(1R,5R,8S)-4,4,8-trimethyl-3-oxatricyclo[6.3.0.0(1,5)]undecan-2,11-dione | 1269249-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,5R,8S)-4,4,8-trimethyl-3-oxatricyclo[6.3.0.0(1,5)]undecan-2,11-dione
• 英文别名: (1R,5R,8S)-4,4,8-trimethyl-3-oxatricyclo[6.3.0.01,5]undecane-2,11-dione
• CAS: 1269249-81-1
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: AHJWMDMWIKCBDR-AQUOVQTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,5R,8S)-4,4,8-trimethyl-3-oxatricyclo[6.3.0.0(1,5)]undecan-2,11-dione 在 sodium tetrahydroborate 、 potassium hydride 作用下， 以 paraffin oil 为溶剂， 生成 (1R,5R,8S,11S)-4,4,8,10,10-pentamethyl-11-phenylmethoxy-3-oxatricyclo[6.3.0.01,5]undecan-2-one
  参考文献：
  名称：

  Aliphatic C−H to C−C Conversion: Synthesis of (−)-Cameroonan-7α-ol

  摘要：

  In the course of a synthesis of the tricyclic sesquiterpene (-)-cameroonan-7 alpha-ol from the acyclic (+)-citronellal, seven aliphatic C-H bonds were converted to C-C bonds, and three rings and four new stereogenic centers were established.

  DOI：

  10.1021/jo200075v
• 作为产物：
  描述：

  (R)-(+)-β-香茅醇 在 吡啶 、 辛酸铑 、 copper(II) acetate monohydrate 、 manganese(III) triacetate dihydrate 、 溶剂黄146 、 三乙胺 、 甲烷磺酰基叠氮化物 、 三氟乙酸 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 32.25h， 生成 (1R,5R,8S)-4,4,8-trimethyl-3-oxatricyclo[6.3.0.0(1,5)]undecan-2,11-dione
  参考文献：
  名称：

  Aliphatic C−H to C−C Conversion: Synthesis of (−)-Cameroonan-7α-ol

  摘要：

  In the course of a synthesis of the tricyclic sesquiterpene (-)-cameroonan-7 alpha-ol from the acyclic (+)-citronellal, seven aliphatic C-H bonds were converted to C-C bonds, and three rings and four new stereogenic centers were established.

  DOI：

  10.1021/jo200075v

文献信息

• Aliphatic C−H to C−C Conversion: Synthesis of (−)-Cameroonan-7α-ol
  作者：Douglass F. Taber、Christopher G. Nelson

  DOI：10.1021/jo200075v

  日期：2011.3.18

  In the course of a synthesis of the tricyclic sesquiterpene (-)-cameroonan-7 alpha-ol from the acyclic (+)-citronellal, seven aliphatic C-H bonds were converted to C-C bonds, and three rings and four new stereogenic centers were established.