(1-cyclobutenyl)triphenylphosphonium perchlorate | 86046-73-3

• 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: (1-cyclobutenyl)triphenylphosphonium perchlorate
• 英文别名: Cyclobuten-1-yl(triphenyl)phosphanium;perchlorate；cyclobuten-1-yl(triphenyl)phosphanium;perchlorate
• CAS: 86046-73-3
• 化学式: C₂₂H₂₀P*ClO₄
• 分子量: 414.825
• InChiKey: QZIZPZXDXYZRPU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1-cyclobutenyl)triphenylphosphonium perchlorate 在 sodium hydroxide 、 potassium permanganate 、 正丁基锂 、 ammonium cerium(IV) nitrate 、 硫酸 、 三氯硅烷 作用下， 以 水 、 丙酮 、 苯 为溶剂， 反应 25.0h， 生成 methyl trans-(2-diphenylphosphino)cyclobutanecarboxylate
  参考文献：
  名称：

  手性膦基羧酸配体，反式-2-（二苯基膦基）环烷烃羧酸的首次合成。膦-钯配合物催化不对称烯丙基烷基化

  摘要：

  首次合成的手性膦基羧酸有效地用作配位体，用于钯催化的3-乙酰氧基-1,3-二苯基-1-丙烯和2-环己烯基乙酸酯的不对称烯丙基烷基化反应，由丙二酸二甲酯或膦酸三乙酯和氢化钠形成的软碳负离子。烷基化产物的ee最高可达83％。

  DOI：

  10.1016/s0040-4039(00)97502-6
• 作为产物：
  描述：

  cyclobutyltriphenylphosphonium ylide 在 silver perchlorate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (1-cyclobutenyl)triphenylphosphonium perchlorate
  参考文献：
  名称：

  Synthesis and reactions of the (1-cyclobutenyl)triphenylphosphonium salt

  摘要：

  DOI：

  10.1021/jo00163a029

文献信息

• A new synthesis of 1,2-bisylidenecylobutanes and their application to the construction of polycyclic ring systems via sequential Diels–Alder reactions
  作者：Toru Minami、Yuki Taniguchi、Ichiro Hirao

  DOI：10.1039/c39840001046

  日期：——

  , conveniently synthesized from the (cyclobut-1-enyl)triphenylphosphonium salt, diethyl lithiophosphonate, and aromatic aldehydes, readily undergo sequential Diels–Alder reactions with dienophiles to give good yields of polycyclic compounds.

  由（环丁-1-烯基）三苯基phosph盐，二乙基硫代膦酸酯和芳香族醛方便地合成的1,2-双亚芳基环丁烷很容易与亲二烯体进行连续的Diels-Alder反应，从而获得良好的多环化合物收率。
• Synthesis of heterocyclic compounds containing phosphorus residues by cycloaddition of 1,3-dipoles to cyclobutenylphosphorus compounds
  作者：Toru Minami、Takeshi Hanamoto、Ichiro Hirao

  DOI：10.1021/jo00208a024

  日期：1985.4
• A new synthesis of cyclobutane annelated compounds by the use of a (1-cyclobutenyl)triphenylphosphonium salt
  作者：Yoshiharu Okada、Toru Minami、Shigenori Yahiro、Keiichi Akinaga

  DOI：10.1021/jo00265a047

  日期：1989.2
• Synthetic applications of the 1-cyclobutenyltriphenylphosphonium salt. Synthesis and reactions of 1,2-difunctionalized cyclobutanes
  作者：Toru Minami、Nobuo Harui、Yuki Taniguchi

  DOI：10.1021/jo00369a003

  日期：1986.9
• Synthesis of a novel type of chiral phosphinocarboxylic acids. The phosphine-palladium complexes catalyzed asymmetric allylic alkylation
  作者：Yoshiharu Okada、Toru Minami、Yasuo Umezu、Shinji Nishikawa、Ryoji Mori、Yutaka Nakayama

  DOI：10.1016/s0957-4166(00)86121-2

  日期：1991.1

  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.