(8R,11S)-8-((S)-hex-5-en-2-yl)-11-methyl-14-phenyl-2,5,7,13-tetraoxotetradecane | 1408299-07-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (8R,11S)-8-((S)-hex-5-en-2-yl)-11-methyl-14-phenyl-2,5,7,13-tetraoxotetradecane
• CAS: 1408299-07-9
• 化学式: C₂₃H₃₈O₄
• 分子量: 378.552
• InChiKey: BYUSOKUWQRMMLJ-QNWVGRARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  27.0
• 可旋转键数：
  17.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (8R,11S)-8-((S)-hex-5-en-2-yl)-11-methyl-14-phenyl-2,5,7,13-tetraoxotetradecane 在 重铬酸吡啶 、 氨 、 lithium 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 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
• 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 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 24.67h， 生成 (8R,11S)-8-((S)-hex-5-en-2-yl)-11-methyl-14-phenyl-2,5,7,13-tetraoxotetradecane
  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