(2S,5R,6S)-5-((2-methoxyethoxy)methoxy)-2,6-dimethyldec-9-enoic acid | 1408299-09-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,5R,6S)-5-((2-methoxyethoxy)methoxy)-2,6-dimethyldec-9-enoic acid
• 英文别名: (2S,5R,6S)-5-(2-methoxyethoxymethoxy)-2,6-dimethyldec-9-enoic acid
• CAS: 1408299-09-1
• 化学式: C₁₆H₃₀O₅
• 分子量: 302.411
• InChiKey: LXOCIQHWYQJBHE-SOUVJXGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,5R,6S)-5-((2-methoxyethoxy)methoxy)-2,6-dimethyldec-9-enoic acid 、 (S)-1-(benzyloxy)but-3-en-2-ol 在 2,4,6-三氯苯甲酰氯 、 N,N-二异丙基乙胺 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以75%的产率得到(2S,5R,6S)-((S)-1-(benzyloxy)but-3-en-2-yl) 5-((2-methoxyethoxy)methoxy)-2,6-dimethyldec-9-enoate
  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：

  在 lithium aluminium tetrahydride 、 重铬酸吡啶 、 氨 、 lithium 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (2S,5R,6S)-5-((2-methoxyethoxy)methoxy)-2,6-dimethyldec-9-enoic acid
  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