8,8-Dimethylspiro<4.5>dec-6-ene-1,4-dione | 154029-91-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8,8-Dimethylspiro<4.5>dec-6-ene-1,4-dione
• 英文别名: 8,8-Dimethylspiro[4.5]dec-9-ene-1,4-dione
• CAS: 154029-91-1
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: BMPCDLKCATVQTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8,8-Dimethylspiro<4.5>dec-6-ene-1,4-dione 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (4R^*,5R^*)-4-hydroxy-8,8-dimethylspiro[4.5]dec-6-ene-1-one 、 (4R^*,5S^*)-4-hydroxy-8,8-dimethylspiro[4.5]dec-6-ene-1-one
  参考文献：
  名称：

  面包酵母还原螺[4.5]癸烷-1,4-二酮衍生物的对映体和非对映体选择性

  摘要：

  通过面包酵母介导的减少是在五个螺[4.5]癸烷-1,4-二酮衍生物进行4，9，12，15，和18。对映选择性一直很高，但这与面部非对映选择性无关，其范围从非常高到零。在某些情况下，酵母介导的还原反应的面部选择性低于NaBH 4。4的还原产物在几个步骤中转化为对映体富集的双环中间体5形式，用于合成角三喹烷戊烯1。酵母介导的螺酮21还原 证明了赤道羰基的还原是非常优选的反应方式。

  DOI：

  10.1016/0957-4166(96)00430-2
• 作为产物：
  描述：

  4,4-二甲基-2-环己基-1-酮 、 二(三甲基硅氧基)环丁烯 在 三氟化硼乙醚 、 水 作用下， 生成 8,8-Dimethylspiro<4.5>dec-6-ene-1,4-dione
  参考文献：
  名称：

  Lewis Acid Catalyzed Geminal Acylation Reaction of Ketones with 1,2-Bis[(trimethylsilyl)oxy]cyclobutene: Direct Formation of 2,2-Disubstituted 1,3-Cyclopentanediones

  摘要：

  Ketones reacted with 1,2-bis((trimethylsilyl)oxy)cyclobutene (1) under catalysis by boron trifluoride etherate to yield 2,2-disubstituted 1,3-cyclopentanedione products via silylated cyclobutanone intermediates in a two-step, one-pot process. In many instances addition of a small amount of water to the reaction medium after completion of the first step assisted the subsequent rearrangement to the product, such that reversion of the intermediate to the starting ketone became an insignificant process. Yields were best with cyclohexanones (>90%), but steric hindrance and conjugated double bonds reduced yields considerably.

  DOI：

  10.1021/jo00085a041

文献信息

• Lewis Acid Catalyzed Geminal Acylation Reaction of Ketones with 1,2-Bis[(trimethylsilyl)oxy]cyclobutene: Direct Formation of 2,2-Disubstituted 1,3-Cyclopentanediones
  作者：Tracy J. Jenkins、D. Jean Burnell

  DOI：10.1021/jo00085a041

  日期：1994.3

  Ketones reacted with 1,2-bis((trimethylsilyl)oxy)cyclobutene (1) under catalysis by boron trifluoride etherate to yield 2,2-disubstituted 1,3-cyclopentanedione products via silylated cyclobutanone intermediates in a two-step, one-pot process. In many instances addition of a small amount of water to the reaction medium after completion of the first step assisted the subsequent rearrangement to the product, such that reversion of the intermediate to the starting ketone became an insignificant process. Yields were best with cyclohexanones (>90%), but steric hindrance and conjugated double bonds reduced yields considerably.
• Enantio- and diastereoselectivity in the reduction of spiro[4.5]decane-1,4-dione derivatives with baker's yeast
  作者：Yan-Yi Zhu、D. Jean Burnell

  DOI：10.1016/0957-4166(96)00430-2

  日期：1996.11

  Reductions mediated by baker's yeast were carried out on five spiro[4.5]decane-1,4-dione derivatives 4, 9, 12, 15, and 18. Enantioselectivity was always very high, but this did not correlate with the facial diastereoselectivity, which ranged from very high to zero. In some instances, the facial selectivity of the yeast-mediated reduction was lower than that of NaBH4. The reduction product of 4 was

  通过面包酵母介导的减少是在五个螺[4.5]癸烷-1,4-二酮衍生物进行4，9，12，15，和18。对映选择性一直很高，但这与面部非对映选择性无关，其范围从非常高到零。在某些情况下，酵母介导的还原反应的面部选择性低于NaBH 4。4的还原产物在几个步骤中转化为对映体富集的双环中间体5形式，用于合成角三喹烷戊烯1。酵母介导的螺酮21还原 证明了赤道羰基的还原是非常优选的反应方式。