dibutylstannane | 1002-53-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机过渡后金属化合物
• 英文名称: dibutylstannane
• 英文别名: Dibutyl-stannan；Dibutylzinn-dihydrid；Di-n-butyl-zinndihydrid；Di-n-butyl-stannan；dibutyltin dihydride；di-n-butyltin dihydride
• CAS: 1002-53-5
• 化学式: C₈H₂₀Sn
• 分子量: 234.957
• InChiKey: WCRDXYSYPCEIAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  9
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

尽管锡金属的吸收非常差，但锡化合物可以通过口服、吸入或皮肤途径被吸收，有机锡化合物的吸收速度远比无机锡化合物快。锡可能进入血液并绑定到血红蛋白上，在体内分布并在肾脏、肝脏、肺和骨骼中积累。有机锡化合物可能在肝脏中通过细胞色素P-450酶催化发生脱烷基化、羟基化、脱芳香化和氧化。脱烷基化产生的烷基产物会与谷胱甘肽结合并进一步代谢成巯基尿酸衍生物。锡及其代谢物主要通过尿液和粪便排出体外。(L308)

Though tin metal is very poorly absorbed, tin compounds may be absorbed via oral, inhalation, or dermal routes, with organotin compounds being much more readily absorbed than inorganic tin compounds. Tin may enter the bloodstream and bind to hemoglobin, where it is distributed and accumulates mainly in the kidney, liver, lung, and bone. Organotin compounds may undergo dealkylation, hydroxylation, dearylation, and oxidation catalyzed by cytochrome P-450 enzymes in the liver. The alkyl products of dealkylation are conjugated with glutathione and further metabolized to mercapturic acid derivatives. Tin and its metabolites are excreted mainly in the urine and feces. (L308)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

有机锡化合物产生神经毒性和免疫毒性效应。有机锡可能直接激活胶质细胞，通过局部释放促炎细胞因子、肿瘤坏死因子-α和/或白细胞介素，从而促进神经细胞退化。它们还可能通过直接作用于神经细胞来诱导凋亡。有机锡化合物刺激脑组织中神经递质的释放和/或减少神经细胞对神经递质的摄取，包括天冬氨酸、GABA、谷氨酸、去甲肾上腺素和血清素。这可能是神经细胞丢失的一个促成因素或结果。有机锡的免疫毒性特征是由抑制未成熟胸腺细胞的增殖和成熟胸腺细胞的凋亡引起的胸腺萎缩。人们认为有机锡化合物通过抑制DNA和蛋白质合成、诱导参与凋亡的基因（如nur77）的表达以及破坏细胞内钙水平的调节来发挥这些作用，从而导致不受控制的活性氧种类的产生、细胞色素c释放到细胞质中以及凋亡的蛋白水解和核酸酶级联。未成熟胸腺细胞增殖的抑制进一步导致T细胞介导的免疫应答的抑制。有机锡也是内分泌干扰物，被认为通过不适当的受体激活导致脂肪细胞分化，从而促进肥胖。无机锡引发红细胞溶解，导致锡诱导的贫血。(L308, A182, A184)

Organotin compounds produce neurotoxic and immunotoxic effects. Organotins may directly activate glial cells contributing to neuronal cell degeneration by local release of pro-inflammatory cytokines, tumor necrosis factor-_, and/or interleukins. They may also induce apoptosis by direct action on neuronal cells. Organotin compounds stimulate the neuronal release of and/or decrease of neuronal cell uptake of neurotransmitters in brain tissue, including aspartate, GABA, glutamate, norepinephrine, and serotonin. This may be either a contributing factor to or result of the neuronal cell loss. The immunotoxic effects of organotins are characterized by thymic atrophy caused by the suppression of proliferation of immature thymocytes and apoptosis of mature thymocytes. Organotin compounds are believed to exert these effects by suppressing DNA and protein synthesis, inducing the expression of genes involved in apoptosis (such as nur77), and disrupting the regulation of intracellular calcium levels, giving rise to the uncontrolled production of reactive oxygen species, release of cytochrome c to the cytosol, and the proteolytic and nucleolytic cascade of apoptosis. The suppression of proliferation of immature thymocytes further results in the suppression of T-cell-mediated immune responses. Organotins are also endocrine disruptors and are believed to contribute to obesity by inappropriate receptor activation, leading to adipocyte differentiation. Inorganic tin triggers eryptosis, contributing to tin-induced anemia. (L308, A182, A184)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

