(1R,2R,6S,7S)-1,7-Dibromo-10,10-dimethoxy-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.0^2,6]decane-8,9-dione | 819070-90-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2R,6S,7S)-1,7-Dibromo-10,10-dimethoxy-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.0^2,6]decane-8,9-dione
• 英文别名: (1S,2S,6R,7R)-1,7-dibromo-10,10-dimethoxy-4,4-dimethyl-3,5-dioxatricyclo[5.2.1.02,6]decane-8,9-dione
• CAS: 819070-90-1
• 化学式: C₁₂H₁₄Br₂O₆
• 分子量: 414.048
• InChiKey: OLFRHAQPQAIPBK-YDRMRZIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2R,6S,7S)-1,7-Dibromo-10,10-dimethoxy-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.0^2,6]decane-8,9-dione 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 amberlyst-15 、 双氧水 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 丙酮 、 苯 为溶剂， 反应 9.0h， 生成 (5R,9R)-9-Hydroxy-7-hydroxymethyl-2,2-dimethyl-1,3-dioxa-spiro[4.4]non-7-en-6-one
  参考文献：
  名称：

  A short and stereoselective synthesis of functionalized pentenomycin derivatives

  摘要：

  A short and stercoselective synthesis of 2-hydroxymethyl-4-deoxypentenomycin and 2-hydoxymethylpentenomycin derivatives is accomplished in five and seven steps starting from tetrabromonorbornyl derivatives in overall yields of 41% and 38%, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.065
• 作为产物：
  描述：

  1,2,3,4-tetrabromo-5,5-dimethoxycyclopenta-1,3-diene 在 ruthenium trichloride sodium periodate 、 水 、 potassium carbonate 、 对苯二酚 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 95.0h， 生成 (1R,2R,6S,7S)-1,7-Dibromo-10,10-dimethoxy-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.0^2,6]decane-8,9-dione
  参考文献：
  名称：

  A short and stereoselective synthesis of functionalized pentenomycin derivatives

  摘要：

  A short and stercoselective synthesis of 2-hydroxymethyl-4-deoxypentenomycin and 2-hydoxymethylpentenomycin derivatives is accomplished in five and seven steps starting from tetrabromonorbornyl derivatives in overall yields of 41% and 38%, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.065

文献信息

• Diastereoselective Synthesis of Spirocyclic Dihydrofurans and 1-Oxaspiro[4.5]decan-6-one Derivatives from Norbornyl α-Diketones
  作者：Surendra H. Mahadevegowda、Faiz Ahmed Khan

  DOI：10.1002/ejoc.201403087

  日期：2015.2

  A diastereoselective zinc-mediated propargylation of non-enolizable norbornyl α-diketones and an efficient AgI-catalyzed cycloisomerization of the resulting α-keto homopropargyl alcohols with terminal alkynes leading to spirocyclic dihydrofurans have been reported. The dihydrofurans obtained were subjected to hydrogenation to afford spiro tetrahydrofuran derivatives in nearly quantitative yields (98-99%)

  据报道，非对映选择性锌介导的非烯醇化降冰片基 α-二酮的炔丙基化和有效的 AgI 催化的 α-酮基高炔丙基醇与末端炔烃的环异构化导致螺环二氢呋喃。获得的二氢呋喃进行氢化以几乎定量的产率(98-99％)提供螺四氢呋喃衍生物。最终，制备的 α-螺四氢呋喃降冰片基单酮用作酸介导的 Grob 型断裂反应的前体，并通过对甲苯磺酸处理转化为 1-oxaspiro[4.5]decan-6-one 衍生物。
• A short and stereoselective synthesis of functionalized pentenomycin derivatives
  作者：Faiz Ahmed Khan、Jyotirmayee Dash、Bhimsen Rout

  DOI：10.1016/j.tetlet.2004.10.065

  日期：2004.12

  A short and stercoselective synthesis of 2-hydroxymethyl-4-deoxypentenomycin and 2-hydoxymethylpentenomycin derivatives is accomplished in five and seven steps starting from tetrabromonorbornyl derivatives in overall yields of 41% and 38%, respectively. (C) 2004 Elsevier Ltd. All rights reserved.