3-(butyltellanyl)-5,5-dimethyl-cyclohex-2-enone | 849595-89-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(butyltellanyl)-5,5-dimethyl-cyclohex-2-enone
• 英文别名: 3-(butyltellanyl)-5,5-dimethylcyclohex-2-enone；3-Butyltellanyl-5,5-dimethylcyclohex-2-en-1-one
• CAS: 849595-89-7
• 化学式: C₁₂H₂₀OTe
• 分子量: 307.89
• InChiKey: WTHJXSJMRVTLEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(butyltellanyl)-5,5-dimethyl-cyclohex-2-enone 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 3-(butyltellanyl)-5,5-dimethylcyclohex-2-enol
  参考文献：
  名称：

  将β-丁基tellanylα，β-不饱和羰基化合物化学选择性还原为烯丙基醇

  摘要：

  （Z）-β-丁基tellanylα，β-不饱和羰基化合物是通过炔烃的加氢酯化反应或烯醇甲苯磺酸盐的加成/消除顺序立体产生的。用NaBH 4 / MeOH，NaBH 4 ·CeCl 3 ·7H 2 O / MeOH和DIBAL-H系统将β-丁基tellanyl-烯酮化学选择性还原为相应的烯丙醇，并保留Z立体化学。

  DOI：

  10.1016/j.tet.2005.06.090
• 作为产物：
  描述：

  正丁基锂 、 diethyl 5,5-dimethyl-3-oxocyclohex-1-enyl phosphate 在 碲化氢 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.33h， 以91%的产率得到3-(butyltellanyl)-5,5-dimethyl-cyclohex-2-enone
  参考文献：
  名称：

  Diastereoselective synthesis of α,β-unsaturated systems

  摘要：

  Functionalized Z-vinylic tellurides were used in substitution reactions with lower order cyanocuprates leading to alpha, beta-unsaturated ketones and esters in good yields. In the case of acyclic tellurides, the product was obtained in high diastereoselectivity. The control of the stereoselectivity was achieved by simple change of the reaction temperature. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.025

文献信息

• Novel cross-coupling reactions between organotellurides and Grignard reagents employing a MnCl2/CuI catalytic system
  作者：Marcio S. Silva、Renan S. Ferrarini、Bruno A. Sousa、Fabiano T. Toledo、João V. Comasseto、Rogério A. Gariani

  DOI：10.1016/j.tetlet.2012.04.134

  日期：2012.7

  We present a general protocol for the cross-coupling reaction of Grignard reagents and organic tellurides. Aryl Grignard reagents react stereospecifically with vinyl tellurides in the presence of a catalytic amount of manganese (II) chloride and copper (I) iodide to produce good yields of the corresponding cross-coupling products.

  我们提出了格氏试剂和有机碲化物交叉偶联反应的一般方案。在催化量的氯化锰（II）和碘化铜（I）的存在下，芳基格氏试剂与碲化乙烯立体定向反应，从而产生相应交叉偶联产物的良好收率。
• The coupling of butylvinyltellurides with organometallic reagents catalysed by nickel complexes
  作者：Cristiano Raminelli、João Gargalaka、Cláudio C. Silveira、João V. Comasseto

  DOI：10.1016/j.tet.2007.06.057

  日期：2007.9

  Vinylic tellurides couple efficiently with sp, sp(2) and sp(3) hybridised organometallic compounds (Li, MgX and Zn species) in the presence of dichloro-bis( triphenylphosphine) nickel(II) as catalyst. (c) 2007 Elsevier Ltd. All rights reserved.
• Diastereoselective synthesis of α,β-unsaturated systems
  作者：Priscila Castelani、João V. Comasseto

  DOI：10.1016/j.tet.2005.01.025

  日期：2005.2

  Functionalized Z-vinylic tellurides were used in substitution reactions with lower order cyanocuprates leading to alpha, beta-unsaturated ketones and esters in good yields. In the case of acyclic tellurides, the product was obtained in high diastereoselectivity. The control of the stereoselectivity was achieved by simple change of the reaction temperature. (C) 2005 Elsevier Ltd. All rights reserved.
• Chemoselective reduction of β-butyltellanyl α,β-unsaturated carbonyl compounds to allylic alcohols
  作者：Alcindo A. Dos Santos、Priscila Castelani、Bruno K. Bassora、José C. Fogo Junior、Carlos E. Costa、João V. Comasseto

  DOI：10.1016/j.tet.2005.06.090

  日期：2005.9

  (Z)-β-Butyltellanyl α,β-unsaturated carbonyl compounds were stereoselectively produced by hydrotelluration of alkynones or by an addition/elimination sequence from enol tosylates. The β-butyltellanyl-enones were chemoselectively reduced with NaBH4/MeOH, NaBH4·CeCl3·7H2O/MeOH and DIBAL-H systems to the corresponding allylic alcohols with retention of the Z stereochemistry.

  （Z）-β-丁基tellanylα，β-不饱和羰基化合物是通过炔烃的加氢酯化反应或烯醇甲苯磺酸盐的加成/消除顺序立体产生的。用NaBH 4 / MeOH，NaBH 4 ·CeCl 3 ·7H 2 O / MeOH和DIBAL-H系统将β-丁基tellanyl-烯酮化学选择性还原为相应的烯丙醇，并保留Z立体化学。