1-acetylcyclohexane-2,4,6-triisopropylbenzenesulfonyl hydrazone | 83477-69-4

• 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: 1-acetylcyclohexane-2,4,6-triisopropylbenzenesulfonyl hydrazone
• 英文别名: N-(1-cyclohexylethylideneamino)-2,4,6-tri(propan-2-yl)benzenesulfonamide
• CAS: 83477-69-4
• 化学式: C₂₃H₃₈N₂O₂S
• 分子量: 406.633
• InChiKey: HKZQREUIXFGQEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.29
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  58.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-acetylcyclohexane-2,4,6-triisopropylbenzenesulfonyl hydrazone 在 potassium tert-butylate 、 lithium hexamethyldisilazane 、 环丁砜 、 2,6-二叔丁基-4-甲基苯酚 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以81.7%的产率得到乙烯基环己烷
  参考文献：
  名称：

  一种乙烯基环己烷的制备方法

  摘要：

  本发明公开了一种乙烯基环己烷的制备方法，属于有机合成技术领域。以环己基甲酮为原料，首先与2,4,6‑三异丙基苯磺酰肼缩合得到1‑乙酰环己烷‑2,4,6‑三异丙基苯磺酰腙；随后在无机碱和非亲核强碱存在下反应得到乙烯基环己烷。该方法两步反应，路线简单，区域选择高，产品分离相对容易，产品蒸馏时需要加入一定量阻聚剂防止蒸馏过程中聚合。

  公开号：

  CN112707779A
• 作为产物：
  描述：

  2,4,6-三异丙基苯磺酰基肼 、 乙酰基环己烷 在 频哪醇 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以98%的产率得到1-acetylcyclohexane-2,4,6-triisopropylbenzenesulfonyl hydrazone
  参考文献：
  名称：

  一种乙烯基环己烷的制备方法

  摘要：

  本发明公开了一种乙烯基环己烷的制备方法，属于有机合成技术领域。以环己基甲酮为原料，首先与2,4,6‑三异丙基苯磺酰肼缩合得到1‑乙酰环己烷‑2,4,6‑三异丙基苯磺酰腙；随后在无机碱和非亲核强碱存在下反应得到乙烯基环己烷。该方法两步反应，路线简单，区域选择高，产品分离相对容易，产品蒸馏时需要加入一定量阻聚剂防止蒸馏过程中聚合。

  公开号：

  CN112707779A

文献信息

• A convergent method for the stereoselective synthesis of trisubstituted alkenes
  作者：Stephen F. Martin、Dilon Daniel、Robert J. Cherney、Spiros Liras

  DOI：10.1021/jo00035a004

  日期：1992.4

  A method for the stereoselective, convergent synthesis of trisubstituted alkenes has been developed. The procedure features the synthesis of allylic alcohols 9 by coupling an aldehyde with a vinyl organometallic reagent. Treatment of 9 with carbon disulfide and methyl iodide gave the intermediate allylic xanthates 10 that underwent facile [3,3]-sigmatropic rearrangement to give the dithiocarbonates 11 and 12, radical reduction of which gave the (E)-alkenes 13 as the major products.
• Improved preparations of some arenesulfonylhydrazones
  作者：Steven H. Bertz、Gary Dabbagh

  DOI：10.1021/jo00149a022

  日期：1983.1
• Addition of diphenylphosphine oxide to arenesulfonylhydrazones: novel adducts from tosylhydrazones and a new synthesis of alkyldiphenylphosphine oxides from trisylhydrazones
  作者：Steven H. Bertz、Gary Dabbagh

  DOI：10.1021/ja00409a063

  日期：1981.9
• A Novel Palladium-Catalyzed Asymmetric Cyclocarbonylation of Allylic Alcohols to γ-Butyrolactones
  作者：Wing-Yiu Yu、Corinne Bensimon、Howard Alper

  DOI：10.1002/chem.19970030313

  日期：——

  AbstractA catalyst system based on [Pd2(dba)3]·CHCl3/(‐)‐BPPM has been found to effect asymmetric cyclocarbonylation of certain prochiral allylic alcohols to produce good yields of optically enriched γ‐butyrolactones. The reaction was performed under an atmosphere of H2 (400 psi) and CO (400 psi) at 100°C in methylene chloride for 48 hours. Asymmetric cyclocarbonylation of allylic alcohols with aliphatic substituents proceeded with moderate enantioselectivities (ee = 25–43%). However, enantiomeric excesses of up to 83% were obtained for substrates containing aromatic substituents, in which case the ee was found to be more sensitive to steric, rather than to electronic factors. Recrystallization of the lactones containing an aromatic group from a mixture of CH2Cl2/Et2O/hexanes (0.5/1.0/8.5), by slow evaporation of the solvent or at low temperature, improved the enantiopurities to >98% ee on a reproducible basis. The asymmetric center of the aromatic lactones was assigned the (S)‐configuration based on the X‐ray crystal structure analysis of enantiopure (S)‐(+)‐3,3‐dimethyl‐2‐(2′‐methylphenyl)‐γ‐butyrolactone (2k). A hydridopalladium intermediate is believed to play a key role in this reaction. Enantioselectivity is thought to be brought about by the preferential formation of 6b. The carbon skeleton of 6b fits into the chiral scaffold of (‐)‐BPPM.