吸入或吞咽有机锡，或者皮肤接触有机锡，可能会干扰大脑和神经系统的工作方式，严重情况下可能导致死亡。有机锡化合物还可能损害免疫和生殖系统。

Breathing or swallowing, or skin contact with organotins, can interfere with the way the brain and nervous system work, causing death in severe cases. Organic tin compounds may also damage the immune and reproductive system. (L307, L308)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（L308）；吸入（L308）；皮肤给药（L308）

Oral (L308) ; inhalation (L308) ; dermal (L308)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

无机或有机锡化合物放置在皮肤上或进入眼睛中可能会引起皮肤和眼睛的刺激。

Inorganic or organic tin compounds placed on the skin or in the eyes can produce skin and eye irritation. (L308)

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 海关编码：
  2931909090

反应信息

• 作为反应物：
  描述：

  dibutylstannane 以 四氢呋喃 、 甲基环己烷 为溶剂， 生成 二丁基二氯化锡
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sn: Org.Verb.3, 1.1.6.1.3, page 105 - 108

  摘要：

  DOI：
• 作为产物：
  描述：

  二丁基二氯化锡 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以78%的产率得到dibutylstannane
  参考文献：
  名称：

  交替聚锡锡烷：合成与性质

  摘要：

  在非极性溶剂中和温和的反应条件下，烷基或芳基锡二氢化物和锡二酰胺的无催化剂化学计量缩聚反应产生了交替的聚锡锡烷的第一个实例。

  DOI：

  10.1039/c5cc00568j
• 作为试剂：
  描述：

  反式肉桂醛 、 2,3-二甲基-1,3-丁二烯 在 甲醇 、 二苯基硅烷 、 二丁基二碘锡烷 、 dibutylstannane 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以36%的产率得到(E)-4,4,5-trimethyl-1-phenylhexa-1,5-dien-3-ol
  参考文献：
  名称：

  1,3-丁二烯与乙二醛氢化物催化的醛的无过渡金属还原偶联

  摘要：

  在这项研究中，开发了Bu 2 SnIH催化的1,3-二烯与醛的直接偶联。该反应可以适合于不使用过渡金属催化剂的偶联。许多类型的醛被用于该反应。MeOH的加入促进了催化循环。

  DOI：

  10.1021/acs.orglett.7b02671

文献信息

• Regio- and stereoselective hydrostannation of allenes using dibutyliodotin hydride (Bu2SnIH) and successive coupling with aromatic halides
  作者：Naoki Hayashi、Kazunao Kusano、Shingo Sekizawa、Ikuya Shibata、Makoto Yasuda、Akio Baba

  DOI：10.1039/b712998j

  日期：——

  Regio- and stereoselective hydrostannation of allenes by using di-n-butyliodotin hydride (Bu2SnIH) was accomplished to give α,β-disubstituted vinyltins, which induced the synthesis of multi-substituted alkenes in a one-pot procedure.

  利用二正丁基碘锡烷氢（Bu2SnIH）实现了烯丙体的区域和立体选择性氢锡化反应，得到了α,β-二取代的乙烯基锡化合物，进而通过一锅法合成多取代烯烃。
• Hydroindation of allenes and its application to radical cyclization
  作者：Naoki Hayashi、Yusuke Hirokawa、Ikuya Shibata、Makoto Yasuda、Akio Baba

  DOI：10.1039/b803314e

  日期：——

  Hydroindation of allenes and radical cyclization of 1,2,7-trienes (allenenes) were accomplished by HInCl2 with high regioselectivity to afford a variety of cyclic compounds. The resulting vinylic indiums could be used for successive coupling reactions in a one-pot procedure. The use of HInCl2 generated slowly in situ is extremely effective for the radical cyclization.

  所有烯的氢化及1,2,7-三烯（烯烯）的自由基环化可通过HInCl2以高区域选择性实现，从而获得多种环状化合物。生成的乙烯基铟可用于一锅法的连续偶联反应。使用缓慢原位生成的HInCl2对自由基环化极为有效。
• Tin-oxygen-phosphorus compounds
  作者：R.E. Ridenour、E.E. Flagg

  DOI：10.1016/s0022-328x(00)89764-8

  日期：1969.3

  consistent with 5-coordinate tin for triorganotin diorganophosphinates, (I); both 4- and 5-coordinate tin for bis(triorganotin) organophosphonates, (II); 5-coordinate tin for poly(diorganotin organophosphonates), (III); and 6-coordinate tin for diorganotin bis(diorganophosphinates), (IV). Structures are proposed on the basis of molecularity, infrared, NMR, and Mössbauer data.

