triphenylbismuth(V) dipropionate | 61174-97-8

• 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: triphenylbismuth(V) dipropionate
• 英文别名: triphenylbismuth dipropionate；Ph3Bi(O2CEt)2；triphenyl-di(propanoyloxy)bismuth
• CAS: 61174-97-8；153380-10-0
• 化学式: C₂₄H₂₅BiO₄
• 分子量: 586.441
• InChiKey: XNHILSAAGFEORC-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  丙烯酸甲酯（MA） 、 triphenylbismuth(V) dipropionate 在 palladium diacetate 、 氧气 作用下， 以 乙腈 为溶剂， 反应 14.0h， 生成 联苯 、 肉桂酸甲酯
  参考文献：
  名称：

  摘要：

  The C-phenylation of methyl acrylate to methyl cynnamate with Ph3Sb, Ph3SbX2 (X = Cl, OAc), Ph3Bi, and Ph3BiX2 (X = OAc, O2CEt) in the presence of PdCl2, Pd(OAc)(2), Li2PdCl4, NaPd(OAc)Cl-2, and Na2Pd(OAc)(2)Cl-2 was studied to show that the reactions with Ph3Sb and Ph3Sb(OAc)(2) are more selective and give higher yields of the target product than those with Ph3Bi and Ph3Bi(OAc)(2), while Ph3M(OAc)(2) are preferred over Ph3M. Copper(II) alkanecarboxylate additives have no effect on the yield of methyl cynnamate in the reactions with Ph3Sb.

  DOI：

  10.1023/a:1023335617165
• 作为产物：
  描述：

  三苯基铋 、 丙酸 在 叔丁基过氧化氢 作用下， 以 乙醚 为溶剂， 以80%的产率得到triphenylbismuth(V) dipropionate
  参考文献：
  名称：

  Study of homo- and cross-coupling competition in the reaction of triarylbismuth(V) dicarboxylates with methyl acrylate in the presence of a palladium catalyst

  摘要：

  Triarylbismuth(V) derivatives Ar3Bi(O2CR)(2) (Ar = Ph, m-Tol, p-Tol; R = H, Me, Et, n-Bu, t-Bu, n-C5H11, CF3, CH2Cl, CCl3, Ph) were prepared in good to excellent yields by reaction of Ar3Bi with equimolar amounts of t-BuOOH in the presence of an acid. These compounds were tested in the C-arylation reaction of methyl acrylate, as a model substrate, in the presence of palladium catalyst (4 mol%). It was found that triphenylbismuth dicarboxylates are very active phenylating agents under mild conditions (20 degrees C). The effect of the carboxylic group, the effect of the nature of the palladium catalyst and the effect of oxygen on the reactivity of the organobismuth compounds and on the selectivity of the C-arylation reaction were studied. Methyl cinnamate, the C-phenylation product, and biphenyl, the homo-coupling by-product, were obtained in all cases. Triphenylbismuth divalerate Ph3Bi(O2CBu)(2) is the most reactive compound among the triphenylbismuth dicarboxylates studied. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.04.051

文献信息

• Dephenylation of triphenylbismuth(v) and antimony(v) derivatives in a methyl acrylate—methanol system in the presence of copper and palladium salts
  作者：A. V. Gushchin、M. V. Korotkova、Yu. B. Malysheva、V. A. Morugova、D. V. Moiseev

  DOI：10.1007/s11172-006-0312-1

  日期：2006.4

  The influence of the central metal atom and acid residue in a molecule of organometallic compound Ph3MX2 (M = Bi, Sb; X = Cl, Br, OAc, O2CEt) on the direction and yield of dephenylation products in a methyl acrylate— methanol system in the presence of Cu(OAc)2 and Na2PdCl2(OAc)2 was studied at 50 °C in acetonitrile. The main product of dephenylation of the antimony compounds is methyl cinnamate (yield 0.31–1.59 moles per mole of the starting Ph3SbX2), while anisole (0.55–0.97 mol) and halobenzene (0.67–1.04 mol) are those for compounds Ph3Bi(O2CR)2 and Ph3BiHal2, respectively.

  研究了有机金属化合物 Ph3MX2（M = Bi、Sb；X = Cl、Br、OAc、O2CEt）分子中的中心金属原子和酸残基对丙烯酸甲酯-甲醇体系中在 Cu(OAc)2 和 Na2PdCl2(OAc)2 存在下于 50 °C、乙腈中的脱苯产物的方向和产率的影响。锑化合物的主要脱苯乙烯产物是肉桂酸甲酯（每摩尔起始 Ph3SbX2 的产率为 0.31-1.59 摩尔），而 Ph3Bi(O2CR)2 和 Ph3BiHal2 化合物的主要脱苯乙烯产物分别是苯甲醚（0.55-0.97 摩尔）和卤苯（0.67-1.04 摩尔）。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Bi: Org.Verb., 1.3.1.2.8.1, page 38 - 40
  作者：

  DOI：——

  日期：——
• Suzuki, Hitomi; Ikegami, Tohru; Matano, Yoshihiro, Journal of the Chemical Society. Perkin transactions I, 1993, # 20, p. 2411 - 2416
  作者：Suzuki, Hitomi、Ikegami, Tohru、Matano, Yoshihiro、Azuma, Nagao

  DOI：——

  日期：——
• 13C-nuclear magnetic resonance of some triaryl- and tri-alkylantimony and -bismuth derivatives
  作者：Akira Ouchi、Takashi Uehiro、Yukichi Yoshino

  DOI：10.1016/0022-1902(75)80751-2

  日期：1975.11
• DODONOV, V. A.;GUSHCHIN, A. V.;EZHOVA, M. B., ZH. OBSHCH. XIMII, 58,(1988) N 9, S. 2170-2171
  作者：DODONOV, V. A.、GUSHCHIN, A. V.、EZHOVA, M. B.

  DOI：——

  日期：——