(4S)-1,1-dibromo-4,8-dimethylnonane | 1356399-80-8

• 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: (4S)-1,1-dibromo-4,8-dimethylnonane
• CAS: 1356399-80-8
• 化学式: C₁₁H₂₂Br₂
• 分子量: 314.104
• InChiKey: CCNJHSYYCWWPLD-JTQLQIEISA-N

物化性质

• 沸点：
  287.2±8.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (4S)-1,1-dibromo-4,8-dimethylnonane 在 potassium hydride 、 1,3-丙二胺 作用下， 以 mineral oil 为溶剂， 反应 3.0h， 以99%的产率得到(4S)-4,8-dimethylnon-1-yne
  参考文献：
  名称：

  Stereoselective synthesis of the insect growth regulator (S)-(+)-hydroprene through Suzuki–Miyaura cross-coupling

  摘要：

  A stereoselective synthesis of the insect growth regulator (S)-(+)-hydroprene has been developed in seven steps with 50% overall yield starting from an easily available bromoester. Through using the Suzuki-Miyaura cross-coupling as the key C-sp2-C-sp2 bond forming step, high level of stereocontrol of the C2-C3 olefin is achieved. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.019
• 作为产物：
  描述：

  (R)-甲基-5-溴-4-甲基戊酸酯 在 亚磷酸三苯酯 、 lithium aluminium tetrahydride 、 草酰氯 、 溴 、 magnesium 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (4S)-1,1-dibromo-4,8-dimethylnonane
  参考文献：
  名称：

  Stereoselective synthesis of the insect growth regulator (S)-(+)-hydroprene through Suzuki–Miyaura cross-coupling

  摘要：

  A stereoselective synthesis of the insect growth regulator (S)-(+)-hydroprene has been developed in seven steps with 50% overall yield starting from an easily available bromoester. Through using the Suzuki-Miyaura cross-coupling as the key C-sp2-C-sp2 bond forming step, high level of stereocontrol of the C2-C3 olefin is achieved. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.019

文献信息

• Stereoselective synthesis of the insect growth regulator (S)-(+)-hydroprene through Suzuki–Miyaura cross-coupling
  作者：Shunji Zhang、Huaide Dong、Jinghan Gui、Weisheng Tian

  DOI：10.1016/j.tetlet.2012.02.019

  日期：2012.4

  A stereoselective synthesis of the insect growth regulator (S)-(+)-hydroprene has been developed in seven steps with 50% overall yield starting from an easily available bromoester. Through using the Suzuki-Miyaura cross-coupling as the key C-sp2-C-sp2 bond forming step, high level of stereocontrol of the C2-C3 olefin is achieved. (C) 2012 Elsevier Ltd. All rights reserved.