(R)-6-bromo-2-methyl-2-heptene | 682795-59-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: (R)-6-bromo-2-methyl-2-heptene
• 英文别名: (6R)-6-bromo-2-methylhept-2-ene
• CAS: 682795-59-1
• 化学式: C₈H₁₅Br
• 分子量: 191.111
• InChiKey: JUMQRNMIZZTUOJ-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (R)-6-bromo-2-methyl-2-heptene 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以64%的产率得到(3RS,6R)-6-bromo-2-methyl-2-heptene oxide
  参考文献：
  名称：

  Enantio- and diastereo-convergent synthesis of (2R,5R)- and (2R,5S)-Pityol through enzyme-triggered ring closure

  摘要：

  A short chemoenzymatic synthesis of the (2R,5S)- and (2R,5R)-stereoisomer of the bark beetle pheromone Pityol 1 was achieved from (+/-)-Sulcatol 2 in an enantio- and diastereo-convergent fashion without the formation of any 'unwanted' stereoisomer. The key steps include: (i) lipase-catalyzed deracemization of (+/-)-2 using kinetic resolution coupled to an in-situ inversion or alternatively, dynamic resolution using combined lipase- and Ru-catalysis: and (ii) creation of the second stereogenic center by an epoxide hydrolase-catalyzed diastereo-convergent hydrolysis of a haloalkyl oxirane, followed by spontaneous ring Closure to form 1 in a stereoselective fashion. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(01)00370-6
• 作为产物：
  描述：

  (S)-6-methyl-5-hepten-2-yl acetate 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (R)-6-bromo-2-methyl-2-heptene
  参考文献：
  名称：

  Enantio- and diastereo-convergent synthesis of (2R,5R)- and (2R,5S)-Pityol through enzyme-triggered ring closure

  摘要：

  A short chemoenzymatic synthesis of the (2R,5S)- and (2R,5R)-stereoisomer of the bark beetle pheromone Pityol 1 was achieved from (+/-)-Sulcatol 2 in an enantio- and diastereo-convergent fashion without the formation of any 'unwanted' stereoisomer. The key steps include: (i) lipase-catalyzed deracemization of (+/-)-2 using kinetic resolution coupled to an in-situ inversion or alternatively, dynamic resolution using combined lipase- and Ru-catalysis: and (ii) creation of the second stereogenic center by an epoxide hydrolase-catalyzed diastereo-convergent hydrolysis of a haloalkyl oxirane, followed by spontaneous ring Closure to form 1 in a stereoselective fashion. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(01)00370-6

文献信息

• Enantio- and diastereo-convergent synthesis of (2R,5R)- and (2R,5S)-Pityol through enzyme-triggered ring closure
  作者：Andreas Steinreiber、Klaus Edegger、Sandra F. Mayer、Kurt Faber

  DOI：10.1016/s0957-4166(01)00370-6

  日期：2001.8

  A short chemoenzymatic synthesis of the (2R,5S)- and (2R,5R)-stereoisomer of the bark beetle pheromone Pityol 1 was achieved from (+/-)-Sulcatol 2 in an enantio- and diastereo-convergent fashion without the formation of any 'unwanted' stereoisomer. The key steps include: (i) lipase-catalyzed deracemization of (+/-)-2 using kinetic resolution coupled to an in-situ inversion or alternatively, dynamic resolution using combined lipase- and Ru-catalysis: and (ii) creation of the second stereogenic center by an epoxide hydrolase-catalyzed diastereo-convergent hydrolysis of a haloalkyl oxirane, followed by spontaneous ring Closure to form 1 in a stereoselective fashion. (C) 2001 Published by Elsevier Science Ltd.