3-trimethylsilylprop-2-ynyldiisobutyltelluronium bromide | 143798-87-2

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: 3-trimethylsilylprop-2-ynyldiisobutyltelluronium bromide
• 英文别名: Telluronium, bis(2-methylpropyl)[3-(trimethylsilyl)-2-propynyl]-, bromide；bis(2-methylpropyl)-(3-trimethylsilylprop-2-ynyl)tellanium;bromide
• CAS: 143798-87-2
• 化学式: Br*C₁₄H₂₉SiTe
• 分子量: 432.974
• InChiKey: UTFIJZZDGQKHKA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  对氟苯甲醛 、 3-trimethylsilylprop-2-ynyldiisobutyltelluronium bromide 在 正丁基锂 、 水 作用下， 生成 1-(4-fluorophenyl)-4-(trimethylsilyl)-3-butyn-1-ol
  参考文献：
  名称：

  Application of elementoorganic compounds of 15th and 16th Groups in organic synthesis. 100. Reactions of carbonyl compounds with [(trimethylsilyl)propargyl]diisobutyltelluronium bromide mediated by different strong bases: highly regioselective synthesis of (trimethylsilyl)propargyl alcohols and highly stereoselective synthesis of cis-(trimethylsilyl)alkynyl epoxides

  摘要：

  [(Trimethylsilyl)propargyl)]diisobutyltelluronium bromide (1), after being treated with alkyl- or aryllithium reagent, undergoes a lithium-tellurium exchange reaction via an unstable transient tetraorganyltellurium intermediate, and the in situ generated lithium species reacts with carbonyl compounds to give (trimethylsilyl)propargyl alcohols 2 in high yields with high regioselectivity. However, when the telluronium salt 1 was treated with nonnucleophilic bases such as LDA or lithium 2,2,6,6-tetramethylpiperidide, the moderately stabilized silylated telluronium ylide formed. The silylated telluronium ylide reacted with carbonyl compounds to afford (trimethylsilyl) alkynyl epoxides 11 in good to excellent yields with high cis stereoselectivity.

  DOI：

  10.1021/jo00050a042
• 作为产物：
  描述：

  3-溴-1-三甲基硅基-1-丙炔 、 di-isobutyl telluride 反应 4.0h， 以87%的产率得到3-trimethylsilylprop-2-ynyldiisobutyltelluronium bromide
  参考文献：
  名称：

  Application of elementoorganic compounds of 15th and 16th Groups in organic synthesis. 100. Reactions of carbonyl compounds with [(trimethylsilyl)propargyl]diisobutyltelluronium bromide mediated by different strong bases: highly regioselective synthesis of (trimethylsilyl)propargyl alcohols and highly stereoselective synthesis of cis-(trimethylsilyl)alkynyl epoxides

  摘要：

  [(Trimethylsilyl)propargyl)]diisobutyltelluronium bromide (1), after being treated with alkyl- or aryllithium reagent, undergoes a lithium-tellurium exchange reaction via an unstable transient tetraorganyltellurium intermediate, and the in situ generated lithium species reacts with carbonyl compounds to give (trimethylsilyl)propargyl alcohols 2 in high yields with high regioselectivity. However, when the telluronium salt 1 was treated with nonnucleophilic bases such as LDA or lithium 2,2,6,6-tetramethylpiperidide, the moderately stabilized silylated telluronium ylide formed. The silylated telluronium ylide reacted with carbonyl compounds to afford (trimethylsilyl) alkynyl epoxides 11 in good to excellent yields with high cis stereoselectivity.

  DOI：

  10.1021/jo00050a042

文献信息

• Highly stereoselective synthesis of vinyl and ethynylcyclopropane 1,1-dicarboxylic esters via semi-stabilized telluronium ylides
  作者：Yong Tang、Zheng-Fa Chi、Yao-Zeng Huang、Li-Xin Dai、Yi-Hua Yu

  DOI：10.1016/0040-4020(96)00427-9

  日期：1996.6

  ethynylcyclo-propane 1,1-dicarboxylic esters conveniently synthesized by the reaction of allylic diisobutyltelluronium ylides with alkylidene or arylmethy-lidene malonic esters with high yields and high stereoselectivity. The effects of the reaction media and bases used to produce the ylides on the stereoselectivity are studied.

  高度电子缺陷的乙烯基和乙炔基环丙烷1,1-二羧酸酯，可通过烯丙基二异丁基碲化钌与亚烷基或芳基甲基亚芳基丙二酸酯反应以高收率和高立体选择性方便地合成。研究了反应介质和用于制备酰化物的碱对立体选择性的影响。
• Facile and highly stereoselective synthesis of cis-trimethylsilylethynyl epoxides via a silylated telluronium ylide
  作者：Zhang-Lin Zhou、Yao-Zeng Huang、Li-Lan Shi

  DOI：10.1039/c39920000986

  日期：——

  Diisobutyltelluronium trimethylsilylpropynyl ylide, generated from 3-trimethylsilylprop-2-ynyldiisobutyltelluronium bromide with lithium 2,2,6,6-tetramethylpiperidide (LiTMP), reacts with carbonyl compounds to afford predominately cis-trimethylsilylethynyl epoxides in good to excellent yields.

  由3-三甲基甲硅烷基丙-2-炔基二异丁基碲化溴化锂与2,2,6,6-四甲基哌啶锂（LiTMP）生成的二异丁基碲铝三甲基甲硅烷基丙炔基内酯与羰基化合物反应生成主要为顺式-三甲基甲硅烷基乙炔基环氧化物，收率良好。
• Tellurium-Zinc exchange between organotelluronium salts and diethylzinc—reaction of the in situ generated mixed diorganozinc with carbonyl compounds
  作者：Wen-Hua Huang、Yao-Zeng Huang、Li-Xin Dai

  DOI：10.1016/s0040-4039(98)01443-9

  日期：1998.9

  Organotelluronium salts undergo a smooth tellurium-zinc exchange reaction with diethylzinc. The in situ generated mixed diorganozinc reagents reacted with carbonyl compounds to give secondary or tertiary alcohols in good to excellent yields, (C) 1998 Elsevier Science Ltd. All rights reserved.
• Application of elementoorganic compounds of 15th and 16th Groups in organic synthesis. 100. Reactions of carbonyl compounds with [(trimethylsilyl)propargyl]diisobutyltelluronium bromide mediated by different strong bases: highly regioselective synthesis of (trimethylsilyl)propargyl alcohols and highly stereoselective synthesis of cis-(trimethylsilyl)alkynyl epoxides
  作者：Zhanglin Zhou、Yaozeng Huang、Lilan Shi、Jiong Hu

  DOI：10.1021/jo00050a042

  日期：1992.11

  [(Trimethylsilyl)propargyl)]diisobutyltelluronium bromide (1), after being treated with alkyl- or aryllithium reagent, undergoes a lithium-tellurium exchange reaction via an unstable transient tetraorganyltellurium intermediate, and the in situ generated lithium species reacts with carbonyl compounds to give (trimethylsilyl)propargyl alcohols 2 in high yields with high regioselectivity. However, when the telluronium salt 1 was treated with nonnucleophilic bases such as LDA or lithium 2,2,6,6-tetramethylpiperidide, the moderately stabilized silylated telluronium ylide formed. The silylated telluronium ylide reacted with carbonyl compounds to afford (trimethylsilyl) alkynyl epoxides 11 in good to excellent yields with high cis stereoselectivity.