4-Bromobutylphoshinate Derivative

  摘要：

  Ethyl 4-bromo-2,3-dimethoxybutyl(phenyl)phosphinate (10a) was prepared from 2,3-di-0-methyl-L-threitol (12) in five steps. Reduction of 10a with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrogen peroxide, afforded 3,4-dimethoxy-1-phenylphospholane I-oxide (3), while the reaction of 10a with magnesium in boiling THF resulted in the formation of ethyl 2-methoxy-3-butenyl(phenyl)phosphinate (26).

  DOI：

  10.3987/com-05-s(k)15

文献信息

• Synthesis of Functionalized Phospholane Oxides and Phosphorinane Oxides from 1,4- and 1,5-Di-O-Mesyloxy Compounds
  作者：Tadashi Hanaya、Karsten Schürrle、Hiroshi Yamamoto

  DOI：10.3987/com-06-s(o)28

  日期：——

  Treatment of 1,4-di-0-mesyl-2,3-di-O-methyl-L-threitol (8b) with phenylphosphine in the presence of sodium hydride in DMSO, followed by the action of hydrogen peroxide, afforded 3,4-dimethoxy-1-phenylphospholane 1-oxide (7), while the same treatment of 1,5-di-O-mesyl-2,3,4-tri-O-methyl-mesoxylitol (11b) provided 2,3,4-trimethoxy-1-phenylphosphorinane 1-oxide (14).
• Synthesis of Phospholane 1-Oxide Having Oxygen Functional Groups from a 4-Bromobutylphoshinate Derivative
  作者：Tadashi Hanaya、Shigeru Kawase、Hiroshi Yamamoto

  DOI：10.3987/com-05-s(k)15

  日期：——

  Ethyl 4-bromo-2,3-dimethoxybutyl(phenyl)phosphinate (10a) was prepared from 2,3-di-0-methyl-L-threitol (12) in five steps. Reduction of 10a with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrogen peroxide, afforded 3,4-dimethoxy-1-phenylphospholane I-oxide (3), while the reaction of 10a with magnesium in boiling THF resulted in the formation of ethyl 2-methoxy-3-butenyl(phenyl)phosphinate (26).