tris(1-naphthyl)stilbane | 27309-70-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tris(1-naphthyl)stilbane
• 英文别名: tris(1-naphthyl)stibine；tri-[1]naphthyl-stibine；Tri-[1]naphthyl-stibin；Tri-(naphthyl-(1))-antimon；Tri-α-naphthylstibin；tri-naphthyl-antimony
• CAS: 27309-70-2
• 化学式: C₃₀H₂₁Sb
• 分子量: 503.247
• InChiKey: FXMLATQFGNVJFQ-UHFFFAOYSA-N

物化性质

• 熔点：
  218 °C

计算性质

• 辛醇/水分配系数(LogP)：
  5.66
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

锑在人体内广泛分布。头发和皮肤含有最高的锑水平。肾上腺、肺、大肠、气管、小脑和肾脏也含有相对较高的锑。血液是将吸收的锑运输到身体各个组织隔室的主要载体。锑是一种金属，因此不会发生分解代谢。锑可以与巯基和磷酸共价相互作用，以及与许多内源性配体（例如，蛋白质）进行可逆的绑定相互作用。目前尚不清楚这些相互作用在毒理学上是否具有重要意义。锑通过尿液和粪便排出。部分粪便中的锑可能代表未被吸收的锑，这些锑通过粘液纤毛活动从肺部清除到食管，再进入胃肠道。（L741）

Antimony is widely distributed throughout the body. The hair and skin contain the highest levels of antimony. The adrenal glands, lung, large intestine, trachea, cerebellum, and kidneys also contain relatively high levels of antimony. Blood is the main vehicle for the transport of absorbed antimony to various tissue compartments of the body. Antimony is a metal and, therefore, does not undergo catabolism. Antimony can covalently interact with sulfhydryl groups and phosphate, as well as numerous reversible binding interactions with endogenous ligands (e.g., proteins). It is not known if these interactions are toxicologically significant. Antimony is excreted via the urine and feces. Some of the fecal antimony may represent unabsorbed antimony that is cleared from the lung via mucociliary action into the esophagus to the gastrointestinal tract. (L741)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

吸入数据表明心肌是锑中毒的目标。锑可能通过干扰糖原分解和糖异生途径的酶来影响循环中的葡萄糖。锑的作用机制尚不清楚。然而，一些研究表明，锑与巯基团结合，包括那些对组织呼吸重要的几种酶中的巯基团。BAL的解毒作用取决于其防止或打断锑与关键酶结合的能力。此外，死亡原因被认为与急性砷中毒基本相同。(T18, L741, A238)

The inhalation data suggests that the myocardium is a target of antimony toxicity. It is possible that antimony affects circulating glucose by interfering with enzymes of the glycogenolysis and gluconeogenesis pathways. The mechanism of action of antimony remains unclear. However, some studies suggest that antimony combines with sulfhydryl groups including those in several enzymes important for tissue respiration. The antidotal action of BAL depends on its ability to prevent or break the union between antimony and vital enzymes. Moreover, the The cause of death is believed to be essentially the same as that in acute arsenic poisoning. (T18, L741, A238)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

无致癌性迹象（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity (not listed by IARC). (L135)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

皮肤接触锑可以导致锑斑（围绕汗腺和皮脂腺的丘疹和脓疱）。锑中毒还可能导致肺尘埃沉着病。吸入锑可能导致肺部功能改变和其他影响，包括慢性支气管炎、慢性肺气肿、活动性肺结核、胸膜粘连和刺激。锑中毒还可能导致血压升高。心肌抑制、血管扩张和体液流失可能导致低血压、电解质紊乱和急性肾衰竭的休克。脑水肿、昏迷、抽搐和死亡也是可能的。（L741）

