2-(2-iodophenethyl)cyclohexanone | 1537869-55-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-iodophenethyl)cyclohexanone
• CAS: 1537869-55-8
• 化学式: C₁₄H₁₇IO
• 分子量: 328.193
• InChiKey: PHYWWBJJKOZMDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(2-iodophenethyl)cyclohexanone 在 N-甲基咪唑 、 sodium tetrahydroborate 、 Ruphos 、 碘 、 1,2-二溴乙烷 、 三苯基膦 、 lithium chloride 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 57.0h， 生成 1,2,3,4,4a,9,10,10a-octahydrophenanthrene
  参考文献：
  名称：

  Diastereoconvergent Negishi Cross-Coupling Using Functionalized Cyclohexylzinc Reagents

  摘要：

  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.

  DOI：

  10.1021/ol403673e
• 作为产物：
  描述：

  (2-oxocyclohexyl)methyl acetate 在 三甲基氯硅烷 、 copper(l) cyanide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 1,2-二溴乙烷 、 lithium chloride 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 2.5h， 生成 2-(2-iodophenethyl)cyclohexanone
  参考文献：
  名称：

  Diastereoconvergent Negishi Cross-Coupling Using Functionalized Cyclohexylzinc Reagents

  摘要：

  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.

  DOI：

  10.1021/ol403673e

文献信息

• Pd-Catalyzed Stereoselective Construction of Benzo-Fused Decalines with a Quaternary Carbon
  作者：Hideo Setsumasa、Kosuke Imai、Ikumi Kobayashi、Masahisa Nakada

  DOI：10.1021/acs.orglett.3c02233

  日期：2023.11.10

  The Pd-catalyzed stereoselective construction of decalins with one-carbon units bearing heteroatoms at the ring junction is described. The Pd-catalyzed cyclization of silyl enol ether resulted in exclusive formation of the cis isomer (89%, >100/1 cis/trans). On the contrary, Pd-catalyzed carboiodination and carboborylation (with oxidative workup) provided products in 56% yield (1/>100 cis/trans) and

  描述了在环连接处带有杂原子的一碳单元的十氢萘的钯催化立体选择性结构。钯催化的硅烯醇醚环化导致顺式异构体的唯一形成（89%，>100/1顺式/反式）。相反，Pd 催化的碳碘化和碳硼化（带有氧化后处理）分别提供了 56% 产率（1/>100顺式/反式）和 69% 产率（1/11顺式/反式）的产物。