(2S,5R,6S)-1-(benzyloxy)-2,6-dimethyldec-9-en-5-ol | 1408299-04-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,5R,6S)-1-(benzyloxy)-2,6-dimethyldec-9-en-5-ol
• 英文别名: (2S,5R,6S)-2,6-dimethyl-1-phenylmethoxydec-9-en-5-ol
• CAS: 1408299-04-6
• 化学式: C₁₉H₃₀O₂
• 分子量: 290.446
• InChiKey: MHNOZRRHJNSOBF-JENIJYKNSA-N

物化性质

• 沸点：
  400.2±45.0 °C(Predicted)
• 密度：
  0.955±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,5R,6S)-1-(benzyloxy)-2,6-dimethyldec-9-en-5-ol 在 氨 、 lithium 、 对甲苯磺酸 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二甲基亚砜 、 苯 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  Asymmetric synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W from 4-pentenoic acid

  摘要：

  A flexible and efficient asymmetric route to the synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W has been accomplished from commercially available 4-pentenoic acid. The successful generation of stereocenters was achieved by utilizing an Evans' chiral auxiliary-based alkylation and aldol reaction. Other key reactions such as a Julia-Kocienski olefination, Kita's macrolactonization, ring closing metathesis (RCM) reaction, and Yamaguchi's esterification were significant for the construction of the macrolactone cores. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.006
• 作为产物：
  描述：

  (S)-5-(phenylmethoxy)-4-methylpentanal 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三氟甲磺酸二丁硼 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 24.67h， 生成 (2S,5R,6S)-1-(benzyloxy)-2,6-dimethyldec-9-en-5-ol
  参考文献：
  名称：

  Asymmetric synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W from 4-pentenoic acid

  摘要：

  A flexible and efficient asymmetric route to the synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W has been accomplished from commercially available 4-pentenoic acid. The successful generation of stereocenters was achieved by utilizing an Evans' chiral auxiliary-based alkylation and aldol reaction. Other key reactions such as a Julia-Kocienski olefination, Kita's macrolactonization, ring closing metathesis (RCM) reaction, and Yamaguchi's esterification were significant for the construction of the macrolactone cores. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.006