Tributyl-(2-isopropyl-5-methyl-cyclohexyloxymethyl)-stannane | 148915-55-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Tributyl-(2-isopropyl-5-methyl-cyclohexyloxymethyl)-stannane
• 英文别名: Tributyl-[(5-methyl-2-propan-2-ylcyclohexyl)oxymethyl]stannane
• CAS: 148915-55-3
• 化学式: C₂₃H₄₈OSn
• 分子量: 459.344
• InChiKey: CBDVTALPZCGZHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.85
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Tributyl-(2-isopropyl-5-methyl-cyclohexyloxymethyl)-stannane 在 4 A molecular sieve 、 tetrabutylammonium tetrafluoroborate 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 menthyloxymethyl nitrile
  参考文献：
  名称：

  Selective formation of isonitriles by anodic oxidation of α-heteroatom-substituted organotin compounds

  摘要：

  在 Bu4NBF4âTHF 中对δ-杂原子取代的有机锡化合物进行阳极氧化，会导致碳锡键断裂，并完全生成异腈，而在 Bu4NClO4âCH2Cl2 中的反应则完全生成相应的腈。

  DOI：

  10.1039/c39940000549

文献信息

• Electrooxidative coupling of α-heteroatom-substituted organostannanes and organosilanes
  作者：Jun-ichi Yoshida、Masanori Itoh、Sachihiko Isoe

  DOI：10.1039/c39930000547

  日期：——

  Anodic oxidation of α-heteroatom-substituted organostannanes in the presence of organosilanes such as allylsilanes and silyl enol ethers results in the facile cleavage of the carbon–tin bond and introduction of allyl and acyl groups onto the carbon, respectively.

  在存在如烯丙基硅烷和硅醇醚等有机硅化合物的情况下，对α-杂原子取代的有机锡化合物进行阳极氧化，会促进碳-锡键的轻松断裂，并分别将烯丙基和酰基引入碳上。
• Electrochemical oxidation of α-alkoxystannanes
  作者：Jun-ichi Yoshida、Yuji Ishichi、Keiji Nishiwaki、Satoshi Shiozawa、Sachichiko Isoe

  DOI：10.1016/s0040-4039(00)92254-8

  日期：1992.4

  The introduction of tin on the carbon adjacent to the oxygen of aliphatic ethers results in significant decrease in the oxidation potentials. The effect of tin is much larger than that observed for silicon. Preparative electrochemical oxidation of alpha-alkoxystannanes results in selective cleavage of the carbon-tin bond and introduction of a nucleophile such as an alcohol onto the carbon.
• Redox selective reactions of organo-silicon and -tin compounds
  作者：Jun-ichi Yoshida、Keiji Nishiwaki

  DOI：10.1039/a803343i

  日期：——

  The C-Si and C-Sn sigma orbitals are higher in energy than C-H or C-C sigma orbitals, and therefore can interact with neighboring pi systems, non-bonding orbitals of heteroatoms, and other sigma systems such as those of C-Si and C-Sn, Such interactions cause an increase of the HOMO level which in turn favors electron transfer. On the basis of this effect various types of redox selective reactions of organo-silicon and -tin compounds have been developed.
• Selective formation of isonitriles by anodic oxidation of α-heteroatom-substituted organotin compounds
  作者：Jun-ichi Yoshida、Masanori Itoh、Yuko Morita、Sachihiko Isoe

  DOI：10.1039/c39940000549

  日期：——

  Anodic oxidation of α-heteroatom-substituted organotin compounds in Bu4NBF4–THF results in the cleavage of the carbon–tin bond and exclusive formation of isonitriles whereas the reaction in Bu4NClO4–CH2Cl2 gives rise to exclusive formation of the corresponding nitriles.

  在 Bu4NBF4âTHF 中对δ-杂原子取代的有机锡化合物进行阳极氧化，会导致碳锡键断裂，并完全生成异腈，而在 Bu4NClO4âCH2Cl2 中的反应则完全生成相应的腈。