(1-cyclopentenyl)-diphenylphosphine oxide | 38868-18-7

• 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-cyclopentenyl)-diphenylphosphine oxide
• 英文别名: [cyclopenten-1-yl(phenyl)phosphoryl]benzene
• CAS: 38868-18-7
• 化学式: C₁₇H₁₇OP
• 分子量: 268.295
• InChiKey: KDOUMJHJYRFPHI-UHFFFAOYSA-N

物化性质

• 熔点：
  111-113 °C
• 沸点：
  457.4±28.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (1-cyclopentenyl)-diphenylphosphine oxide 在 potassium permanganate 、 ammonium cerium(IV) nitrate 、 四甲基乙二胺 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 生成 trans-(2-diphenylphosphinyl)cyclopentanecarboxylic acid
  参考文献：
  名称：

  Synthesis of a novel type of chiral phosphinocarboxylic acids. The phosphine-palladium complexes catalyzed asymmetric allylic alkylation

  摘要：

  A novel type of chiral cycloalkylphosphines bearing the carboxy group at the beta-position were developed, and used for palladium catalyzed asymmetric alkylation of allylic substrates such as 2-cyclohexenylacetate and 1,3-disubstituted-propenyl acetates (R1CH = CHCH(OAc)R2: R1 = R2 = Ph; R1 = Ph, R2 = (CH2)4OAc; R1 = Ph, R2 = (CH2)6OAc; R1 = Ph, R2 = (CH2)10OAc). Reaction of the propenyl acetates with soft carbon nucleophiles such as triethyl sodiophosphonoacetate and sodiomalonic acid esters in the presence of a palladium catalyst prepared in situ from Pd(OAc)2 and chiral (2-diphenylphosphino)cycloalkanecarboxylic acids (7a,b) gave high yields of alkylation products (PhCH = CHCH(X)Ph: > 77 %ee for X = CH(CO2Et)P(O)(OEt)2 and > 72 %ee for X = CH(CO2Me)2). The alkylation products 15 and 28a-c were converted into optically active alpha-methylene-gamma-lactone and alpha-methylene macrolide derivatives. The high stereoselectivity demonstrated by the chiral phosphinocarboxylic acid-palladium catalyzed allylic alkylation suggested to be caused by an electronic repulsion between the carboxy group on the ligand and the incoming soft carbon nucleophile, which directs the nucleophilic attack on one of the pi-allyl carbons.

  DOI：

  10.1016/s0957-4166(00)86121-2
• 作为产物：
  描述：

  cyclopentanone (2,4,6-triisopropylbenzenesulfonyl)hydrazone 在 双氧水 、 仲丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (1-cyclopentenyl)-diphenylphosphine oxide
  参考文献：
  名称：

  Enephosphinilation

  摘要：

  DOI：

  10.1016/s0040-4039(01)82996-8

文献信息

• Reaction of Olefins with Dimethyl(methylthio)sulfonium Salts in the Presence of Triphenylphosphine. Preparation of Vinylphosphonium Salts
  作者：Kentaro Okuma、Tetsufumi Koike、Shin-ichi Yamamoto、Hiroshi Takeuchi、Kazuki Yonekura、Masaaki Ono、Hiroshi Ohta

  DOI：10.1246/bcsj.65.2375

  日期：1992.9

  Olefins were effectively converted into the corresponding (2-methylthioalkyl)triphenylphosphonium salts by the reaction with dimethyl(methylthio)sulfonium salts in the presence of triphenylphosphine. 2-Triphenylphosphonioalkyldimethylsulfonium salts, synthesized by alkylation of the corresponding methylthiophosphonium salts, react with 1,8-diazabicyclo[5.4.0]undec-7-ene or aq NaOH to afford the corresponding

  通过在三苯基膦存在下与二甲基（甲硫基）锍盐反应，烯烃被有效地转化为相应的（2-甲硫基烷基）三苯基鏻盐。2-三苯基膦酰基烷基二甲基锍盐由相应的甲硫鏻盐烷基化合成，与 1,8-二氮杂双环 [5.4.0] 十一碳-7-烯或 NaOH 水溶液反应，以良好的收率得到相应的乙烯基鏻盐或乙烯基氧化膦。
• Copper‐Catalyzed C−P Cross‐Coupling of (Cyclo)alkenyl/Aryl Bromides and Secondary Phosphine Oxides with <i>in</i>   <i>situ</i> Halogen Exchange
  作者：Paweł Woźnicki、Marek Stankevič

  DOI：10.1002/ejoc.202100456

  日期：2021.6.25

  A protocol for copper-catalyzed halogen exchange/C−P cross-coupling between (cyclo)alkenyl/aryl bromides and secondary phosphine oxides has been developed. The addition of sodium iodide increases the yield of the cross-coupling by promoting in situ halogen exchange of organic bromides to the corresponding iodides.

  已经开发了用于（环）烯基/芳基溴化物和二级氧化膦之间的铜催化卤素交换/CP 交叉偶联的协议。碘化钠的添加通过促进有机溴化物与相应碘化物的原位卤素交换来增加交叉偶联的产率。
• Reaction of triphenylphosphine radical cation with cycloalkenes: electrochemical one-step preparation of 1-cycloalkenyltriphenylphosphonium salts
  作者：Hidenobu Ohmori、Toshikatsu Takanami、Masaichiro Masui

  DOI：10.1016/s0040-4039(00)98961-5

  日期：1985.1

  Constant current electrolysis of triphenylphosphine in dichloromethane at a graphite anode in the presence of cycloalkenes gave the corresponding 1-cycloalkenylphosphonium salts in reasonable yields.

  在存在环烯烃的情况下，在石墨阳极上，在二氯甲烷中用三氯甲烷在二氯甲烷中进行恒流电解，以合理的收率得到了相应的1-环烯基phosph盐。
• Okuma, Kentaro; Koike, Tetsufumi; Yamamoto, Shin-ichi, Chemistry Letters, 1989, p. 1953 - 1956
  作者：Okuma, Kentaro、Koike, Tetsufumi、Yamamoto, Shin-ichi、Yonekura, Kazuki、Ohta, Hiroshi

  DOI：——

  日期：——
• Haynes, Richard K.; Katsifis, Andrew G., Australian Journal of Chemistry, 1989, vol. 42, # 9, p. 1473 - 1484
  作者：Haynes, Richard K.、Katsifis, Andrew G.

  DOI：——

  日期：——