(2R,3S)-trans-3-phenyl-2-(2-propenyl)cyclohexanone

• 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: (2R,3S)-trans-3-phenyl-2-(2-propenyl)cyclohexanone
• 英文别名: (2R,3S)-trans-3-phenyl-2-allylcyclohexanone；(2R,3S)-3-phenyl-2-prop-2-enylcyclohexan-1-one
• 化学式: C₁₅H₁₈O
• 分子量: 214.307
• InChiKey: MYCVAFZUTCSBCZ-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 phenyltriisopropoxytitanium(IV) 、 3-溴丙烯 在 [Rh(OH)((S)-binap)]2 、 lithium isopropoxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以82%的产率得到(2R,3S)-trans-3-phenyl-2-(2-propenyl)cyclohexanone
  参考文献：
  名称：

  芳基钛试剂的铑催化不对称 1,4-加成生成手性钛烯醇化物：分离为甲硅烷基烯醇醚

  摘要：

  在 3 mol % [Rh(OH)((S )- binap)]2 在 THF 中在 20 摄氏度下得到高产率的钛烯醇化物作为 1,4-加成产物。通过用三甲基氯硅烷和异丙醇锂处理，钛烯醇化物被转化为甲硅烷基烯醇醚。

  DOI：

  10.1021/ja027663w

文献信息

• Merging Pd ⁰ /Pd ^II Redox and Pd ^II /Pd ^II Non‐redox Catalytic Cycles for the Allylarylation of Electron‐Deficient Alkenes
  作者：Kazuhiko Semba、Naoki Ohta、Fritz Paulus、Masaki Ohata、Yoshiaki Nakao

  DOI：10.1002/chem.202100075

  日期：2021.3.12

  An allylarylation of electron‐deficient alkenes with aryl boronates and allylic carbonates has been developed. This method allows access to a wide variety of carbon skeletons from readily available starting materials. Mechanistic studies indicate that this reaction is enabled by a cooperative catalysis based on merging Pd0/PdII redox and PdII/PdII non‐redox catalytic cycles.

  已经开发出了缺电子烯烃与硼酸芳基酯和烯丙基碳酸酯的烯丙基芳基化反应。该方法允许从容易获得的起始原料中获得各种各样的碳骨架。机理研究表明，该反应是通过基于Pd 0 / Pd II氧化还原和Pd II / Pd II非氧化还原催化循环的协同催化而实现的。
• Generation of Chiral Boron Enolates by Rhodium-Catalyzed Asymmetric 1,4-Addition of 9-Aryl-9-borabicyclo[3.3.1]nonanes (<i>B</i>-Ar-9BBN) to α,β-Unsaturated Ketones
  作者：Kazuhiro Yoshida、Masamichi Ogasawara、Tamio Hayashi

  DOI：10.1021/jo020659i

  日期：2003.3.1

  Asymmetric 1,4-addition of 9-phenyl-9-borabicyclo[3.3.1]nonane (2m) to 2-cyclohexenone (1a) proceeded with high enantioselectivity in toluene at 80 degreesC in the presence of 3 mol % of a rhodium catalyst generated from [Rh(OMe)(cod)](2) and (S)-binap to give a high yield of boron enolate (S)-3am, which is 98% enantiomerically pure. Reaction of the boron enolate 3am with electrophiles, methanol-d, propanal, and allyl bromide, gave the corresponding 2-substituted (3S)-3-phenylcyclohexanones with perfect regio- and diastereoselectivity.
• Rhodium-Catalyzed Asymmetric 1,4-Addition of Aryltitanium Reagents Generating Chiral Titanium Enolates:  Isolation as Silyl Enol Ethers
  作者：Tamio Hayashi、Norihito Tokunaga、Kazuhiro Yoshida、Jin Wook Han

  DOI：10.1021/ja027663w

  日期：2002.10.1

  triisopropoxide (ArTi(OPr-i )3) to alpha,beta-unsaturated ketones proceeded with high enantioselectivity (94-99.8% ee) in the presence of 3 mol % of [Rh(OH)((S )-binap)]2 in THF at 20 degrees C to give high yields of the titanium enolates as 1,4-addition products. The titanium enolates were converted into silyl enol ethers by treatment with chlorotrimethylsilane and lithium isopropoxide.

  在 3 mol % [Rh(OH)((S )- binap)]2 在 THF 中在 20 摄氏度下得到高产率的钛烯醇化物作为 1,4-加成产物。通过用三甲基氯硅烷和异丙醇锂处理，钛烯醇化物被转化为甲硅烷基烯醇醚。