(4S,5Z,10R)-4-hydroxy-10-methyl-3,4,7,8,9,10-hexahydro-2H-oxecin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奥昔康唑
• 英文名称: (4S,5Z,10R)-4-hydroxy-10-methyl-3,4,7,8,9,10-hexahydro-2H-oxecin-2-one
• 英文别名: (2R,6Z,8S)-8-hydroxy-2-methyl-2,3,4,5,8,9-hexahydrooxecin-10-one
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: QBMOXZAUNMFTMZ-FXFQRMSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (5R)-5-[1-(tert-butyl)-1,1-diphenylsilyl]oxyhexanal 在 Grubbs catalyst first generation 吡啶 、 正丁基锂 、 2,4,6-三氯苯甲酰氯 、 氢氟酸 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 93.5h， 生成 (4S,5Z,10R)-4-hydroxy-10-methyl-3,4,7,8,9,10-hexahydro-2H-oxecin-2-one
  参考文献：
  名称：

  Stereoselective synthesis of (+)-diplodialides-B, C and a formal synthesis of (+)-diplodialide-A by ring-closing metathesis approach

  摘要：

  Stereoselective synthesis of diplodialides-B and C and the formal synthesis of diplodialide-A are reported. A combination of Jacobsen's hydrolytic kinetic resolution and Sharpless epoxidation is used for the creation of two stereogenic centers, while a ring-closing metathesis strategy was used for the construction of the lactone ring. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.045

文献信息

• Stereoselective synthesis of (+)-diplodialides-B, C and a formal synthesis of (+)-diplodialide-A by ring-closing metathesis approach
  作者：G.V.M. Sharma、K. Laxmi Reddy

  DOI：10.1016/j.tetasy.2006.11.045

  日期：2006.12

  Stereoselective synthesis of diplodialides-B and C and the formal synthesis of diplodialide-A are reported. A combination of Jacobsen's hydrolytic kinetic resolution and Sharpless epoxidation is used for the creation of two stereogenic centers, while a ring-closing metathesis strategy was used for the construction of the lactone ring. (c) 2006 Elsevier Ltd. All rights reserved.