methyl (5-methyl-3-oxo)-8-oxabicyclo[3.2.1]octane-2-carboxylate | 124851-63-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: methyl (5-methyl-3-oxo)-8-oxabicyclo[3.2.1]octane-2-carboxylate
• 英文别名: methyl (1S,5R)-5-methyl-3-oxo-8-oxabicyclo[3.2.1]octane-2-carboxylate
• CAS: 124851-63-4；124851-64-5；146430-13-9；146430-28-6
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: KKBFZXDFZJTCHV-HKJUDDBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (5-methyl-3-oxo)-8-oxabicyclo[3.2.1]octane-2-carboxylate 在 水 、 lithium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 2.5h， 以78%的产率得到1-methyl-8-oxabicyclo[3.2.1]octan-3-one
  参考文献：
  名称：

  Total synthesis of (±)-davanone

  摘要：

  The total synthesis of the sesquiterpene (+/-)-davanone is described. A Lewis acid catalyzed [3+4] annulation reaction of 1,4-pentanedione with bis(trimethylsilyl) enol ether 2 is the key synthetic step. The resulting oxabicyclo[3.2.1]heptanone system can be selectively ring-opened and then elaborated further to (+/-)-davanone. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01081-3
• 作为产物：
  描述：

  4-戊酮醛 、 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 以92%的产率得到methyl (5-methyl-3-oxo)-8-oxabicyclo[3.2.1]octane-2-carboxylate
  参考文献：
  名称：

  Total synthesis of (±)-davanone

  摘要：

  The total synthesis of the sesquiterpene (+/-)-davanone is described. A Lewis acid catalyzed [3+4] annulation reaction of 1,4-pentanedione with bis(trimethylsilyl) enol ether 2 is the key synthetic step. The resulting oxabicyclo[3.2.1]heptanone system can be selectively ring-opened and then elaborated further to (+/-)-davanone. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01081-3

文献信息

• Bis(trimethylsilyl) enol ethers as 1,3-dianion equivalents: Regiocontrolled [3+4] and [3+5] annulation reactions
  作者：Gary A. Molander、Steven W. Andrews

  DOI：10.1016/s0040-4039(01)80396-8

  日期：——
• Stereoselective Synthesis of cis-2,5-Disubstituted Tetrahydrofurans Using Oxabicyclo[3.2.1]heptanone Platforms. Building Blocks for Natural Product Synthesis
  作者：Gary A. Molander、Steven Swallow

  DOI：10.1021/jo00102a051

  日期：1994.11
• Total synthesis of (±)-davanone
  作者：Gary A. Molander、Julia Haas

  DOI：10.1016/s0040-4020(98)01081-3

  日期：1999.1

  The total synthesis of the sesquiterpene (+/-)-davanone is described. A Lewis acid catalyzed [3+4] annulation reaction of 1,4-pentanedione with bis(trimethylsilyl) enol ether 2 is the key synthetic step. The resulting oxabicyclo[3.2.1]heptanone system can be selectively ring-opened and then elaborated further to (+/-)-davanone. (C) 1998 Elsevier Science Ltd. All rights reserved.