1-(p-methylphenylsulfonyl)-2-(octylidene)cyclopropyl methyl ketone | 1054565-63-7

• 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-(p-methylphenylsulfonyl)-2-(octylidene)cyclopropyl methyl ketone
• CAS: 1054565-63-7
• 化学式: C₂₀H₂₈O₃S
• 分子量: 348.507
• InChiKey: VTJZGLSQFYQKLU-VCHYOVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  51.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(p-methylphenylsulfonyl)-2-(octylidene)cyclopropyl methyl ketone 在 N-碘代丁二酰亚胺 作用下， 以 水 、 乙腈 为溶剂， 反应 40.0h， 以62%的产率得到(1RS,2RS,4SR,5SR)-1-(p-methylphenylsulfonyl)-2-methyl-4-heptyl-5-iodo-3-oxabicyclo[3.1.0]hexan-2-ol
  参考文献：
  名称：

  Studies on the factors controlling the stereoselectivity in electrophilic iodocyclization of alkylidenecyclopropyl ketones

  摘要：

  An efficient electrophilic iodocyclization of alkylidenecyclopropyl ketones with N-iodosuccinimide (NIS) or l(2) in aqueous CH3CN affording 3-oxabicyclo[3.1.0]hexan-2-ols is described. NIS is a better electrophilic iodocyclization reagent than l(2). Four chiral centers were formed within one step. The stereochemistry was established by the X-ray diffraction studies of compounds 2e-2h, 2n, and 2c. It is quite interesting to observe that the substituent of the cyclopropane ring plays an important role in determining the relative stereochemistry at the 4-position: with R-2 being an acyl or ester group a mixture of (1S*,2R*,4S*5R*)-2 (major) and (1R*,2R*,4R*,5R*)-2 (minor) was formed with moderate selectivity while the reaction of the substrates with R being sulfonyl and p-methylphenylsulfonyl or R-1 being phenyl afforded (1R*,2R*,4S*,5S*)-2 or (1S*,2R*,4S*,5R*)-2f as the only product. The reaction is general for a range of different substrates to afford the products in moderate to high yields. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.060
• 作为产物：
  描述：

  癸-1,2-二烯 、 1-diazo-1-tosylpropan-2-one 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 以15%的产率得到1-(p-methylphenylsulfonyl)-2-(octylidene)cyclopropyl methyl ketone
  参考文献：
  名称：

  Studies on the factors controlling the stereoselectivity in electrophilic iodocyclization of alkylidenecyclopropyl ketones

  摘要：

  An efficient electrophilic iodocyclization of alkylidenecyclopropyl ketones with N-iodosuccinimide (NIS) or l(2) in aqueous CH3CN affording 3-oxabicyclo[3.1.0]hexan-2-ols is described. NIS is a better electrophilic iodocyclization reagent than l(2). Four chiral centers were formed within one step. The stereochemistry was established by the X-ray diffraction studies of compounds 2e-2h, 2n, and 2c. It is quite interesting to observe that the substituent of the cyclopropane ring plays an important role in determining the relative stereochemistry at the 4-position: with R-2 being an acyl or ester group a mixture of (1S*,2R*,4S*5R*)-2 (major) and (1R*,2R*,4R*,5R*)-2 (minor) was formed with moderate selectivity while the reaction of the substrates with R being sulfonyl and p-methylphenylsulfonyl or R-1 being phenyl afforded (1R*,2R*,4S*,5S*)-2 or (1S*,2R*,4S*,5R*)-2f as the only product. The reaction is general for a range of different substrates to afford the products in moderate to high yields. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.060