(1'R,3'S)-(-)-cis-(3'-hydroxy-2',2'-dimethyl-6'-methylene-1'-cyclohexyl)methyl 2,2-dimethylpropionate | 475197-95-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1'R,3'S)-(-)-cis-(3'-hydroxy-2',2'-dimethyl-6'-methylene-1'-cyclohexyl)methyl 2,2-dimethylpropionate
• 英文别名: (2S,6R)-(-)-cis-2-hydroxy-γ-cyclogeranyl pivaloate；[(1R,3S)-3-hydroxy-2,2-dimethyl-6-methylidenecyclohexyl]methyl 2,2-dimethylpropanoate
• CAS: 475197-95-6
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: LXFUJHIZDMZWIM-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1'R,3'S)-(-)-cis-(3'-hydroxy-2',2'-dimethyl-6'-methylene-1'-cyclohexyl)methyl 2,2-dimethylpropionate 在 n-butyl tin hydride 、 偶氮二异丁腈 作用下， 以 甲苯 为溶剂， 反应 45.5h， 生成 (1RS,3SR)-3-(hydroxymethyl)-2,2-dimethyl-4-methylenecyclohexanol
  参考文献：
  名称：

  Enantioselective synthesis of both enantiomers of γ-ionone, γ-damascone, karahana lactone and karahana ether

  摘要：

  A straightforward enantioselective synthesis of both enantiomers of the title compounds is described starting from enantiopure methyl (2S,6R)- or (2R,6S)-cis-2-hydroxy-gamma-cyclogeraniate. These versatile building blocks are obtained by biomimetic cyclization of methyl (6S)- or (6R)-(Z)-6,7-epoxy-7-methyl-3-(trimethylsilyl)methyl-2-octenoate, respectively. The chiral information was encoded by a highly regioselective Sharpless asymmetric dihydroxylation of the corresponding diene. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00335-x
• 作为产物：
  描述：

  (1RS,3SR)-3-(hydroxymethyl)-2,2-dimethyl-4-methylenecyclohexanol 、 三甲基乙酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以70%的产率得到(1'R,3'S)-(-)-cis-(3'-hydroxy-2',2'-dimethyl-6'-methylene-1'-cyclohexyl)methyl 2,2-dimethylpropionate
  参考文献：
  名称：

  Enantioselective synthesis of both enantiomers of γ-ionone, γ-damascone, karahana lactone and karahana ether

  摘要：

  A straightforward enantioselective synthesis of both enantiomers of the title compounds is described starting from enantiopure methyl (2S,6R)- or (2R,6S)-cis-2-hydroxy-gamma-cyclogeraniate. These versatile building blocks are obtained by biomimetic cyclization of methyl (6S)- or (6R)-(Z)-6,7-epoxy-7-methyl-3-(trimethylsilyl)methyl-2-octenoate, respectively. The chiral information was encoded by a highly regioselective Sharpless asymmetric dihydroxylation of the corresponding diene. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00335-x

文献信息

• Enantioselective synthesis of both enantiomers of γ-ionone, γ-damascone, karahana lactone and karahana ether
  作者：Stephen Beszant、Elios Giannini、Giuseppe Zanoni、Giovanni Vidari

  DOI：10.1016/s0957-4166(02)00335-x

  日期：2002.7

  A straightforward enantioselective synthesis of both enantiomers of the title compounds is described starting from enantiopure methyl (2S,6R)- or (2R,6S)-cis-2-hydroxy-gamma-cyclogeraniate. These versatile building blocks are obtained by biomimetic cyclization of methyl (6S)- or (6R)-(Z)-6,7-epoxy-7-methyl-3-(trimethylsilyl)methyl-2-octenoate, respectively. The chiral information was encoded by a highly regioselective Sharpless asymmetric dihydroxylation of the corresponding diene. (C) 2002 Elsevier Science Ltd. All rights reserved.