1(R),5(S),4(S)-methyl-2-oxa-bicyclo<3.3.0>oct-6-en-3-one | 137567-95-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 1(R),5(S),4(S)-methyl-2-oxa-bicyclo<3.3.0>oct-6-en-3-one
• 英文别名: (1R,4S,5R)-4-methyl-2-oxabicyclo[3.3.0]-oct-6-en-3-one；(3S,3aR,6aR)-3-methyl-3,3a,6,6a-tetrahydrocyclopenta[b]furan-2-one
• CAS: 137567-95-4
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: COZYOPMCEUEVPF-RRKCRQDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  1(R),5(S),4(S)-methyl-2-oxa-bicyclo<3.3.0>oct-6-en-3-one 在 过氧乙酸 、 sodium acetate 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 51.0h， 生成 (1R,4S,3RS,5R,6R,7S)-6,7-epoxy-4-methyl-2-oxabicyclo[3.3.0]-octan-3-ol
  参考文献：
  名称：

  Synthesis of the C1−C9 Fragment of Callipeltoside-A

  摘要：

  The C1-C9 fragment of callipeltoside (17) was prepared in 12 steps and 7.2% overall yield from bicyclic lactone (+)-4. Key steps include a stereoselective epoxidation and further regiocontrolled nucleophilic opening of the oxirane ring to install two vicinal stereocenters (C5 and C6), and the use of bis(trimethylsilyl) peroxide and a catalytic amount of Sn(IV) chloride for the chemoselective Baeyer-Villiger oxidation of unsaturated cyclopentanone 15.

  DOI：

  10.1021/ol006003y
• 作为产物：
  描述：

  (+)-(1R,4R,5R)-4-methyl-2-oxabicyclo<3.3.0>oct-6-en-3-one 在 lithium hexamethyldisilazane 、 氯化铵 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 2.0h， 以78%的产率得到1(R),5(S),4(S)-methyl-2-oxa-bicyclo<3.3.0>oct-6-en-3-one
  参考文献：
  名称：

  Synthesis of the C1−C9 Fragment of Callipeltoside-A

  摘要：

  The C1-C9 fragment of callipeltoside (17) was prepared in 12 steps and 7.2% overall yield from bicyclic lactone (+)-4. Key steps include a stereoselective epoxidation and further regiocontrolled nucleophilic opening of the oxirane ring to install two vicinal stereocenters (C5 and C6), and the use of bis(trimethylsilyl) peroxide and a catalytic amount of Sn(IV) chloride for the chemoselective Baeyer-Villiger oxidation of unsaturated cyclopentanone 15.

  DOI：

  10.1021/ol006003y

文献信息

• Some Baeyer–Villiger oxidations using a monooxygenase enzyme from Pseudomonas putida NCIMB 10007
  作者：Gideon Grogan、Stanley M. Roberts、Andrew J. Willetts

  DOI：10.1039/c39930000699

  日期：——

  A monooxygenase from Pseudomonas putida NCIMB 10007 is shown to catalyse stereoselective Baeyer–Villiger-type oxidations on the bicyclic ketones 2, 7, 8 and 9.

  来自假单胞菌（Pseudomonas putida）NCIMB 10007的一种单氧化酶被证明可以对二环酮2、7、8和9催化立体选择性Baeyer-Villiger型氧化反应。
• Gombos, Zsuzsanna; Nyitrai, J.; Nagy, J., ACH - Models in Chemistry, 1994, vol. 131, # 3-4, p. 327 - 336
  作者：Gombos, Zsuzsanna、Nyitrai, J.、Nagy, J.、Sohar, P.、Balogh, Gy.、Brlik, J.

  DOI：——

  日期：——
• Synthesis of the C1−C9 Fragment of Callipeltoside-A
  作者：Francisco Velázquez、Horacio F. Olivo

  DOI：10.1021/ol006003y

  日期：2000.6.1

  The C1-C9 fragment of callipeltoside (17) was prepared in 12 steps and 7.2% overall yield from bicyclic lactone (+)-4. Key steps include a stereoselective epoxidation and further regiocontrolled nucleophilic opening of the oxirane ring to install two vicinal stereocenters (C5 and C6), and the use of bis(trimethylsilyl) peroxide and a catalytic amount of Sn(IV) chloride for the chemoselective Baeyer-Villiger oxidation of unsaturated cyclopentanone 15.