3-(6-Methyl-1,4,8,11-tetraoxadispiro[4.1.47.25]tridecan-6-yl)propyl methanesulfonate | 1026419-40-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(6-Methyl-1,4,8,11-tetraoxadispiro[4.1.47.25]tridecan-6-yl)propyl methanesulfonate
• CAS: 1026419-40-8
• 化学式: C₁₄H₂₄O₇S
• 分子量: 336.406
• InChiKey: PLKNPEAHWBQNIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(6-Methyl-1,4,8,11-tetraoxadispiro[4.1.47.25]tridecan-6-yl)propyl methanesulfonate 在 amberlyst-15 potassium tert-butylate 、 sodium hydride 、 碳酸氢钠 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 30.0h， 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：

  2-烯丙基-2-甲基-1,3-环戊二酮 在 三氟甲磺酸三甲基硅酯 sodium hydroxide 、 dimethyl sulfide borane 、 双氧水 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 28.17h， 生成 3-(6-Methyl-1,4,8,11-tetraoxadispiro[4.1.47.25]tridecan-6-yl)propyl methanesulfonate
  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).