trans-1-acetoxy-2-<<(methylsulfonyl)oxy>ethyl>-1,3,3-trimethylcyclohexane | 142763-03-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: trans-1-acetoxy-2-<<(methylsulfonyl)oxy>ethyl>-1,3,3-trimethylcyclohexane
• 英文别名: [(1R,2R)-1,3,3-trimethyl-2-(2-methylsulfonyloxyethyl)cyclohexyl] acetate
• CAS: 142763-03-9
• 化学式: C₁₄H₂₆O₅S
• 分子量: 306.423
• InChiKey: MCFOSLHRJBOZCO-TZMCWYRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  trans-1-acetoxy-2-<<(methylsulfonyl)oxy>ethyl>-1,3,3-trimethylcyclohexane 在 sodium hydride 、 三乙胺 、 烯丙醇 、 sodium iodide 作用下， 以 丙酮 、 乙腈 、 正戊烷 为溶剂， 反应 40.58h， 生成 (Z)-2-[2-((1R,2R)-2-Acetoxy-2,6,6-trimethyl-cyclohexyl)-ethyl]-3-trimethylsilanyloxy-hepta-2,6-dienoic acid allyl ester
  参考文献：
  名称：

  Total synthesis of (.+-.)-velloziolone.

  摘要：

  The first total synthesis of the 9,10-seco-kaurene velloziolone (3) has been accomplished using an atom transfer tandem free-radical cyclization to prepare the 6-methylenebicyclo[3.2.1]octan-2-one moiety. The known diol 11 is converted to iodo acetate 10 in three steps. Alkylation of beta-keto ester 22 with 10 affords 33 that is converted to alpha-iodo ketone 7 in one pot by silylation, followed by palladium-catalyzed decarboxylation to give the tetra-substituted silyl enol ether regiospecifically and iodination of the enol ether. Atom transfer cyclization at 150-degrees-C, but not at 25 or 85-degrees-C, provides a mixture of bicyclic iodides. Elimination of HI and hydrolysis of the acetate furnishes velloziolone.

  DOI：

  10.1021/jo00044a024
• 作为产物：
  描述：

  trans-1-acetoxy-2-(2-acetoxyethyl)-1,3,3-trimethylcyclohexane 在 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 trans-1-acetoxy-2-<<(methylsulfonyl)oxy>ethyl>-1,3,3-trimethylcyclohexane
  参考文献：
  名称：

  Total synthesis of (.+-.)-velloziolone.

  摘要：

  The first total synthesis of the 9,10-seco-kaurene velloziolone (3) has been accomplished using an atom transfer tandem free-radical cyclization to prepare the 6-methylenebicyclo[3.2.1]octan-2-one moiety. The known diol 11 is converted to iodo acetate 10 in three steps. Alkylation of beta-keto ester 22 with 10 affords 33 that is converted to alpha-iodo ketone 7 in one pot by silylation, followed by palladium-catalyzed decarboxylation to give the tetra-substituted silyl enol ether regiospecifically and iodination of the enol ether. Atom transfer cyclization at 150-degrees-C, but not at 25 or 85-degrees-C, provides a mixture of bicyclic iodides. Elimination of HI and hydrolysis of the acetate furnishes velloziolone.

  DOI：

  10.1021/jo00044a024