trans-2,6-dimethyl-2-methoxy-3-octen-8-ol | 675868-68-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: trans-2,6-dimethyl-2-methoxy-3-octen-8-ol
• 英文别名: (R,E)-7-methoxy-3,7-dimethyloct-5-en-1-ol；(E,3R)-7-methoxy-3,7-dimethyloct-5-en-1-ol
• CAS: 675868-68-5
• 化学式: C₁₁H₂₂O₂
• 分子量: 186.294
• InChiKey: IZIYRSGDEQZPDQ-VHODGJRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-2,6-dimethyl-2-methoxy-3-octen-8-ol 在 盐酸 作用下， 以 正己烷 为溶剂， 反应 3.0h， 以94%的产率得到d-rose oxide
  参考文献：
  名称：

  Rose Oxides: A Facile Chemo and Chemo‐Enzymatic Approach

  摘要：

  Nonracemic rose oxides were synthesized from racemic or nonracemic monoterpene alcohol citronellol by a novel chemo and chemo-enzymatic route. After the key step of bromomethoxylation of citronellol, the intermediate was dehydrobrominated by a base, followed by an acid catalyzed demethoxylation along with cyclization to furnish rose oxides in high yield. The racemic dehydrobrominated precursor was also kinetically resolved using various lipases to produce nonracemic rose oxides.

  DOI：

  10.1080/00397910500186425
• 作为产物：
  描述：

  (R)-(+)-β-香茅醇 在 氢氧化钾 、 1,3-二溴-5,5-二甲基海因 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 7.0h， 生成 trans-2,6-dimethyl-2-methoxy-3-octen-8-ol
  参考文献：
  名称：

  Rose Oxides: A Facile Chemo and Chemo‐Enzymatic Approach

  摘要：

  Nonracemic rose oxides were synthesized from racemic or nonracemic monoterpene alcohol citronellol by a novel chemo and chemo-enzymatic route. After the key step of bromomethoxylation of citronellol, the intermediate was dehydrobrominated by a base, followed by an acid catalyzed demethoxylation along with cyclization to furnish rose oxides in high yield. The racemic dehydrobrominated precursor was also kinetically resolved using various lipases to produce nonracemic rose oxides.

  DOI：

  10.1080/00397910500186425

文献信息

• Unconventional Fragment Usage Enables a Concise Total Synthesis of (−)-Callyspongiolide
  作者：Francesco Manoni、Corentin Rumo、Liubo Li、Patrick G. Harran

  DOI：10.1021/jacs.7b13591

  日期：2018.1.31

  An asymmetric synthesis of (-)-callyspongiolide is described. The route builds the macrolide domain atypically from a disaccharide and a monoterpene without passing through a seco-acid. Chiral iridium catalysis selectively joins fragments. Subsequent degradation of an imbedded butyrolactone via perhemiketal fragmentation affords a stereo- and regio-defined homoallylic alcohol that is engaged directly

  描述了 (-)-callyspongiolide 的不对称合成。该路线非典型地从二糖和单萜构建大环内酯结构域，而无需通过节酸。手性铱催化选择性地连接片段。随后通过全缩酮裂解嵌入的丁内酯降解提供立体和区域定义的高烯丙醇，其直接参与羰基化大环内酯化。多不饱和附属物的进一步加工以特别直接和灵活的方式提供了天然产品。
• Rose Oxides: A Facile Chemo and Chemo‐Enzymatic Approach
  作者：Subhash C. Taneja、Vijay K. Sethi、Samar S. Andotra、Surrinder Koul、Ghulam N. Qazi

  DOI：10.1080/00397910500186425

  日期：2005.9.1

  Nonracemic rose oxides were synthesized from racemic or nonracemic monoterpene alcohol citronellol by a novel chemo and chemo-enzymatic route. After the key step of bromomethoxylation of citronellol, the intermediate was dehydrobrominated by a base, followed by an acid catalyzed demethoxylation along with cyclization to furnish rose oxides in high yield. The racemic dehydrobrominated precursor was also kinetically resolved using various lipases to produce nonracemic rose oxides.