(2R,6RS,2'S)-2-(2'-tert-butyldimethylsilyloxypropyl)-6-hydroxy-5,6-dimethyl-2H-pyran-3-one | 409313-31-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R,6RS,2'S)-2-(2'-tert-butyldimethylsilyloxypropyl)-6-hydroxy-5,6-dimethyl-2H-pyran-3-one
• 英文别名: (2R)-2-[(2S)-2-[tert-butyl(dimethyl)silyl]oxypropyl]-6-hydroxy-5,6-dimethylpyran-3-one
• CAS: 409313-31-1
• 化学式: C₁₆H₃₀O₄Si
• 分子量: 314.497
• InChiKey: WMRNJDYHQBLZFD-XNVGXSDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,6RS,2'S)-2-(2'-tert-butyldimethylsilyloxypropyl)-6-hydroxy-5,6-dimethyl-2H-pyran-3-one 在 sodium tetrahydroborate 、 cerium(III) chloride 、 氢氟酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 7.67h， 生成 (1R,3S,5R,6R)-1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-en-6-ol
  参考文献：
  名称：

  Synthesis of (1R,3S,5S)-1,3,8-Trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene, the Male Pheromone of a Hepialid Moth, Endoclita excrescens, and Its Enantiomer

  摘要：

  The (1R,3S,5S)- and (1S,3R,5R)-isomers of 1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene were synthesized from the (S)- and (R)-isomers of ethyl 3-hydroxybutanoate. The (1 R,3S,5S)-isomer was identified as the pheromone produced by the male Japanese hepialid moth, Endoclita excrescens. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  DOI：

  10.1002/1099-0690(200212)2002:23<3974::aid-ejoc3974>3.0.co;2-z
• 作为产物：
  描述：

  (S)-3-(tert-butyldimethylsilyloxy)butanal 在 叔丁基锂 、 间氯过氧苯甲酸 作用下， 以 六甲基磷酰三胺 、 乙醚 、 二氯甲烷 为溶剂， 生成 (2R,6RS,2'S)-2-(2'-tert-butyldimethylsilyloxypropyl)-6-hydroxy-5,6-dimethyl-2H-pyran-3-one
  参考文献：
  名称：

  Synthesis of (1R,3S,5S)-1,3,8-Trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene, the Male Pheromone of a Hepialid MothEndoclita excrescens, and Its Enantiomer

  摘要：

  (1R,3S,5S)-和(1S,3R,5R)-异构体的1,3,8-三甲基-2,9-二氧双环[3.3.1]诺烯是分别从(S)-和(R)-异构体的乙基3-羟基丁酸酯合成的。(1R,3S,5S)-异构体被鉴定为日本蛾类的雄性性信息素，艾诺克丽塔蛾（Endoclita excrescens）。

  DOI：

  10.1246/cl.2002.40

文献信息

• Synthesis of (1<i>R</i>,3<i>S</i>,5<i>S</i>)-1,3,8-Trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene, the Male Pheromone of a Hepialid Moth<i>Endoclita excrescens</i>, and Its Enantiomer
  作者：Kaoru Marukawa、Kenji Mori

  DOI：10.1246/cl.2002.40

  日期：2002.1

  Both (1R,3S,5S)- and (1S,3R,5R)-isomers of 1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene were synthesized by starting from (S)- and (R)-isomers of ethyl 3-hydroxybutanoate, respectively. The (1R,3S,5S)-isomer was identified as the male sex pheromone of a Japanese hepialid moth, Endoclita excrescens.

  (1R,3S,5S)-和(1S,3R,5R)-异构体的1,3,8-三甲基-2,9-二氧双环[3.3.1]诺烯是分别从(S)-和(R)-异构体的乙基3-羟基丁酸酯合成的。(1R,3S,5S)-异构体被鉴定为日本蛾类的雄性性信息素，艾诺克丽塔蛾（Endoclita excrescens）。
• Synthesis of (1R,3S,5S)-1,3,8-Trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene, the Male Pheromone of a Hepialid Moth, Endoclita excrescens, and Its Enantiomer
  作者：Kaoru Marukawa、Kenji Mori

  DOI：10.1002/1099-0690(200212)2002:23<3974::aid-ejoc3974>3.0.co;2-z

  日期：2002.12

  The (1R,3S,5S)- and (1S,3R,5R)-isomers of 1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene were synthesized from the (S)- and (R)-isomers of ethyl 3-hydroxybutanoate. The (1 R,3S,5S)-isomer was identified as the pheromone produced by the male Japanese hepialid moth, Endoclita excrescens. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)