(1S,4S)-3-benzenesulfonyl-4-methylcyclohept-2-enol | 474023-06-8

• 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: (1S,4S)-3-benzenesulfonyl-4-methylcyclohept-2-enol
• 英文别名: (1S,4S)-3-(benzenesulfonyl)-4-methylcyclohept-2-en-1-ol
• CAS: 474023-06-8
• 化学式: C₁₄H₁₈O₃S
• 分子量: 266.361
• InChiKey: CVPYGFMUZUUVKI-RYUDHWBXSA-N

物化性质

• 沸点：
  465.1±45.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,4S)-3-benzenesulfonyl-4-methylcyclohept-2-enol 在 氢氧化钾 、 叔丁基锂 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 72.42h， 生成 (-)-4(S)-methylcyclohept-2-enone
  参考文献：
  名称：

  Syntheses of Highly Substituted Enantiopure C6 and C7 Enones¹

  摘要：

  Enantiopure epoxyvinyl sulfones SS-9a, SS-9b, produced from Jacobsen epoxidation of 2-phenylsulfonyl 1,3-cyclohexa- and cycloheptadiene, are used as a template for the construction of substituted cycloalkenones and as chiral synthetic equivalents of enones a and b. The addition of carbon nucleophiles to SS-9a, SS-9b is high yielding and stereospecific. Enantiopure alpha,beta- and gamma-substituted cycloalkenones are easily constructed using a variety of methods.

  DOI：

  10.1021/ja026760m
• 作为产物：
  描述：

  三甲基铝 、 (1S,7S)-(2-phenylsulfonyl)-8-oxabicyclo[5.1.0]oct-2-ene 在 methylcopper 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以91%的产率得到(1S,4S)-3-benzenesulfonyl-4-methylcyclohept-2-enol
  参考文献：
  名称：

  Reagent-Directed Allylic Quadraselection. Chemoselective Anti- and Syn-Lawton S_N2′ Methylation of Seven-Membered Epoxyvinylsulfones

  摘要：

  Methods have been developed for regio- and stereoselective 1,4-syn or 1,4-anti methylation of seven-membered epoxyvinylsulfones. 1,4-Syn addition is achieved via the combination of Me2Zn and catalytic Li2CuCl4, a hitherto unexplored reagent combination. The complementary 1,4-anti addition relies on Cu(I) catalyzed methyl Grignard addition or (CH3)(3)Al assisted CH3Cu addition. The methods described were assayed on four diastereomeric stereodiads and on their parent epoxide.

  DOI：

  10.1021/ja9017557

文献信息

• [EN] LARGE-SCALE DIASTEREOSELECTIVE SYNTHESES OF CYCLOHEPTADIENYLSULFONES AND STEREOTETRADS<br/>[FR] SYNTHESES DIASTEREOSELECTIVES A GRANDE ECHELLE DE CYCLOHEPTADIENYLSULFONES ET DE STEREOTETRADES
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：WO2016057606A1

  公开（公告）日：2016-04-14

  The invention relates to processes for large-scale diastereoselective syntheses of cycloheptadienylsulfone and stereo tetrads, key intermediates for the preparation of Aplyronine A.

  这项发明涉及大规模立体选择性合成环庚二烯基砜和立体四聚体的过程，这些是制备阿普利罗宁A的关键中间体。
• Large-scale diastereoselective syntheses of cycloheptadienylsulfones and stereotetrads
  申请人：Purdue Research Foundation

  公开号：US20170217996A1

  公开（公告）日：2017-08-03

  The invention relates to processes for large-scale diastereoselective syntheses of cycloheptadienylsulfone and stereotetrads, key intermediates for the preparation of Aplyronine A.