5-oxaepilaurene | 119840-40-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-oxaepilaurene
• 英文别名: (2R,3R)-2,3-dimethyl-4-methylidene-2-(4-methylphenyl)oxolane
• CAS: 119840-40-3；119840-41-4
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: LKJGBVPYALNJPH-TZMCWYRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(p-tolyl)but-3-en-2-ol 在 palladium diacetate 、 甲酸 、 sodium hydride 、 三苯基膦 作用下， 以 甲苯 为溶剂， 生成 5-oxaepilaurene
  参考文献：
  名称：

  Reductive elimination of alkylpalladium formate intermediates formed in enyne cyclizations

  摘要：

  Various enynes under the palladium catalysts,were successfully cyclized to the alkylpalladium intermediates, which then were reduced by the hydrogen in a formate ligand (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02704-x

文献信息

• A short synthesis of (±)-laurene: mechanistic reinvestigation in palladium-catalyzed cycloreductions of 1,6-enynes
  作者：Chang Ho Oh、Je Wook Han、Joo Sung Kim、Sung Yong Um、Hyung Hoon Jung、Won Hyung Jang、Ho Shik Won

  DOI：10.1016/s0040-4039(00)01484-2

  日期：2000.10

  Two palladium-catalyzed cycloreduction strategies have been applied for the synthesis of laurene. Palladium-catalyzed cyclizations of 1,6-enynes initially form the corresponding alkylpalladium intermediates. While triethylsilane could directly reduce the intermediates to lead to the corresponding cycloreduced products, the intermediates in the presence of even excess formic acid underwent β-elimination

  两种钯催化的环还原策略已应用于月桂烯的合成。钯催化的1，6-烯炔的环化反应最初形成相应的烷基钯中间体。尽管三乙基硅烷可以直接还原中间体以生成相应的环还原产物，但即使在过量甲酸存在下，该中间体也经过β-消除反应生成二烯，在受阻较小的烯烃上进一步还原二烯以生成环还原产物。
• Regio- and stereoselectivity in palladium-catalyzed cycloreductions of 1,6-enynes in the presence of formic acid or triethylsilane
  作者：Chang Ho Oh、Hyung Hoon Jung、Hye Rhyan Sung、Jung Duk Kim

  DOI：10.1016/s0040-4020(01)00008-4

  日期：2001.2

  Palladium catalyzed 1,6-enyne cycloreductions in the presence of 1.2 equiv. of formic acid (method A) would involve cycloalkylpalladium formates which proceed via two consecutive steps: beta -elimination of alkylpalladium intermediates and then reduction at the less hindered olefins regio- and stereoselectivity. Triethylsilane, however, directly reduced the alkylpalladium intermediates to give the corresponding cycloreduced products (method B). (C) 2001 Elsevier Science Ltd. All rights reserved.
• SRIKRISHNA, A., INDIAN J. CHEM. B, 26,(1987) N 12, C. 1113-1114
  作者：SRIKRISHNA, A.

  DOI：——

  日期：——