ethyl 2-[(1'R,2'S,4'aR,8'aS)-1',2',4'a-trimethylspiro[1,3-dioxolane-2,5'-3,4,6,7,8,8a-hexahydro-2H-naphthalene]-1'-yl]acetate | 199180-28-4

• 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: ethyl 2-[(1'R,2'S,4'aR,8'aS)-1',2',4'a-trimethylspiro[1,3-dioxolane-2,5'-3,4,6,7,8,8a-hexahydro-2H-naphthalene]-1'-yl]acetate
• CAS: 199180-28-4
• 化学式: C₁₉H₃₂O₄
• 分子量: 324.461
• InChiKey: GQIOVIUFZMRILV-CWLKWCNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(1'R,2'S,4'aR,8'aS)-1',2',4'a-trimethylspiro[1,3-dioxolane-2,5'-3,4,6,7,8,8a-hexahydro-2H-naphthalene]-1'-yl]acetate 在 lithium aluminium tetrahydride 、 正丁基锂 、 2-硝基苯基丝氰酸酯 、 三丁基膦 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 (2-methoxy-6-(methoxymethoxy)phenyl)((4aS,5R,6S,8aR)-5,6,8a-trimethyloctahydro-2H-spiro[naphthalene-1,2'-[1,3]dioxolan]-5-yl)methanol
  参考文献：
  名称：

  Studies toward the Total Synthesis of Popolohuanone E:  Enantioselective Synthesis of 8-O-MethylpopolohuanoneE

  摘要：

  [GRAPHIC]8-O-Methylpopolohuanone E (2) was synthesized in a highly convergent manner starting from the cis-fused decalin derivative accessible from the (-)-Wieland-Miescher ketone analogue. The synthetic method features a biogenetic-type annulation of the phenolic and quinone segments to regioselectively construct the central tricyclic ring system as the key step.

  DOI：

  10.1021/ol016285h
• 作为产物：
  描述：

  (4'aR,8'aS)-1',4'a-dimethylspiro[1,3-dioxolane-2,5'-3,4,6,7,8,8a-hexahydronaphthalene]-2'-carbonitrile 在 盐酸 、 sodium tetrahydroborate 、 Crabtree's catalyst 、 二异丁基氢化铝 、 对甲苯磺酸 、 对苯二酚 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 邻二氯苯 、 甲苯 、 苯 为溶剂， 反应 85.5h， 生成 ethyl 2-[(1'R,2'S,4'aR,8'aS)-1',2',4'a-trimethylspiro[1,3-dioxolane-2,5'-3,4,6,7,8,8a-hexahydro-2H-naphthalene]-1'-yl]acetate
  参考文献：
  名称：

  Studies toward the Total Synthesis of Popolohuanone E:  Enantioselective Synthesis of 8-O-MethylpopolohuanoneE

  摘要：

  [GRAPHIC]8-O-Methylpopolohuanone E (2) was synthesized in a highly convergent manner starting from the cis-fused decalin derivative accessible from the (-)-Wieland-Miescher ketone analogue. The synthetic method features a biogenetic-type annulation of the phenolic and quinone segments to regioselectively construct the central tricyclic ring system as the key step.

  DOI：

  10.1021/ol016285h

文献信息

• Studies toward the synthesis of popolohuanone E: Synthesis of natural (+)-arenarol related to the proposed biogenetic precursor of popolohuanone E
  作者：Hideki Kawano、Masanori Itoh、Tadashi Katoh、Shiro Terashima

  DOI：10.1016/s0040-4039(97)10075-2

  日期：1997.11

  decalin segment 6 required for the total synthesis of popolohuanone E (1) was efficiently synthesized starting from the enantiomerically pure (−)-Wieland-Miescher ketone derivative 9; the method features ortho ester Claisen rearrangement of 15 and Ir-catalyzed hydrogenation of 17 (Scheme 2). Furthermore, by employing 6 as the key decalin segment, the first total synthesis of natural (+)-arenarol (2) related

  总合成popolohuanone E（1）所需的顺式十氢萘片段6是从对映体纯的（-）-Wieland-Miescher酮衍生物9开始有效合成的；该方法的特点是15的原酸酯Claisen重排和17的Ir催化加氢（方案2）。此外，通过采用6作为关键十氢萘片段，以对映选择性的方式完成了与拟议的1的生物遗传前体有关的天然（+）-芳烃（2）的第一个全合成（方案3）。
• Studies toward the Total Synthesis of Popolohuanone E:  Enantioselective Synthesis of 8-<i>O</i>-MethylpopolohuanoneE
  作者：Tadashi Katoh、Mari Nakatani、Shoji Shikita、Ruriko Sampe、Akihiro Ishiwata、Osamu Ohmori、Masahiko Nakamura、Shiro Terashima

  DOI：10.1021/ol016285h

  日期：2001.8.1

  [GRAPHIC]8-O-Methylpopolohuanone E (2) was synthesized in a highly convergent manner starting from the cis-fused decalin derivative accessible from the (-)-Wieland-Miescher ketone analogue. The synthetic method features a biogenetic-type annulation of the phenolic and quinone segments to regioselectively construct the central tricyclic ring system as the key step.