7a-methyl-1-oxo-3,5,6,7-tetrahydro-2H-indene-4-carboxylic acid | 160146-88-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7a-methyl-1-oxo-3,5,6,7-tetrahydro-2H-indene-4-carboxylic acid
• CAS: 160146-88-3
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: QMPJHLRTIPXGSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7a-methyl-1-oxo-3,5,6,7-tetrahydro-2H-indene-4-carboxylic acid 在 N,N-二甲基甲酰胺 4-二甲氨基吡啶 、 草酰氯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (1R,7aS)-1-hydroxy-7a-methyl-1-prop-1-en-2-yl-3,5,6,7-tetrahydro-2H-indene-4-carboxylate
  参考文献：
  名称：

  A New Candidate for a Properly Substituted CD Ring Component of Vitamin D3 via Intramolecular Asymmetric Olefination of a 1,3-Cyclopentanedione Derivative

  摘要：

  A highly diastereoselective synthesis of hydrindenone derivative 5 (98% de) was achieved via diastereotopic differentiation of 1,3-cyclopentanedione derivative 4 by intramolecular Horner-Emmons olefination. In addition, the compound 5 was converted to ketone 2, a new building block far 1 alpha,25-dihydroxyvitamin D-3 (1).

  DOI：

  10.1021/jo00099a002
• 作为产物：
  描述：

  prop-2-enyl 7a-methyl-1-oxo-3,5,6,7-tetrahydro-2H-indene-4-carboxylate 在 palladium diacetate 、 三苯基膦 甲酸 、 三乙胺 作用下， 以 苯 为溶剂， 反应 3.0h， 以81%的产率得到7a-methyl-1-oxo-3,5,6,7-tetrahydro-2H-indene-4-carboxylic acid
  参考文献：
  名称：

  A New Candidate for a Properly Substituted CD Ring Component of Vitamin D3 via Intramolecular Asymmetric Olefination of a 1,3-Cyclopentanedione Derivative

  摘要：

  A highly diastereoselective synthesis of hydrindenone derivative 5 (98% de) was achieved via diastereotopic differentiation of 1,3-cyclopentanedione derivative 4 by intramolecular Horner-Emmons olefination. In addition, the compound 5 was converted to ketone 2, a new building block far 1 alpha,25-dihydroxyvitamin D-3 (1).

  DOI：

  10.1021/jo00099a002

文献信息

• A New Candidate for a Properly Substituted CD Ring Component of Vitamin D3 via Intramolecular Asymmetric Olefination of a 1,3-Cyclopentanedione Derivative
  作者：Tadakatsu Mandai、Yuichi Kaihara、Jiro Tsuji

  DOI：10.1021/jo00099a002

  日期：1994.10

  A highly diastereoselective synthesis of hydrindenone derivative 5 (98% de) was achieved via diastereotopic differentiation of 1,3-cyclopentanedione derivative 4 by intramolecular Horner-Emmons olefination. In addition, the compound 5 was converted to ketone 2, a new building block far 1 alpha,25-dihydroxyvitamin D-3 (1).