((1R,3R,4R,5R,7R)-7-Ethynyl-4-methyl-2,6-dioxa-bicyclo[3.2.1]oct-3-yl)-methanol | 690634-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: ((1R,3R,4R,5R,7R)-7-Ethynyl-4-methyl-2,6-dioxa-bicyclo[3.2.1]oct-3-yl)-methanol
• 英文别名: [(1R,3R,4R,5R,7R)-7-ethynyl-4-methyl-2,6-dioxabicyclo[3.2.1]octan-3-yl]methanol
• CAS: 690634-38-9
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: MSVIGDFWZCBUTC-IGORNWKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ((1R,3R,4R,5R,7R)-7-Ethynyl-4-methyl-2,6-dioxa-bicyclo[3.2.1]oct-3-yl)-methanol 在 偶氮二异丁腈 、 三正丁基氢锡 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 2.58h， 以77%的产率得到[(1R,3R,4R,5R,7R)-7-((E)-2-Iodo-vinyl)-4-methyl-2,6-dioxa-bicyclo[3.2.1]oct-3-yl]-methanol
  参考文献：
  名称：

  Construction of a C(30−38) Dioxabicyclo[3.2.1]octane Subtarget for (+)-Sorangicin A, Exploiting a Regio- and Stereocontrolled Acid-Catalyzed Epoxide Ring Opening

  摘要：

  In this paper, we report assembly of the novel dioxabicyclo[3.2.1]octane subtarget (-)-2, comprising the signature structural element of the potent antibiotic (+)-sorangicin A (1). The synthesis was achieved in 15 steps (1.5% overall yield) via a series of acid-catalyzed epoxide ring openings, The first, facilitated by the complex of alkyne (+)-3 with Co-2(CO)(8), proceeded in a highly regio- and stereoselective fashion.

  DOI：

  10.1021/ol049644s
• 作为产物：
  描述：

  (2S,3R,4S)-4,5-Bis-(4-methoxy-benzyloxy)-3-methyl-pentane-1,2-diol 在 Oxone 、 lithium aluminium tetrahydride 、 dicobalt octacarbonyl 、 ammonium cerium(IV) nitrate 、 chiral spiro compound 、 三氟化硼乙醚 、 四丁基氟化铵 、 sodium hydride 、 potassium carbonate 、 1-(2,4,6-三异丙基苯基磺酰)咪唑 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 16.51h， 生成 ((1R,3R,4R,5R,7R)-7-Ethynyl-4-methyl-2,6-dioxa-bicyclo[3.2.1]oct-3-yl)-methanol
  参考文献：
  名称：

  Construction of a C(30−38) Dioxabicyclo[3.2.1]octane Subtarget for (+)-Sorangicin A, Exploiting a Regio- and Stereocontrolled Acid-Catalyzed Epoxide Ring Opening

  摘要：

  In this paper, we report assembly of the novel dioxabicyclo[3.2.1]octane subtarget (-)-2, comprising the signature structural element of the potent antibiotic (+)-sorangicin A (1). The synthesis was achieved in 15 steps (1.5% overall yield) via a series of acid-catalyzed epoxide ring openings, The first, facilitated by the complex of alkyne (+)-3 with Co-2(CO)(8), proceeded in a highly regio- and stereoselective fashion.

  DOI：

  10.1021/ol049644s

文献信息

• Construction of a C(30−38) Dioxabicyclo[3.2.1]octane Subtarget for (+)-Sorangicin A, Exploiting a Regio- and Stereocontrolled Acid-Catalyzed Epoxide Ring Opening
  作者：Amos B. Smith、Richard J. Fox

  DOI：10.1021/ol049644s

  日期：2004.4.1

  In this paper, we report assembly of the novel dioxabicyclo[3.2.1]octane subtarget (-)-2, comprising the signature structural element of the potent antibiotic (+)-sorangicin A (1). The synthesis was achieved in 15 steps (1.5% overall yield) via a series of acid-catalyzed epoxide ring openings, The first, facilitated by the complex of alkyne (+)-3 with Co-2(CO)(8), proceeded in a highly regio- and stereoselective fashion.