(4-(tert-butyl)cyclohexyl)zinc iodide | 1285537-33-8

• 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: (4-(tert-butyl)cyclohexyl)zinc iodide
• CAS: 1285537-33-8；1537869-24-1；154669-67-7
• 化学式: C₁₀H₁₉IZn
• 分子量: 331.555
• InChiKey: UUEZBMXSWDQRJT-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (4-(tert-butyl)cyclohexyl)zinc iodide 生成 1-tert-butyl-4-deuterio-cyclohexane
  参考文献：
  名称：

  Duddu Rajagopal, Eckhardt Matthias, Furlong Michael, Knoess H. Peter, Ber+, Tetrahedron, 50 (1994) N 8, S 2415-2432

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(tert-butyl)-4-iodocyclohexane 生成 (4-(tert-butyl)cyclohexyl)zinc iodide
  参考文献：
  名称：

  Duddu Rajagopal, Eckhardt Matthias, Furlong Michael, Knoess H. Peter, Ber+, Tetrahedron, 50 (1994) N 8, S 2415-2432

  摘要：

  DOI：

文献信息

• Stereoselective Retentive Domino Transmetalations of Secondary Alkyllithium Compounds to Functionalized Secondary Alkylcopper Reagents
  作者：Kohei Moriya、Meike Simon、Rasmus Mose、Konstantin Karaghiosoff、Paul Knochel

  DOI：10.1002/anie.201505740

  日期：2015.9.7

  obtained by I/Li exchange from the corresponding secondary alkyl iodides undergo two successive transmetalations with Me3SiCH2ZnBr⋅LiBr and CuBr⋅2 LiCl⋅Me2S to provide functionalized secondary alkylcopper compounds with high retention of configuration. These alkylcopper derivatives react further with electrophiles such as alkynyl esters, acid chlorides, allylic chlorides, ketals, ethylene oxide, and 3‐iodocyclopentanone

  通过I / Li交换从相应的仲烷基碘化物中获得的功能化的仲烷基锂试剂与Me 3 SiCH 2 ZnBr·LiBr和CuBr· 2 LiCl·Me 2 S进行了两次连续的重金属化，从而提供了高度保留结构的功能化的仲烷基铜化合物。这些烷基铜衍生物进一步与亲电子试剂反应，如炔基酯，酰基氯，烯丙基氯，缩酮，环氧乙烷和3-碘代环戊酮，并具有很高的构型保留率。与MeMgI和LaCl 3进行金属转移的相关序列⋅2LiCl允许将烷基仲锂试剂保持性添加到丙酮中。描述了溶剂对仲烷基锌试剂构型稳定性的影响。
• Diastereoconvergent Negishi Cross-Coupling Using Functionalized Cyclohexylzinc Reagents
  作者：Kohei Moriya、Paul Knochel

  DOI：10.1021/ol403673e

  日期：2014.2.7

  Highly diastereoselective Pd-catalyzed cross-coupling reactions of functionalized 2-, 3-, and 4-substituted cyclohexylzinc reagents with aryl, heteroaryl, and alkenyl iodides have been performed under mild conditions. The use of Ruphos (2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl) as a ligand as well as LiCl and N-ethylpyrrolidone (NEP) as additives leads to especially high diastereoselectivities and displays good functional group tolerance. The stereoselectivity can be explained by assuming that the intermediate palladium moiety occupies an equatorial position of the cyclohexyl ring.