3-trimethylsilylprop-2-enyldiisobutyltelluronium bromide | 147455-74-1

• 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-enyldiisobutyltelluronium bromide
• 英文别名: bis(2-methylpropyl)-[(E)-3-trimethylsilylprop-2-enyl]tellanium;bromide
• CAS: 147455-74-1
• 化学式: Br*C₁₄H₃₁SiTe
• 分子量: 434.99
• InChiKey: HHFYSCKDLYTREG-HRNDJLQDSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  17
• 可旋转键数：
  7
• 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：

  3-trimethylsilylprop-2-enyldiisobutyltelluronium bromide 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.33h， 生成 (2Z,5Z)-methyl-cis-4-phenyl-cis-7-(trimethylsilyl)cyclohepta-2,5-dienecarboxylate
  参考文献：
  名称：

  The Michael Addition−Elimination of Ylides to α,β-Unsaturated Imines. Highly Stereoselective Synthesis of Vinylcyclopropanecarbaldehydes and Vinylcyclopropylaziridines

  摘要：

  The Michael addition-elimination of ylide to alpha,beta-unsaturated imines leads to a highly diastereoselective and enantioselective synthesis of vinylcyclopropanecarbaldehydes in good to high yields for the first time. A sequential cyclopropanation-aziridination protocol for the preparation of cyclopropylaziridines is also developed with good diastereoselectivity in good to high yields.

  DOI：

  10.1021/ja052228y
• 作为产物：
  描述：

  反-3-(三甲基硅基)烯丙醇 在 三溴化磷 作用下， 生成 3-trimethylsilylprop-2-enyldiisobutyltelluronium bromide
  参考文献：
  名称：

  甲硅烷基化的碲化烯丙基内酯方便，立体选择性地合成三甲基甲硅烷基乙烯基氧杂环戊烷

  摘要：

  三甲基甲硅烷diisobutyltelluronium allylide，适度稳定的碲叶立德，从3-三甲基硅烷基-2- propenyldiisobutyltelluronium溴（生成3与LiTMP）中，用羰基化合物反应，得到环氧乙烷trimethylsilylvinyl在具有高优异的产率顺式立体选择性。

  DOI：

  10.1016/0040-4039(92)89042-b

文献信息

• A facile reaction of imines with telluronium allylide. Highly stereoselective synthesis of vinylaziridinesElectronic supplementary information (ESI) available: experimental section. See http://www.rsc.org/suppdata/cc/b4/b400464g/
  作者：Wei-Wei Liao、Xian-Ming Deng、Yong Tang

  DOI：10.1039/b400464g

  日期：——

  The reaction of telluronium allylides with alkylimines, generated in situ from alpha-amidoalkyl sulfones, affords cis-alkylvinylarizidines with good stereoselectivity in good yields. However, the same ylides react with N-aryl imines to provide trans-vinylaziridines.

  从α-酰胺基烷基砜原位产生的碲化烯丙基烯丙基烯化物与烷基亚胺的反应以良好的收率提供了具有良好的立体选择性的顺式-烷基乙烯基芳基叠氮烷。然而，相同的酰基化物与N-芳基亚胺反应以提供反式乙烯基氮丙啶。
• Highly Diastereoselective Synthesis of Vinylcyclopropane Derivatives with (−)-8-Phenylmenthol as Chiral Auxiliary
  作者：Song Ye、Yong Tang、Li-Xin Dai

  DOI：10.1021/jo010121x

  日期：2001.8.1

  telluronium allylide 4, generated in situ from the corresponding telluronium salt in the presence of LiTMP, reacted with (-)-8-phenylmenthyl alpha,beta-unsaturated esters to afford trans-2-silylvinyl-trans-3-substituted cyclopropyl esters with high diastereoselectivity in high yields. The absolute configuration was determined by chemical transformation. A mechanistic rationale is proposed.

  在LiTMP存在下由相应的碲盐原位生成的甲硅烷基碲化烯丙基内酯4与（-）-8-苯基薄荷基α，β-不饱和酯反应生成反式-2-甲硅烷基乙烯基-反式-3-取代的环丙基酯具有高非对映选择性和高收率。绝对构型通过化学转化确定。提出了机械原理。
• Telluronium Salts Mediated Aziridination of Chiral <i>N</i>-<i>tert</i>-Butylsulfinylimines:  Highly Stereoselective Synthesis of Optically Active Vinylaziridines
  作者：Jun-Cheng Zheng、Wei-Wei Liao、Xiao-Xia Sun、Xiu-Li Sun、Yong Tang、Li-Xin Dai、Jin-Geng Deng

  DOI：10.1021/ol051921n

  日期：2005.12.1

  [reaction: see text] Optically active cis-2-substituted vinylaziridines are synthesized by the reaction of N-tert-butylsulfinylimines with telluronium ylides with excellent diastereoselectivity in good to excellent yields.

  [反应：见正文]光学活性的顺式2-取代的乙烯基氮丙啶是通过N-叔丁基亚磺酰亚胺与碲化碲的反应而合成的，具有极好的非对映选择性，并具有良好的收率。
• Michael addition of silylated telluronium allylide to α,β-unsaturated esters: facile and stereoselective synthesis of trimethylsilylvinylcyclopropane derivatives
  作者：Yao-Zeng Huang、Yong Tang、Zhang-Lin Zhou、Ji-Ling Huang

  DOI：10.1039/c39930000007

  日期：——

  diisobutyltelluronium allylide, generated from 3-trimethylsilylprop-2-enyldiisobutyltelluronium bromide 1 with lithium 2,2,6,6-tetramethylpiperidide (LTMP), reacts with α,β-unsaturated esters to afford trimethylsilylvinylcyclopropane derivatives via Michael addition in excellent yields with high stereoselectivity.

  三甲基甲硅烷diisobutyltelluronium allylide，从3- trimethylsilylprop -2- enyldiisobutyltelluronium溴化物产生1与锂2,2,6,6-四甲基（LTMP）中，用α，β不饱和酯进行反应，得到trimethylsilylvinylcyclopropane衍生物经由迈克尔加成在具有高的产率优异立体选择性。
• Cyclopropanation Reactions of Allylic Ylides with α,β-Unsaturated Esters and Amides:  Tuning of Stereoselectivity and the Dramatic Effect of Lithium Salts
  作者：Yong Tang、Yao-Zeng Huang、Li-Xin Dai、Zheng-Fa Chi、Li-Ping Shi

  DOI：10.1021/jo960063t

  日期：1996.1.1

  The allylic telluronium ylides 2a-2c, generated in situ from the corresponding telluronium salts 1a-1c in the presence of a lithium salt, reacted with alpha,beta-unsaturated esters or amides to afford trans-2-vinyl-trans-3-substituted cyclopropyl esters or amides, respectively, with high selectivity and generally excellent yields. in the absence of lithium salts, the stereoselectivity of these reactions changed to give cis-2-vinyl-trans-3-substituted cyclopropyl esters or amides. The ratio of the two isomers 4 and 5 can be tuned from 99:1 to 1:99. Other factors, such as temperature, solvents, and amounts of base, are also shown to influence the stereochemistry of this reaction. mechanism for tuning of the reaction stereochemistry by simply varying reaction conditions is proposed.