3-fluorophenyl-diphenylphosphine | 21388-29-4

• 物质功能分类: 有机原料 - 有机膦化合物
• 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: 3-fluorophenyl-diphenylphosphine
• 英文别名: Phosphine, (3-fluorophenyl)diphenyl-；(3-fluorophenyl)-diphenylphosphane
• CAS: 21388-29-4
• 化学式: C₁₈H₁₄FP
• 分子量: 280.281
• InChiKey: VVTPGMKFNKYMSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-fluorophenyl-diphenylphosphine 在 双氧水 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 (3-fluorophenyl)diphenylphosphine oxide
  参考文献：
  名称：

  Efficient synthesis of (R)- and (S)-(6,6′-difluorobiphenyl-2,2′-diyl) bis(diphenylphosphine); electron-poor biphenyl-type ligands for transition metal catalysts.

  摘要：

  Racemic title compound (RS)-5 is synthesized (Scheme 1, 100g scale) in four simple steps (49% overall yield) from meta-fluorobromobenzene 1. (RS)-5 is efficiently resolved (Scheme 2) utilizing commercial (S)-(+)-dipalladium complex 9 to give homochiral (S)-(+)-5 and (R)-(-)-5 in 75 and 95% of theoretical yield, respectively. Enantiomerically pure diphosphines (S)-5 and (R)-5 do not racemize in organic solutions, even when heated to 207 degrees C. Homochiral palladium(ll) dichloride complexes (-)-11 and (+)-11 are prepared in quantitative yield. Insitu rhodium(I)-complex of homochiral 5 is ail efficient catalyst for alkene hydroboration by catecholborane and requires high hydrogen pressure to catalyze hydrogenation.Interesting anomalies of the specific rotation are observed for homochiral diphosphines (S)-(+)5 and (R)-(-)-5. The specific rotation [alpha](25)(D) of (S)-(+)-5 measured in similar aromatic hydrocarbons (toluene, o-xylene, mesitylene, tetralin) varies from +114.9 (c 0.99, toluene) to 73.9(c 0.46, tetralin).

  DOI：

  10.1016/0957-4166(94)80172-x
• 作为产物：
  描述：

  间溴氟苯 、 二苯基氯化膦 在 正丁基锂 作用下， 生成 3-fluorophenyl-diphenylphosphine
  参考文献：
  名称：

  Efficient synthesis of (R)- and (S)-(6,6′-difluorobiphenyl-2,2′-diyl) bis(diphenylphosphine); electron-poor biphenyl-type ligands for transition metal catalysts.

  摘要：

  Racemic title compound (RS)-5 is synthesized (Scheme 1, 100g scale) in four simple steps (49% overall yield) from meta-fluorobromobenzene 1. (RS)-5 is efficiently resolved (Scheme 2) utilizing commercial (S)-(+)-dipalladium complex 9 to give homochiral (S)-(+)-5 and (R)-(-)-5 in 75 and 95% of theoretical yield, respectively. Enantiomerically pure diphosphines (S)-5 and (R)-5 do not racemize in organic solutions, even when heated to 207 degrees C. Homochiral palladium(ll) dichloride complexes (-)-11 and (+)-11 are prepared in quantitative yield. Insitu rhodium(I)-complex of homochiral 5 is ail efficient catalyst for alkene hydroboration by catecholborane and requires high hydrogen pressure to catalyze hydrogenation.Interesting anomalies of the specific rotation are observed for homochiral diphosphines (S)-(+)5 and (R)-(-)-5. The specific rotation [alpha](25)(D) of (S)-(+)-5 measured in similar aromatic hydrocarbons (toluene, o-xylene, mesitylene, tetralin) varies from +114.9 (c 0.99, toluene) to 73.9(c 0.46, tetralin).

  DOI：

  10.1016/0957-4166(94)80172-x

文献信息

• Halogenated biphenyl-2,2'-diylbisdiphenylphosphines, their preparation
  申请人：Hoechst Aktiengesellschaft

  公开号：US05621128A1

  公开（公告）日：1997-04-15

  Compounds of the formula I ##STR1## in which the phenyl rings of the biphenyl molecule can be substituted with up to 8 fluorine and/or chlorine atoms are suitable as catalysts.

  式I的化合物##STR1##中，联苯分子中的苯环可以被最多8个氟和/或氯原子取代，适用作催化剂。
• Halogenierte Biphenyl-2,2'diyl-bis-diphenylphosphine, ihre Herstellung und ihre Verwendung
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0690065A1

  公开（公告）日：1996-01-03

  Verbindungen der Formel I in der die Phenylringe des Biphenylmoleküls mit bis zu 8 Fluor- und/oder Chloratomen substituiert sein können, eignen sich als Katalysatoren.

  式 I 的化合物 其中联苯分子的苯基环最多可被 8 个氟原子和/或氯原子取代，适合用作催化剂。
• Loginova, I. V.; Polovnyak, V. K., Journal of general chemistry of the USSR, 1990, vol. 60, p. 229 - 233
  作者：Loginova, I. V.、Polovnyak, V. K.

  DOI：——

  日期：——
• Switching On and Off Metalation Sites in Triarylphosphines by Manipulating Substrate Coordination
  作者：Olivier Desponds

  DOI：10.1055/s-1998-2099

  日期：1998.7
• TOMCUFCIK, ANDREW S.;EMMA, JOHN E.;EUDY, NANCY H.;MARSICU, JOSEPH W.;NEWM+
  作者：TOMCUFCIK, ANDREW S.、EMMA, JOHN E.、EUDY, NANCY H.、MARSICU, JOSEPH W.、NEWM+

  DOI：——

  日期：——