7a-chloro-3-methyl-5,6,7,7a-tetrahydro-benzofuran-2(4H)-one | 591231-54-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 7a-chloro-3-methyl-5,6,7,7a-tetrahydro-benzofuran-2(4H)-one
• 英文别名: 2(4H)-Benzofuranone, 7a-chloro-5,6,7,7a-tetrahydro-3-methyl-；7a-chloro-3-methyl-4,5,6,7-tetrahydro-1-benzofuran-2-one
• CAS: 591231-54-8
• 化学式: C₉H₁₁ClO₂
• 分子量: 186.638
• InChiKey: NTXKFFPBINGYQX-UHFFFAOYSA-N

物化性质

• 沸点：
  330.5±30.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  7a-chloro-3-methyl-5,6,7,7a-tetrahydro-benzofuran-2(4H)-one 在 cobalt,triphenylphosphane,chloride 作用下， 以 苯 为溶剂， 反应 2.0h， 以57%的产率得到(RS,RS)-3,3'-dimethyl-4,5,6,7,4',5',6',7'-octahydro[7a,7'a]bibenzofuranyl-2,2'-dione
  参考文献：
  名称：

  Dimerization of Butenolide Structures. A Biomimetic Approach to the Dimeric Sesquiterpene Lactones (±)-Biatractylolide and (±)-Biepiasterolide

  摘要：

  The biomimetic synthesis of the bisesquiterpene lactones (+/-)-biatractylolide 1 and (+/-)-biepiasterolide 2 via dimerization of the captodative stabilized radical 8 is reported. Atractylon 7 has also been shown to be a possible intermediate during the biosynthesis of biatractylolide 1, biepiasterolide 2, atractylolide 3, and hydroxyatractylolide 4.

  DOI：

  10.1021/jo0488053
• 作为产物：
  描述：

  2-(2-oxo-cyclohexyl)-propionic acid 在 rose bengal 氯化亚砜 、 叔丁基锂 、 氧气 、 sodium acetate 、 乙酸酐 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 正戊烷 为溶剂， 反应 27.0h， 生成 7a-chloro-3-methyl-5,6,7,7a-tetrahydro-benzofuran-2(4H)-one
  参考文献：
  名称：

  Dimerization of Butenolide Structures. A Biomimetic Approach to the Dimeric Sesquiterpene Lactones (±)-Biatractylolide and (±)-Biepiasterolide

  摘要：

  The biomimetic synthesis of the bisesquiterpene lactones (+/-)-biatractylolide 1 and (+/-)-biepiasterolide 2 via dimerization of the captodative stabilized radical 8 is reported. Atractylon 7 has also been shown to be a possible intermediate during the biosynthesis of biatractylolide 1, biepiasterolide 2, atractylolide 3, and hydroxyatractylolide 4.

  DOI：

  10.1021/jo0488053

文献信息

• Regioselectivity of dimerisation of butenolides via captodative stabilised radicaloid intermediates
  作者：Sharanjeet K. Bagal、Robert M. Adlington、Rohan A.B. Brown、Jack E. Baldwin

  DOI：10.1016/j.tetlet.2005.04.125

  日期：2005.7

  The regioselective outcome observed during dimerisation of butenolides to dimeric structures via captodative stabilised radicaloids has been studied. The captodative stabilised radicaloids were generated by initial conversion of butenolides to chlorobutenolides via the corresponding hydroxybutenolides, followed by treatment with CoCl(PPh3)3.

  研究了在丁烯内酯通过capdodative稳定的基团二聚化为二聚体结构过程中观察到的区域选择性结果。通过将丁烯内酯通过相应的羟基丁烯内酯初步转化为氯丁烯内酯，然后用CoCl（PPh 3）3处理，生成了具有captodative稳定性的自由基。
• Studies towards the biomimetic synthesis of bisesquiterpene lactones
  作者：Sharanjeet K Bagal、Robert M Adlington、Rodolfo Marquez、Andrew R Cowley、Jack E Baldwin

  DOI：10.1016/s0040-4039(03)01172-9

  日期：2003.6

  A possible biomimetic connection between atractylolide, hydroxyatractylolide and biatractylolide and biepiasterolide has been demonstrated by efficiently generating the biatractylolide and biepiasterolide core structures from atractylolide and hydroxyatractylolide model butenolides via a radicaloid intermediate in a single step in good yield.

  已证明白术内酯，羟白术内酯和双歧内酯与双吡甾醇之间可能存在仿生连接，这是通过在一个步骤中通过自由基型中间体高效地由白术内酯和羟基白术内酯模型丁烯内酯生成双歧内酯和双乳甾醇核心结构来证明的。
• Dimerization of Butenolide Structures. A Biomimetic Approach to the Dimeric Sesquiterpene Lactones (±)-Biatractylolide and (±)-Biepiasterolide
  作者：Sharanjeet K. Bagal、Robert M. Adlington、Jack E. Baldwin、Rodolfo Marquez

  DOI：10.1021/jo0488053

  日期：2004.12.1

  The biomimetic synthesis of the bisesquiterpene lactones (+/-)-biatractylolide 1 and (+/-)-biepiasterolide 2 via dimerization of the captodative stabilized radical 8 is reported. Atractylon 7 has also been shown to be a possible intermediate during the biosynthesis of biatractylolide 1, biepiasterolide 2, atractylolide 3, and hydroxyatractylolide 4.