3,5,5-trimethylcyclohex-2-en-1-yl 1-bromo-2-methoxyprop-2-yl ether | 166984-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5,5-trimethylcyclohex-2-en-1-yl 1-bromo-2-methoxyprop-2-yl ether
• 英文别名: 3-[(1-Bromo-2-methoxypropan-2-yl)oxy]-1,5,5-trimethylcyclohex-1-ene；3-(1-bromo-2-methoxypropan-2-yl)oxy-1,5,5-trimethylcyclohexene
• CAS: 166984-93-6
• 化学式: C₁₃H₂₃BrO₂
• 分子量: 291.228
• InChiKey: QWTNVIHMKITINX-UHFFFAOYSA-N

物化性质

• 沸点：
  319.0±37.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5,5-trimethylcyclohex-2-en-1-yl 1-bromo-2-methoxyprop-2-yl ether 在 jones reagent 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 丙酮 、 苯 为溶剂， 反应 2.58h， 生成
  参考文献：
  名称：

  A radical cyclisation based cyclopentenone annulation of allyl alcohols

  摘要：

  A four-step cyclopentenone annulation reaction of allylic alcohols employing a 5-exo-trig radical cyclisation reaction of mixed allyl methyl ketals of bromoacetone as the key step is described. The annulated product 1215 obtained from 2.3-dimethylcyclohexenol has been further elaborated into (+/-)-epibakkenolides employing a 5-exo-dig radical cylisation reaction based alpha-spiro-beta-methvlene-gamma-butyrolactone annulation methodology. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00535-4
• 作为产物：
  描述：

  2-甲氧基丙烯 、 3,5,5-三甲基-2-环己烯-1-醇 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到3,5,5-trimethylcyclohex-2-en-1-yl 1-bromo-2-methoxyprop-2-yl ether
  参考文献：
  名称：

  新的四氢呋喃串联基团环化反应-还原脱氧序列

  摘要：

  用三丁基氯化锡，氰基硼氢化钠和AIBN处理衍生自烯丙醇的溴缩酮可为四氢呋喃化产物提供5- trig自由基环化反应，然后还原性裂解缩酮。

  DOI：

  10.1016/0040-4039(94)02412-5

文献信息

• Tributyltin chloride-sodium cyanoborohydride mediated tandem radical cyclisation-reductive demethoxylation sequence
  作者：A Srikrishna、R Viswajanani、C.V Yelamaggad

  DOI：10.1016/s0040-4020(97)00658-3

  日期：1997.7

  the bromoketals 3, 7a-g and 11 with tri-n-butyltin chloride and sodium cyanoborohydride in the presence of a catalytic amount of AIBN furnished the ethers 5, 8a-g and 13 via a tandem sequence comprising of a radical cyclisation reaction and tri-n-butylhalostannane and sodium cyanoborohydride mediated reductive demethoxylation of the resulting cyclic ketals.

  所述bromoketals的反应3，图7a-克和11用三正丁基锡氯化物和氰基硼氢化钠在AIBN催化量的存在提供的醚5，图8A-G和13经由串联序列，其包含自由基环化反应的以及三正丁基卤烷烃和氰基硼氢化钠介导的环状缩酮的还原性脱甲氧基化。
• A new tetrahydrofurannulation tandem radical cyclisation reaction-reductive deoxygenation sequence
  作者：A Srikrishna、R Viswajanani、C.V Yelamaggad

  DOI：10.1016/0040-4039(94)02412-5

  日期：1995.2

  Treatment of bromoketals , derived from allyl alcohols , with tributyltin chloride, sodium cyanoborohydride and AIBN furnishes the tetrahydrofurannulated products a 5--trig radical cyclisation reaction followed by reductive cleavage of ketal .

  用三丁基氯化锡，氰基硼氢化钠和AIBN处理衍生自烯丙醇的溴缩酮可为四氢呋喃化产物提供5- trig自由基环化反应，然后还原性裂解缩酮。
• A mild and simple procedure for the reductive cleavage of acetals and ketals
  作者：Adusumilli Srikrishna、Ranganathan Viswajanani

  DOI：10.1016/0040-4020(95)00055-d

  日期：1995.3

  A convenient, mild and simple procedure, employing sodium cyanoborohydride in the presence of either catalytic or stoichiometric amount of boron trifluoride etherate in dry THF, for the reductive cleavage of the acetals and ketals is described.

  描述了一种方便，温和且简单的方法，该方法在催化或化学计量的三氟化硼醚化物在干燥THF中的存在下使用氰基硼氢化钠进行缩醛和缩酮的裂解。
• Cyclopentaannulation of allyl alcohols via a radical cyclisation reaction. Total synthesis of 4-epibakkenolide-A
  作者：A. Srikrishna、R. Viswajanani、J. A. Sattigeri

  DOI：10.1039/c39950000469

  日期：——

  A four step cyclopentaannulation methodology starting from allyl alcohols using 5-exo-trig radical cyclisation as the key reaction, and its application to the total synthesis of 4-epibakkenolide is described.

  描述了以烯丙醇为原料，以 5-exo-trig 自由基环化为关键反应的四步环戊环化方法，及其在 4-epibakkenolide 全合成中的应用。
• A radical cyclisation based cyclopentenone annulation of allyl alcohols
  作者：A. Srikrishna、R. Viswajanani、J.A. Sattigeri

  DOI：10.1016/s0957-4166(03)00535-4

  日期：2003.10

  A four-step cyclopentenone annulation reaction of allylic alcohols employing a 5-exo-trig radical cyclisation reaction of mixed allyl methyl ketals of bromoacetone as the key step is described. The annulated product 1215 obtained from 2.3-dimethylcyclohexenol has been further elaborated into (+/-)-epibakkenolides employing a 5-exo-dig radical cylisation reaction based alpha-spiro-beta-methvlene-gamma-butyrolactone annulation methodology. (C) 2003 Elsevier Ltd. All rights reserved.