(3R,4R)-3,4-dimethoxy-1-phenylphospholane | 115952-07-3

• 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: (3R,4R)-3,4-dimethoxy-1-phenylphospholane
• 英文别名: 1-phenyl-3,4-dimethoxyphospholane；(R,R)-(+)-phenyl-tarpholane
• CAS: 115952-07-3
• 化学式: C₁₂H₁₇O₂P
• 分子量: 224.24
• InChiKey: LYIOZBAVYYDWTH-RYUDHWBXSA-N

物化性质

• 沸点：
  313.2±42.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 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：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3,4-dimethoxy-1-phenylphospholane 在 双氧水 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以13.0 mg的产率得到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
• 作为产物：
  描述：

  苯基膦酸二乙酯 在 palladium dihydroxide 四溴化碳 、 氢气 、 三苯基膦 、 红铝 作用下， 以 乙醇 、 氯仿 、 甲苯 为溶剂， 反应 15.75h， 生成 (3R,4R)-3,4-dimethoxy-1-phenylphospholane
  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

• Optically active transition metal compounds 113
  作者：Henri Brunner、Peter Faustmann、Bernhard Nuber

  DOI：10.1016/s0022-328x(97)00745-6

  日期：1998.4

  diastereomers of 1 (L=P(OMe)3, L*=PPh2N(Me)CH(Me)(Ph)), 2 (L=PPh3, L*=CNCH(Me)(Ph)), 7 (L=PMe2Ph, L*=glyphos) and 8. The ratios achieved are 74:26 (1a:1b), 79:21 (2a:2b), 71:29 (7a:7b) and 74:26 (8a:8b). The crystal structures of six complexes were determined. For (SCo,SC)-2a, (RCo,SC)-3b and (SCo,RC,RC)-8a the absolute configuration could be established. The cobalt center is configurationally stable at room

  在两步合成中，从Co（CO）3（NO）中获得了仅在钴原子上的构型不同的非对映异构体Co（CO）（NO）（L）（L * ）。L是单齿亚磷酸酯或膦，而L *是单齿光学活性膦或异氰化物。对于复杂的8（L = PPH 3，L =苯基tarpholane）的55:45非对映体之比（图8a：图8b）在合成后发现。对于所有其他配合物，该比例为50:50。通过结晶，可以获得富集了以下一种非对映异构体的样品：1（L = P（OMe）3，L * = PPh 2 N（Me）CH（Me）（Ph）），2（L = PPh 3， L * = CNCH（Me）（Ph）），图7（L ＝ PMe 2 Ph，L * ＝草甘膦）和8。达到的比例为74:26（1a：1b），79:21（2a：2b），71 : 29（7a：7b）和74:26（8a：8b）。确定了六个配合物的晶体结构。对于（S Co，S C）-2a，（R Co，S C）-3b和（S
• Asymmetric catalyses
  作者：Henri Brunner、Robert Sievi

  DOI：10.1016/s0022-328x(00)99768-7

  日期：1987.7
• 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).
• 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).