cis-1,6-Dimethylbicyclo<4.3.0>non-3-en-8-on | 41065-57-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-1,6-Dimethylbicyclo<4.3.0>non-3-en-8-on
• 英文别名: (3AR,7AS)-3A,7A-Dimethyl-1,3,3A,4,7,7A-hexahydro-2H-inden-2-one；(3aS,7aR)-3a,7a-dimethyl-1,3,4,7-tetrahydroinden-2-one
• CAS: 41065-57-0
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: NAJWWFVAXVYPJR-PHIMTYICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cis-1,6-Dimethylbicyclo<4.3.0>non-3-en-8-on 在 cyclopentadecanone monooxygenase-expressing Escherichia coli 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Extensive substrate profiling of cyclopentadecanone monooxygenase as Baeyer–Villiger biocatalyst reveals novel regiodivergent oxidations

  摘要：

  Cyclopentadecanone monooxygenase (CPDMO) is one of the latest additions to the established library of Baeyer-Villiger monooxygenases. Desymmetrizations of substituted cyclobutanones and -hexanones as well as kinetic resolutions of racemic cycloketones are efficiently catalyzed by CPDMO. Moreover the enzyme shows unprecedented preference in regiodivergent oxidations of terpenones and the bicyclic Geissman-Waiss lactone precursor giving access to the optical antipode of retronecine and other pyrrolizidine alkaloids. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.07.003
• 作为产物：
  描述：

  [(1S,6R)-1,6-Dimethyl-6-([[(4-methylphenyl)sulfonyl]oxy]methyl)-3-cyclohexen-1-YL]methyl 4-methylbenzenesulfonate 在 sodium hydroxide 、 sodium hydride 、 barium(II) oxide 作用下， 以 乙二醇 、 二甲基亚砜 为溶剂， 235.0~260.0 ℃ 、7.33 kPa 条件下， 生成 cis-1,6-Dimethylbicyclo<4.3.0>non-3-en-8-on
  参考文献：
  名称：

  .alpha.-Halo sulfones. XXI. Bishomoconjugative rearrangement pathway. Structural bond relocation attending the dehydrohalogenation of unsaturated cyclic .alpha.-halo ketones and sulfones

  摘要：

  DOI：

  10.1021/ja00788a023

文献信息

• Geometrical limitations in the intramolecular addition of unsymmetrical allylsilanes to enones
  作者：George Majetich、Ken Hull、Jean Defauw、Thomas Shawe

  DOI：10.1016/s0040-4039(00)94903-7

  日期：1985.1

  The geometrical constraints of the fluoride-initiated and Lewis acid-catalyzed intramolecular addition of allylsilanes to enone systems were shown to be governed by kinetic-ring-size preferences. Molecules containing adjacent quaternary carbon atoms can be prepared using this method.

  氟化物引发的和路易斯酸催化的烯丙基硅烷分子内烯丙基硅烷分子内加成的几何约束条件受动力学环大小偏好的支配。可以使用该方法制备包含相邻的季碳原子的分子。
• .alpha.-Halo sulfones. XXI. Bishomoconjugative rearrangement pathway. Structural bond relocation attending the dehydrohalogenation of unsaturated cyclic .alpha.-halo ketones and sulfones
  作者：Leo A. Paquette、Robert H. Meisinger、Robert E. Wingard

  DOI：10.1021/ja00788a023

  日期：1973.4
• Extensive substrate profiling of cyclopentadecanone monooxygenase as Baeyer–Villiger biocatalyst reveals novel regiodivergent oxidations
  作者：Michael J. Fink、Thomas C. Fischer、Florian Rudroff、Hanna Dudek、Marco W. Fraaije、Marko D. Mihovilovic

  DOI：10.1016/j.molcatb.2011.07.003

  日期：2011.12

  Cyclopentadecanone monooxygenase (CPDMO) is one of the latest additions to the established library of Baeyer-Villiger monooxygenases. Desymmetrizations of substituted cyclobutanones and -hexanones as well as kinetic resolutions of racemic cycloketones are efficiently catalyzed by CPDMO. Moreover the enzyme shows unprecedented preference in regiodivergent oxidations of terpenones and the bicyclic Geissman-Waiss lactone precursor giving access to the optical antipode of retronecine and other pyrrolizidine alkaloids. (C) 2011 Elsevier B.V. All rights reserved.