(Z)-4-(n-butyltelanyl)-3-penten-2-one | 251991-67-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-4-(n-butyltelanyl)-3-penten-2-one
• 英文别名: (Z)-4-(butyltellanyl)pent-3-en-2-one；(Z)-4-butyltellanylpent-3-en-2-one
• CAS: 251991-67-0
• 化学式: C₉H₁₆OTe
• 分子量: 267.825
• InChiKey: RIEUSTGGOBLNNV-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (Z)-4-(n-butyltelanyl)-3-penten-2-one 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 (Z)-4-(butyltellanyl)pent-3-en-2-ol
  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：

  乙酰丙酮 在 碲化氢 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.5h， 生成 (Z)-4-(n-butyltelanyl)-3-penten-2-one
  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

• A general method of synthesis of functionalized Z-vinylic tellurides starting from β-dicarbonyl compounds
  作者：Rafael E Barrientos-Astigarraga、Priscila Castelani、Celso Y Sumida、Julio Zukerman-Schpector、João V Comasseto

  DOI：10.1016/s0040-4020(01)01204-2

  日期：2002.2

  Z-Vinylic tellurides are prepared by stereoselective vinylic substitution on Z/E mixtures of enolphosphates, acetates, tosylates and triflates by organotellurolates. The reaction is sensitive to the nature of the organotellurolate; the aromatic derivatives react slower than the aliphatic ones. The reaction time is not influenced by the nature of the leaving group.

  Z- Vinylic碲化物是通过在烯醇磷酸酯，乙酸酯，甲苯磺酸酯和三氟甲磺酸酯的Z / E混合物上通过立体立体乙烯基化合物进行立体选择性乙烯基取代而制得的。该反应对有机碲酸根的性质敏感。芳香族衍生物的反应比脂肪族衍生物慢。反应时间不受离去基团性质的影响。
• Synthesis of functionalized tri- and tetrasubstituted vinylic tellurides from enolphosphates through vinylic substitution by lithium butyltellurolate
  作者：R.E Barrientos-Astigarraga、P Castelani、C.Y Sumida、J.V Comasseto

  DOI：10.1016/s0040-4039(99)01633-0

  日期：1999.10

  Vinylic tellurides are precursors of important highly reactive vinylic organometallics (e.g. vinyl Li and Cu species). Herein we report that tri- and tetrasubstituted functionalized vinylic tellurides can be prepared from enolphosphates through a vinylic substitution by lithium butyltellurolate. Starting from mixtures of Z- and E-enolphosphates, only the Z-vinylic telluride is formed.

  乙烯基碲化物是重要的高反应性乙烯基有机金属（例如乙烯基Li和Cu物质）的前体。在本文中，我们报道可以通过烯丙基磷酸酯通过碲酸丁二酸锂的乙烯基取代来制备三和四取代的官能化的乙烯基碲化物。从Z-和E-烯醇磷酸酯的混合物开始，仅形成Z-乙烯基碲化物。
• Carbon–carbon bond formation by means of organotellurium compounds
  作者：R Barrientos-Astigarraga

  DOI：10.1016/s0022-328x(00)00828-7

  日期：2001.3.30

  vinylic halides, phosphates, sulphonates and acetates leading to the Z vinylic telluride exclusively. Tellurides are transmetallated with easily available organometallic reagents to give valuable synthetic building blocks (e.g. organolithiums and organocuprates). Reaction of vinylic tellurides with alkynes under Pd catalysis or with organocuprates gives the coupling products with retention of the double bond

  Z乙烯基碲化物是通过在非还原条件下使用n -BuLi–Te–H 2 O作为加氢灭菌系统对炔烃进行加氢灭菌而制得的。相同的系统促进了含有吸电子基团的烯烃的加氢酯化反应。锂和有机碲酸镁可对乙烯基卤化物，磷酸盐，磺酸盐和乙酸盐进行乙烯基取代，从而独家生成Z乙烯基碲化物。碲化物用容易获得的有机金属试剂进行金属转移，从而得到有价值的合成基础材料（例如，有机锂和有机铜酸盐）。乙烯基碲化物与Pd催化下的炔烃或与有机铜酸盐的反应，使偶联产物保持了双键的几何形状。
• 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。