tris(4-methoxyphenyl)-l⁵-stibanediyl diacetate | 545379-80-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tris(4-methoxyphenyl)-l⁵-stibanediyl diacetate
• 英文别名: tris(p-anisyl)ylantimony diacetate；tris(p-anisyl)antimony diacetate；[(4-MeOC₆H₄)₃Sb(OAc)₂]
• CAS: 545379-80-4
• 化学式: C₂₅H₂₇O₇Sb
• 分子量: 561.235
• InChiKey: UCMQPWPYIPKDSF-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  联硼酸新戊二醇酯 、 tris(4-methoxyphenyl)-l⁵-stibanediyl diacetate 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 12.0h， 以89%的产率得到4-甲氧基苯硼酸新戊二醇酯
  参考文献：
  名称：

  Simple base-free Miyaura-type borylation of triarylantimony diacetates with tetra(alkoxo)diborons under aerobic conditions

  摘要：

  The reaction of triarylantimony diacetates with tetra(alkoxo)diborons in the presence of PdCl2(PPh3)(2) (1 mol%) catalyst resulted in the Miyaura-type B-arylation to form arylboronates in moderate to good yields under base-free conditions. In the present reaction, two of the three aryl groups of antimony reagent were transferred to the coupling products when the reaction was carried out under aerobic conditions, although only one of the three aryl group of the antimony reagent was involved under an argon atmosphere. The broad scope of the reaction was demonstrated by using a variety of triarylantimony diacetates with sterically hindered aryl groups and highly reactive p-bromo-functionalized aryl derivatives. (C) 2014 Published by Elsevier B.V.

  DOI：

  10.1016/j.jorganchem.2014.04.006
• 作为产物：
  描述：

  三(对茴香基)锑 、 溶剂黄146 在 叔丁基过氧化氢 作用下， 以 乙醚 为溶剂， 生成 tris(4-methoxyphenyl)-l⁵-stibanediyl diacetate
  参考文献：
  名称：

  五价三芳基锑二羧酸酯的Pd催化不饱和化合物的C-芳基化

  摘要：

  三芳基锑（V）衍生物Ar 3 SbX 2（X = Hal或酰氧基）是通过Ar 3 Sb与等摩尔量的过氧化物ROOH（R ​​= t- Bu，H）在酸或酸酐的存在下反应制得的。好到极好的产量。Ar 3 Sb（O 2 CR）2是钯在50°C的催化下，不饱和化合物（丙烯酸甲酯，苯乙烯，2-苯基丙烯和丙烯腈）的温和有效的C-芳基化试剂，PdCl 2是最有效的催化剂。Ar 3 SbHal 2在这些条件下不反应。

  DOI：

  10.1016/s0022-328x(02)02179-4

文献信息

• Triarylantimony dicarboxylates as pseudo-halides for palladium-catalyzed cross-coupling reaction with arylboronic acids and triarylbismuthanes without any base
  作者：Weiwei Qin、Shuji Yasuike、Naoki Kakusawa、Yoshiyuki Sugawara、Masatoshi Kawahata、Kentaro Yamaguchi、Jyoji Kurita

  DOI：10.1016/j.jorganchem.2007.10.030

  日期：2008.1

  diacetates (6) with organoboron reagents (9) in the presence of Pd(PPh3)4 led to the formation of cross-coupling products, biaryls (10, 12 and 14–17), in moderate to excellent yields under mild conditions without any base. Similar reaction of 6 with triarylbismuthanes (18) also gave the corresponding cross-coupling products. Single crystal X-ray analysis of tri(p-tolyl)antimony diacetate (6b) and tris(p-

  所述triarylantimony二乙酸酯的（反应6）与有机硼试剂（9中的Pd（PPh的存在下）3）4导致交叉耦合产物的形成，联芳基化合物（10，12和14 - 17，在中度至良好的产率）在没有任何碱的温和条件下。6与三芳基双muthanes（18）的相似反应也得到相应的交叉偶联产物。三（对甲苯基）二乙酸锑（6b）和三（对三氟甲基苯基）二乙酸锑（6e）的单晶X射线分析）揭示了两个中心锑原子的几何形状都介于三角形双锥体和五边形双锥体排列之间，并且锑和两个具有顺式取向的羰基氧原子之间存在分子内配位。
• Pd-Catalyzed P-Arylation of Triarylantimony Dicarboxylates with Dialkyl H-Phosphites without a Base: Synthesis of Arylphosphonates
  作者：Mio Matsumura、Yuqiang Dong、Naoki Kakusawa、Shuji Yasuike

  DOI：10.1248/cpb.c14-00727

  日期：——

  The reaction of triarylantimony diacetates [Ar3Sb(OAc)2] with dialkyl H-phosphites [H-PO(OR)2] in the presence of a Pd(PPh3)4 (5 mol%) catalyst led to the formation of arylphosphonates in moderate to excellent yield under base-free conditions. This reaction is the first example of carbon–phosphorus bond formation by using an organoantimony compound as a pseudo-halide.

  三芳基锑二乙酸酯[Ar3Sb(OAc)2]与二烷基次膦酸酯[H-PO(OR)2]在Pd(PPh3)4（5摩尔%）催化剂存在下进行反应，无需添加碱即可中等至极好产率地生成芳基膦酸酯。这种反应是首次利用有机锑化合物作为假卤化物的碳磷键形成实例。
• Palladium-catalyzed carbonylative cross-coupling reaction of triarylantimony dicarboxylates with arylboronic acids: Synthesis of biaryl ketones
  作者：Weiwei Qin、Shuji Yasuike、Naoki Kakusawa、Jyoji Kurita

  DOI：10.1016/j.jorganchem.2008.05.039

  日期：2008.8

  A novel palladium-catalyzed three- component carbonylative coupling reaction by use of triarylantimony diacetate, arylboronic acid and carbon monoxide ( 1 atm) could be attained under mild reaction conditions without any base as an additive. The reaction can be applied to a wide range of triarylantimony diacetates and boronic acids to afford the corresponding unsymmetrical biaryl ketones in good yields. (c) 2008 Elsevier B. V. All rights reserved.
• Copper- and base-free Sonogashira-type cross-coupling reaction of triarylantimony dicarboxylates with terminal alkynes under an aerobic condition
  作者：Xuan Wang、Weiwei Qin、Naoki Kakusawa、Shuji Yasuike、Jyoji Kurita

  DOI：10.1016/j.tetlet.2009.08.113

  日期：2009.11

  A simple copper- and base-free palladium-catalyzed Sonogashira-type cross-coupling by the use of triarylantimony dicarboxylates is described. Reaction of triarylantimony diacetates with terminal alkynes in the presence of 1 mol% of PdCl2(PPh3)(2) Catalyst led to the formation of cross-coupling products in good to excellent yields. The reaction proceeded effectively under an aerobic condition, in that two of the three aryl groups on antimony could be transferred to the coupling products, whereas only one of them was involved in the reaction in an argon atmosphere. The reaction is sensitive to the electronic nature of the diacetates, and those bearing an electron-withdrawing group on the aromatic ring showed higher reactivity than those having an electron-donating group. (C) 2009 Elsevier Ltd. All rights reserved.