四苯基锑乙酸盐 | 24696-71-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 四苯基锑乙酸盐
• 英文名称: triphenylstibonium acetate
• 英文别名: tetraphenylacetatoantimony(V)；tetraphenylantimony acetate；Ph4SbOAc；Tetraphenylstibanium;acetate
• CAS: 24696-71-7
• 化学式: C₂₆H₂₃O₂Sb
• 分子量: 489.217
• InChiKey: MOQVJYRFLPHSMW-UHFFFAOYSA-M

物化性质

• 熔点：
  120-133 °C(lit.)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn,N
• 安全说明：
  S61
• 危险类别码：
  R20/22,R51/53
• 危险品运输编号：
  UN 3077 9/PG 3
• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  四苯基锑乙酸盐 、 苄胺 在 copper diacetate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以71%的产率得到苯甲基苯胺
  参考文献：
  名称：

  Pentavalent Organoantimony Compounds as Mild N-Arylating Agents for Amines: Cu-Mediated Ullmann-Type N-Arylation with Tetraarylantimony(V) Acetates

  摘要：

  介绍了利用醋酸四芳基锑（Ar4SbOAc）对各种胺进行简单温和的铜介导芳基化反应。在醋酸铜（II）存在下，Ar4SbOAc 与脂肪族和富电子芳香族胺的乌尔曼型缩合反应进行得非常有效。芳基化反应可在有氧条件下进行，无需外源氧气。这种简单的方法超过了通常需要苛刻反应条件的传统乌尔曼缩合法。

  DOI：

  10.1248/cpb.57.436
• 作为产物：
  描述：

  tetraphenylacetatoantimony(V) crystal solvate with AcOH 以 solid 为溶剂， 生成 四苯基锑乙酸盐
  参考文献：
  名称：

  摘要：

  Catalytic C-phenylation of methyl acrylate to methyl cinnamate with the Ph4SbX complexes (X = F, Cl, Br, OH, OAc, O2CEt) in the presence of the palladium compounds PdCl2, Pd(OAc)(2), Pd-2(dba)(3), Pd(Ph3P)(2)Cl-2, and Pd(dppf)Cl-2 (dba is dibenzylideneacetone and dppf is bis(diphenylphosphinoferrocene)) was studied in organic solvents (MeCN, THF, DMF, MeOH, and AcOH). The highest yield of methyl cinnamate (73% based on the starting organometallic compound) was obtained for the Ph4SbCl-PdCl2 (1 : 0.04) system in acetonitrile.

  DOI：

  10.1023/a:1024883328867

文献信息

• Aminolysis of Triphenylantimony Dicarboxylates and Its Application to Catalytic Amidation
  作者：Ryoki Nomura、Takao Wada、Yasuhiro Yamada、Haruo Matsuda

  DOI：10.1246/cl.1986.1901

  日期：1986.11.5

  Triphenylantimony dicarboxylates (Ph3Sb(O2CR)2, where R=Me, CF3, Ph and CH2NH-Z) readily reacted with amines (R′NH2, where R′=n-C6H13, s-Bu, C6H11, and Ph) to afford corresponding amides and triphenylstibine oxide in fairly good yields. The amidation of RCO2H with R′NH2 was also catalyzed by the orgnoantimony compounds.

  三苯基锑二羧酸盐（Ph3Sb(O2CR)2，其中 R=Me、CF3、Ph 和 CH2NH-Z）容易与胺（R'NH2，其中 R'=n-C6H13、s-Bu、C6H11 和 Ph）反应得到相应的酰胺和三苯基氧化锑，收率相当好。RCO2H与R'NH2的酰胺化也由有机锑化合物催化。
• Palladium-Catalyzed C–H Arylation of Benzofurans with Triarylantimony Difluorides for the Synthesis of 2-Arylbenzofurans
  作者：Yuki Kitamura、Yuki Murata、Mizuki Iwai、Mio Matsumura、Shuji Yasuike

  DOI：10.3390/molecules26010097

  日期：——

  substances. Herein, the reaction of triarylantimony difluorides with benzofurans under aerobic conditions in 1,2-DCE, using 5 mol% Pd (OAc)2 and 2 eq. of CuCl2 at 80 °C, produced a variety of 2-arylbenzofurans in moderate-to-high yields. The reaction is sensitive to the electronic nature of the substituents on the benzene ring of the triarylantimony difluorides: an electron-donating group showed higher reactivity

  Pd 催化的区域选择性 C-H 芳基化是芳香杂环化学修饰的有用工具，2-芳基苯并呋喃衍生物作为生物活性物质受到关注。本文中，使用 5 mol% Pd (OAc)2 和 2 eq.，在 1,2-DCE 中的有氧条件下，三芳基锑二氟化物与苯并呋喃的反应。 CuCl2 在 80 °C 下生成多种 2-芳基苯并呋喃，产率中等至较高。该反应对三芳基二氟化锑苯环上取代基的电子性质敏感：给电子基团比吸电子基团表现出更高的反应性。三(对甲基苯基)二氟化锑的单晶X射线分析表明，中心锑原子呈现三角双锥几何形状。
• Raj, Prem; Rastogi, Rajiv, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1987, vol. 26, # 8, p. 679 - 681
  作者：Raj, Prem、Rastogi, Rajiv

  DOI：——

  日期：——
• Adducts of tetraphenylstibium nitrate with nitric acid and of tetraphenylstibium acetate with acetic acid: Syntheses and structures
  作者：V. V. Sharutin、V. S. Senchurin、O. K. Sharutina、L. P. Panova

  DOI：10.1134/s0036023608070206

  日期：2008.7

  The reactions of tetraphenylstibium nitrate with nitric acid and of tetraphenylstibium acetate with acetic acid yield adducts Ph4SbONO2 center dot HNO3 (I) and Ph4SbOC(O)CH3 center dot CHH3COOH (II). According to X-ray diffraction data, the antimony atom in [Ph4Sb](+)[O2N-O center dot center dot center dot H center dot center dot center dot O-NO2](-) has a tetrahedral coordination. The CSbC bond angles and Sb-C bond lengths vary within 108.04(6)degrees-109.75(4)angstrom and 2.096(1)-2.098(1) angstrom, respectively. The anion includes the intermolecular hydrogen bond O(1)-H(1)center dot center dot center dot O(1)'' the O(1)-H(1), H(1)center dot center dot center dot O(1)'', and O(1)center dot center dot center dot O(1)'' distances are 0.91(4), 1.56(4), and 2.460(2) angstrom, respectively; and the OHO angle is 169(5)angstrom. The nitrate groups are usually planar. Complex II also contains the intermolecular hydrogen bond with the following parameters: O(3)-H(3), 0.92 angstrom; H(3)center dot center dot center dot O(2), 1.68 angstrom; and O(3)center dot center dot center dot O(2) 2.594 angstrom; the O(2)H(3)O(3) angle is 172.1 angstrom. This H-bond noticeable changes the coordination polyhedron of the antimony atom compared to that in tetraphenylstibium acetate.
• Bone, Stephen P.; Sowerby, D. Bryan, Phosphorus, Sulfur and Silicon and the Related Elements, 1989, vol. 45, p. 23 - 30
  作者：Bone, Stephen P.、Sowerby, D. Bryan

  DOI：——

  日期：——