  描述并表征了四种类型的锡-氧-磷化合物。所有的化合物都是低聚的，并结合有膦酰基或膦酰基桥接。物理数据与三有机锡二有机次膦酸酯的5坐标锡一致（I）；双（三有机锡）有机膦酸酯的4-和5-配位锡，（II）；聚（二有机锡有机膦酸酯）的5-配位锡，（III）；二有机锡双（二有机次膦酸酯）（IV）的6-配位锡。根据分子量，红外，NMR和Mössbauer数据提出了结构。
• Oligoribonucleotides and ribonucleases for cleaving RNA
  申请人：Isis Pharmaceuticals, Inc.

  公开号：US06107094A1

  公开（公告）日：2000-08-22

  Oligomeric compounds including oligoribonucleotides and oligoribonucleosides are provided that have subsequences of 2'-pentoribofuranosyl nucleosides that activate dsRNase. The oligoribonucleotides and oligoribonucleosides can include substituent groups for increasing binding affinity to complementary nucleic acid strand as well as substituent groups for increasing nuclease resistance. The oligomeric compounds are useful for diagnostics and other research purposes, for modulating the expression of a protein in organisms, and for the diagnosis, detection and treatment of other conditions susceptible to oligonucleotide therapeutics. Also included in the invention are mammalian ribonucleases, i.e., enzymes that degrade RNA, and substrates for such ribonucleases. Such a ribonuclease is referred to herein as a dsRNase, wherein "ds" indicates the RNase's specificity for certain double-stranded RNA substrates. The artificial substrates for the dsRNases described herein are useful in preparing affinity matrices for purifying mammalian ribonuclease as well as non-degradative RNA-binding proteins.

  提供了包括寡核苷酸和寡核苷在内的寡聚合物化合物，其具有激活双链RNA酶的2'-戊核糖核苷亚序列。这些寡核苷酸和寡核苷可以包括取代基团，用于增加与互补核酸链的结合亲和力，以及用于增加核酸酶抗性的取代基团。这些寡聚合物化合物对于诊断和其他研究目的、调节生物体中蛋白质表达以及对易受寡核苷酸治疗的其他疾病进行诊断、检测和治疗都是有用的。该发明还包括哺乳动物核酸酶，即降解RNA的酶，以及这些核酸酶的底物。这样的核酸酶在此处被称为双链RNA酶，其中“ds”表示RNase对特定双链RNA底物的特异性。此处描述的双链RNA酶的人工底物对于制备亲和基质以纯化哺乳动物核酸酶以及非降解RNA结合蛋白是有用的。
• New and efficient synthesis of solid-supported organotin reagents and their use in organic synthesis
  作者：Alejandro G. Hernán、Peter N. Horton、Michael B. Hursthouse、Jeremy D. Kilburn

  DOI：10.1016/j.jorganchem.2005.11.031

  日期：2006.4

  prepared, including for the first time resin-bound dimethyl tin reagents. Mild methodology has also been developed for the very efficient synthesis of resin-bound distannanes. The resin-bound tin chloride reagents have been used in a catalytic Stille coupling cycle and the resin-bound distannanes have been used in atom transfer cyclisations and proved to be much more effective than previously described

  已经制备了新型的与树脂结合的有机锡试剂，包括首次与树脂结合的二甲基锡试剂。还开发了温和的方法，以非常有效地合成树脂结合的二锡烷。与树脂结合的氯化锡试剂已用于催化斯蒂勒偶联循环中，并且与树脂结合的二锡烷已用于原子转移环化中，并被证明比以前描述的与树脂结合的二锡烷更有效。如所期望的，使用树脂结合的锡试剂有助于它们在反应结束时易于去除，因此有机产物中的残留锡水平较低或可忽略不计。但是，树脂结合的二锡烷不能成功地用于钯催化的简单芳基碘化物的锡烷基化反应，这将为芳香族底物的放射性标记提供有用的方法。锡烷基化过程失败的原因尚不清楚，但晶体结构证据表明，与树脂结合的锡原子与相邻的醚氧之间存在高价相互作用，这可能影响锡中间体在锡烷基化序列中的反应性。