tert-butyl-[(2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoxy]-dimethylsilane | 204326-64-7

• 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: tert-butyl-[(2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoxy]-dimethylsilane
• CAS: 204326-64-7
• 化学式: C₂₆H₄₄OSi
• 分子量: 400.72
• InChiKey: MXLHWHHSTDVNQC-KMYDTGTFSA-N

物化性质

• 沸点：
  467.8±14.0 °C(Predicted)
• 密度：
  0.903±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.54
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tert-butyl-[(2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoxy]-dimethylsilane 在 barium permanganate 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 11-顺式视黄醛
  参考文献：
  名称：

  Stereocontrolled Synthesis of (11Z)-Retinal and Its Analogues

  摘要：

  Suzuki coupling of stereochemically pure (Z)-bromotetraene 1-which is extremely unstable but can be kept in frozen benzene in the presence of a small amount of PPh3 at &sminus 01;20°C-and (Z)-alkenylboronic acid 2 provides the stereocontrolled synthesis of (11Z)-retinal 3. The 11Z configuration, which is introduced by selective catalytic debromination of the corresponding dibromo precursor of 1, is retained in this step. TBDMS = tBuMe2 Si.

  DOI：

  10.1002/(sici)1521-3773(19980216)37:3<320::aid-anie320>3.0.co;2-4
• 作为产物：
  描述：

  (7E,9E)-beta-离子亚基乙醛 在 四(三苯基膦)钯 三正丁基氢锡 、 三苯基膦 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 0.41h， 生成 tert-butyl-[(2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoxy]-dimethylsilane
  参考文献：
  名称：

  Stereocontrolled Synthesis of (11Z)-Retinal and Its Analogues

  摘要：

  Suzuki coupling of stereochemically pure (Z)-bromotetraene 1-which is extremely unstable but can be kept in frozen benzene in the presence of a small amount of PPh3 at &sminus 01;20°C-and (Z)-alkenylboronic acid 2 provides the stereocontrolled synthesis of (11Z)-retinal 3. The 11Z configuration, which is introduced by selective catalytic debromination of the corresponding dibromo precursor of 1, is retained in this step. TBDMS = tBuMe2 Si.

  DOI：

  10.1002/(sici)1521-3773(19980216)37:3<320::aid-anie320>3.0.co;2-4

文献信息

• On the thermal sigmatropic rearrangement of allenic retinoids: 12,14-retro-retinol
  作者：Javier Sueiras、William H. Okamura

  DOI：10.1021/ja00540a013

  日期：1980.9
• Stereocontrolled Synthesis of (11Z)-Retinal and Its Analogues
  作者：Jun'ichi Uenishi、Reiko Kawahama、Osamu Yonemitsu、Akimori Wada、Masayoshi Ito

  DOI：10.1002/(sici)1521-3773(19980216)37:3<320::aid-anie320>3.0.co;2-4

  日期：1998.2.16

  Suzuki coupling of stereochemically pure (Z)-bromotetraene 1-which is extremely unstable but can be kept in frozen benzene in the presence of a small amount of PPh3 at &sminus 01;20°C-and (Z)-alkenylboronic acid 2 provides the stereocontrolled synthesis of (11Z)-retinal 3. The 11Z configuration, which is introduced by selective catalytic debromination of the corresponding dibromo precursor of 1, is retained in this step. TBDMS = tBuMe2 Si.