(3R,3aS,7S,7aR)-7-methyl-3-(phenylmethoxymethyl)-3a,4,5,6,7,7a-hexahydro-3H-2-benzofuran-1-one | 325981-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: (3R,3aS,7S,7aR)-7-methyl-3-(phenylmethoxymethyl)-3a,4,5,6,7,7a-hexahydro-3H-2-benzofuran-1-one
• CAS: 325981-92-8
• 化学式: C₁₇H₂₂O₃
• 分子量: 274.36
• InChiKey: UOPAPDMOZTYMKH-DRPJVOAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,3aS,7S,7aR)-7-methyl-3-(phenylmethoxymethyl)-3a,4,5,6,7,7a-hexahydro-3H-2-benzofuran-1-one 在 palladium on activated charcoal sodium tetrahydroborate 、 sodium periodate 、 lithium aluminium tetrahydride 、 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 10.0h， 生成 (1RS,2SR,3SR)-2-(hydroxymethyl-2,3-dimethylcyclohexyl)methanol
  参考文献：
  名称：

  Regiocontrol of Radical Cyclization by Lewis Acids. Efficient Synthesis of Optically Active Functionalized Cyclopentanes and Cyclohexanes

  摘要：

  [GRAPHICS]Treatment of alpha -alkylidenelactones 3a-d with Bu3SnH and a catalytic amount of Et3B effected a 5-exo radical cyclization preferentially to provide the corresponding 1 and 2 in a ratio of 70:30 to 100:0, Meanwhile, the reaction of 3a and 3b in the presence of Et2AlCl proceeded via a B-endo cyclization pathway predominantly to afford 2a and 2b with 90% and 92% regioselectivity, respectively.

  DOI：

  10.1021/ol0067890
• 作为产物：
  描述：

  (E)-6-[(tert-butyldimethylsilyl)oxy]-2-hexen-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二异丙酯 、 三乙基硼 、 三正丁基氢锡 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.5h， 生成 (3R,3aS,7S,7aR)-7-methyl-3-(phenylmethoxymethyl)-3a,4,5,6,7,7a-hexahydro-3H-2-benzofuran-1-one
  参考文献：
  名称：

  Regiocontrol of Radical Cyclization by Lewis Acids. Efficient Synthesis of Optically Active Functionalized Cyclopentanes and Cyclohexanes

  摘要：

  [GRAPHICS]Treatment of alpha -alkylidenelactones 3a-d with Bu3SnH and a catalytic amount of Et3B effected a 5-exo radical cyclization preferentially to provide the corresponding 1 and 2 in a ratio of 70:30 to 100:0, Meanwhile, the reaction of 3a and 3b in the presence of Et2AlCl proceeded via a B-endo cyclization pathway predominantly to afford 2a and 2b with 90% and 92% regioselectivity, respectively.

  DOI：

  10.1021/ol0067890

文献信息

• Regiocontrol of Radical Cyclization by Lewis Acids. Efficient Synthesis of Optically Active Functionalized Cyclopentanes and Cyclohexanes
  作者：Kwangho Kim、Sentaro Okamoto、Fumie Sato

  DOI：10.1021/ol0067890

  日期：2001.1.1

  [GRAPHICS]Treatment of alpha -alkylidenelactones 3a-d with Bu3SnH and a catalytic amount of Et3B effected a 5-exo radical cyclization preferentially to provide the corresponding 1 and 2 in a ratio of 70:30 to 100:0, Meanwhile, the reaction of 3a and 3b in the presence of Et2AlCl proceeded via a B-endo cyclization pathway predominantly to afford 2a and 2b with 90% and 92% regioselectivity, respectively.