Dermal exposure to antimony can cause antimony spots (papules and pustules around sweat and sebaceous glands). Antimony poisoning can also lead to pneumoconiosis. Alterations in pulmonary function and other effects including chronic bronchitis, chronic emphysema, inactive tuberculosis, pleural adhesions, and irritation can result from inhalation of antimony. Increased blood pressure can also result from antimony poisoning. Myocardial depression, vasodilation and fluid loss may cause shock with hypotension, electrolyte disturbances and acute renal failure. Cerebral oedema, coma, convulsions, and death are possible. (L741)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

吸入（L741）；口服（L741）；皮肤给药（L741）

Inhalation (L741) ; oral (L741) ; dermal (L741)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

腹部疼痛、呕吐、腹泻可能是由吸入锑引起的。呼吸困难、头痛、呕吐、咳嗽、结膜炎和鼻出血脓性分泌物可能是由吸入暴露引起的。皮肤或眼睛接触可能会导致暴露表面疼痛和发红。（T64, L741）

Abdominal pain, vomiting, diarrhea can result from inhalation of antimony. Dyspnea, headache, vomiting,cough, conjunctivitis, and bloody purulent discharge from nose can result from inhalation exposure. Skin or eye contact can cause pain and redness of the exposed surface. (T64, L741)

来源:Toxin and Toxin Target Database (T3DB)

反应信息

• 作为反应物：
  描述：

  tris(1-naphthyl)stilbane 在 Br₂ 作用下， 以 not given 为溶剂， 生成 tri(α-naphthyl)antimony(III) dibromide
  参考文献：
  名称：

  合成，灭活放射化学及专有的芳基-芳基-烷基-香辛基等的衍生物衍生出卤素

  摘要：

  烷基或芳基卤化镁在三氯化锑上的直接缩合已用于合成标记的stibines。通过从相应的卤化物中萃取溶剂，可以以良好的收率获得三烷基三芳基或三芳基锑二氟化物。给出了通过放射化学标记获得的一些分配系数值。已经研究了这些化合物的水解。

  DOI：

  10.1016/s0022-328x(00)93683-0
• 作为产物：
  描述：

  三氯化锑 以 四氢呋喃 为溶剂， 以56%的产率得到tris(1-naphthyl)stilbane
  参考文献：
  名称：

  合成，灭活放射化学及专有的芳基-芳基-烷基-香辛基等的衍生物衍生出卤素

  摘要：

  烷基或芳基卤化镁在三氯化锑上的直接缩合已用于合成标记的stibines。通过从相应的卤化物中萃取溶剂，可以以良好的收率获得三烷基三芳基或三芳基锑二氟化物。给出了通过放射化学标记获得的一些分配系数值。已经研究了这些化合物的水解。

  DOI：

  10.1016/s0022-328x(00)93683-0

文献信息

• Synthesis of arylboronates by boron-induced ipso-deantimonation of triarylstibanes with boron trihalides and its application in one-pot two-step transmetallation/cross-coupling reactions
  作者：Shuji Yasuike、Kazuhide Nakata、Weiwei Qin、Mio Matsumura、Naoki Kakusawa、Jyoji Kurita

  DOI：10.1016/j.jorganchem.2015.04.017

  日期：2015.7

  The reaction of triarylstibanes (1) with boron trihalides (BCl3, and BBr3) afforded arylboron dihalides (2) by utilizing all the three aryl groups on the antimony. Boron intermediates (2) were transformed to arylboronates (3) in good to excellent yields by treatment with methanol and 1,3-propanediol. Further, the Pd-catalyzed reactions of 2 with organic halides such as 1-bromonaphthalene and benzoyl

