(3AR,7AS)-2-oxo-3-phenylselenyl-4,4,7a-trimethyloctahydrobenzofuran | 104446-40-4

• 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: (3AR,7AS)-2-oxo-3-phenylselenyl-4,4,7a-trimethyloctahydrobenzofuran
• 英文别名: 4,4,7a-trimethyl-3-phenylselanyl-3a,5,6,7-tetrahydro-3H-1-benzofuran-2-one
• CAS: 104446-40-4
• 化学式: C₁₇H₂₂O₂Se
• 分子量: 337.32
• InChiKey: WNCJMSIPEUQBIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  (3AR,7AS)-2-oxo-3-phenylselenyl-4,4,7a-trimethyloctahydrobenzofuran 在 双氧水 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 4.5h， 以90%的产率得到二氢猕猴桃内酯
  参考文献：
  名称：

  Total synthesis of (±)-dihydroactinidiolide using selenium-stabilized carbenium ion

  摘要：

  A new, short total synthesis of dihydroactinidiolide 1 is described using selenium carbenium ion-promoted carbon-carbon bond formation as the key step. Our synthetic strategy starts with a lactonization reaction between 1,3,3-trimethylcyclohexene 13 and alpha-chloro-alpha-phenylseleno ethyl acetate 14, affording the key intermediate, alpha-phenylseleno-gamma-butyro lactone 15, which reacted via a selenoxide elimination to the target compound 1. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.067
• 作为产物：
  描述：

  1,3,3-三甲基环己烯 、 ethyl α-chloro-α-phenylseleno acetate 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以45%的产率得到(3AR,7AS)-2-oxo-3-phenylselenyl-4,4,7a-trimethyloctahydrobenzofuran
  参考文献：
  名称：

  Total synthesis of (±)-dihydroactinidiolide using selenium-stabilized carbenium ion

  摘要：

  A new, short total synthesis of dihydroactinidiolide 1 is described using selenium carbenium ion-promoted carbon-carbon bond formation as the key step. Our synthetic strategy starts with a lactonization reaction between 1,3,3-trimethylcyclohexene 13 and alpha-chloro-alpha-phenylseleno ethyl acetate 14, affording the key intermediate, alpha-phenylseleno-gamma-butyro lactone 15, which reacted via a selenoxide elimination to the target compound 1. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.067

文献信息

• Total synthesis of (±)-dihydroactinidiolide using selenium-stabilized carbenium ion
  作者：Miguel J. Dabdoub、Claudio C. Silveira、Eder J. Lenardão、Palimécio G. Guerrero、Luiz H. Viana、Cristiane Y. Kawasoko、Adriano C.M. Baroni

  DOI：10.1016/j.tetlet.2009.07.067

  日期：2009.10

  A new, short total synthesis of dihydroactinidiolide 1 is described using selenium carbenium ion-promoted carbon-carbon bond formation as the key step. Our synthetic strategy starts with a lactonization reaction between 1,3,3-trimethylcyclohexene 13 and alpha-chloro-alpha-phenylseleno ethyl acetate 14, affording the key intermediate, alpha-phenylseleno-gamma-butyro lactone 15, which reacted via a selenoxide elimination to the target compound 1. (C) 2009 Elsevier Ltd. All rights reserved.