4-[(tert-butydimethylsilyl)oxy]-2-(chloromethyl)cyclohex-2-ene-1-one | 1569273-15-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[(tert-butydimethylsilyl)oxy]-2-(chloromethyl)cyclohex-2-ene-1-one
• 英文别名: 4-[Tert-butyl(dimethyl)silyl]oxy-2-(chloromethyl)cyclohex-2-en-1-one；4-[tert-butyl(dimethyl)silyl]oxy-2-(chloromethyl)cyclohex-2-en-1-one
• CAS: 1569273-15-9
• 化学式: C₁₃H₂₃ClO₂Si
• 分子量: 274.863
• InChiKey: SGNMWNSATHOKCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[(tert-butydimethylsilyl)oxy]-2-(chloromethyl)cyclohex-2-ene-1-one 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 双[Α,Α-双(三氟甲基)苯甲醇合]二苯硫 、 四丁基氟化铵 、 氯化二乙基铝 、 tetraethyl-ammonium, trichloride 、 lithium carbonate 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.92h， 生成
  参考文献：
  名称：

  A Synthesis of the ABC Tricyclic Core of the Clionastatins Serves To Corroborate Their Proposed Structures

  摘要：

  A synthesis of the ABC tricyclic ring system of the clionastatins, an unusual pair of highly chlorinated androstane steroids, has been accomplished. This work provides strong support for the original structural proposal. An unexpected substrate-dependent reversal in alkene chlorination diastereoselectivity was critical to success. This approach should be amenable to an eventual enantioselective synthesis of the natural products themselves.

  DOI：

  10.1021/ol500265v
• 作为产物：
  描述：

  2-hydroxymethyl-4-O-(tert-butyldimethylsilyl)cyclohex-2-en-1-on-4-ol 在 tetraethyl-ammonium, trichloride 、 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以79%的产率得到4-[(tert-butydimethylsilyl)oxy]-2-(chloromethyl)cyclohex-2-ene-1-one
  参考文献：
  名称：

  A Synthesis of the ABC Tricyclic Core of the Clionastatins Serves To Corroborate Their Proposed Structures

  摘要：

  A synthesis of the ABC tricyclic ring system of the clionastatins, an unusual pair of highly chlorinated androstane steroids, has been accomplished. This work provides strong support for the original structural proposal. An unexpected substrate-dependent reversal in alkene chlorination diastereoselectivity was critical to success. This approach should be amenable to an eventual enantioselective synthesis of the natural products themselves.

  DOI：

  10.1021/ol500265v

文献信息

• A Synthesis of the ABC Tricyclic Core of the Clionastatins Serves To Corroborate Their Proposed Structures
  作者：Samuel S. Tartakoff、Christopher D. Vanderwal

  DOI：10.1021/ol500265v

  日期：2014.3.7

  A synthesis of the ABC tricyclic ring system of the clionastatins, an unusual pair of highly chlorinated androstane steroids, has been accomplished. This work provides strong support for the original structural proposal. An unexpected substrate-dependent reversal in alkene chlorination diastereoselectivity was critical to success. This approach should be amenable to an eventual enantioselective synthesis of the natural products themselves.