  三芳基苯乙烯类化合物（1）与三卤化硼（BCl 3和BBr 3）的反应通过利用锑上的所有三个芳基基团提供了芳基硼二卤化物（2）。通过用甲醇和1，3-丙二醇处理，将硼中间体（2）以良好至优异的产率转化为芳基硼酸酯（3）。此外，在H 2 O存在下Pd催化2与有机卤化物（例如1-溴萘和苯甲酰氯）的反应提供了相应的交叉偶联产物，不对称联芳基（4）和酮（5），以中等到良好的产量。通过分子轨道计算确定三芳基苯乙烯类化合物（1）与BCl 3提供2的金属转移的势能面。对取代基对理论计算的反应性的影响的分析表明，环取代基对这些金属转移反应的共振作用的重要性。
• Palladium(II)-catalyzed hydroarylation of α,β-unsaturated aldehydes and ketones with triarylstibines in the presence of silver acetate
  作者：Chan Sik Cho、Koichiro Tanabe、Sakae Uemura

  DOI：10.1016/0040-4039(94)88042-5

  日期：1994.2

  Triarylstibines react with α,β-unsaturated aldehydes and ketones in acetic acid at 25°C in the presence of silver acetate and a catalytic amount of palladium(II) acetate to afford the hydroarylation products by conjugate addition in good yields.

  在乙酸银和催化量的乙酸钯（II）的存在下，在乙酸中，三芳基sti啶与α，β-不饱和醛和酮在乙酸中于25℃反应，以高收率通过共轭物加成提供加氢芳基化产物。
• A Novel Transmetallation of Triarylstibanes into Arylboronate: Boro-induced Ipso-deantimonation and Its Theoretical Calculation
  作者：Shuji Yasuike、Kazuhide Nakata、Weiwei Qin、Toshiyuki Kaji、Jyoji Kurita

  DOI：10.1246/cl.2006.1402

  日期：2006.12

  Treatment of triarylstibanes with boron trichloride followed by derivatization with methanol and 1,3-propanediol afforded arylboronates in good yield with all three aryl groups on the antimony being utilized. Theoretical calculation of the reaction pathway revealed that the transformation proceeds through boro-induced ipso-deantimonation and the reactivity of Ph3M (M = P, As, Sb, and Bi) should be governed by the stability of the corresponding cations Ar2M+.

  与三氯化硼反应后，对三芳基锑进行甲醇和1,3-丙二醇的衍生化，得到良产率的芳基硼酸酯，且锑上的三个芳基均被利用。理论计算反应途径揭示，该转化通过硼诱导的邻位去锑反应进行，而 Ph3M（M = P, As, Sb, Bi）的反应性应由相应阳离子 Ar2M+ 的稳定性主导。
• Palladium(II)-Catalyzed Conjugate Addition of Aromatics to<i>α</i>,<i>β</i>-Unsaturated Ketones and Aldehydes with Arylantimony Compounds
  作者：Chan Sik Cho、Shin-ichi Motofusa、Kouichi Ohe、Sakae Uemura

  DOI：10.1246/bcsj.69.2341

  日期：1996.8

  Triarylstibines react with α,β-unsaturated ketones and aldehydes in acetic acid at room temperature in the presence of AgOAc and a catalytic amount of Pd(OAc)2 to afford the conjugate addition products (the formal hydroarylated compounds to an olefinic part) in good yields. In contrast, diarylantimony chlorides, arylantimony dichlorides, and diphenylantimony acetate react with the enones and enals

  在室温下，在 AgOAc 和催化量的 Pd(OAc)2 存在下，三芳基锑与乙酸中的 α,β-不饱和酮和醛反应，以良好的方式提供共轭加成产物（正式的氢化芳基化合物到烯烃部分）产量。相比之下，二芳基锑氯化物、芳基二氯化锑和二苯基乙酸锑即使在没有 AgOAc 的情况下也能与烯酮和烯醛反应，与来自三芳基锑的产物相比，以更高的产率提供相同的产物。这些是使用芳基锑 (III) 化合物的新 C-C 键形成反应，其中提出了钯烯醇化物或三价锑烯醇化物的形成作为中间体。
• CIV.—The action of inorganic halides on organometallic compounds
  作者：Frederick Challenger、Freda Pritchard

  DOI：10.1039/ct9242500864

  日期：——