(3aS,4R,6aR,10aR)-3-Oxo-3,3a,4,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene-4-carboxylic acid (1R,2S,4S,6R,8S)-2-(diethyl-isopropyl-silanyloxy)-4-methoxy-5,7-dioxa-tricyclo[6.2.1.0^2,6]undec-9-en-10-ylmethyl ester | 461406-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (3aS,4R,6aR,10aR)-3-Oxo-3,3a,4,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene-4-carboxylic acid (1R,2S,4S,6R,8S)-2-(diethyl-isopropyl-silanyloxy)-4-methoxy-5,7-dioxa-tricyclo[6.2.1.0^2,6]undec-9-en-10-ylmethyl ester
• 英文别名: [(1R,2S,4S,6R,8S)-2-[diethyl(propan-2-yl)silyl]oxy-4-methoxy-5,7-dioxatricyclo[6.2.1.02,6]undec-9-en-10-yl]methyl (3aS,4R,6aR,10aR)-3-oxo-1,3a,4,6a,7,8,9,10-octahydrobenzo[d][2]benzofuran-4-carboxylate
• CAS: 461406-36-0
• 化学式: C₃₁H₄₆O₈Si
• 分子量: 574.787
• InChiKey: BHERMRJEEXXDTQ-GXZKBDBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3aS,4R,6aR,10aR)-3-Oxo-3,3a,4,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene-4-carboxylic acid (1R,2S,4S,6R,8S)-2-(diethyl-isopropyl-silanyloxy)-4-methoxy-5,7-dioxa-tricyclo[6.2.1.0^2,6]undec-9-en-10-ylmethyl ester 在 三乙胺 、 二氯二甲基硅烷 、 lithium hexamethyldisilazane 作用下， 以 甲苯 为溶剂， 生成 (3aR,4S,6aR,10aR)-4-[(1R,2S,4S,6R,8S,9R)-2-(Diethyl-isopropyl-silanyloxy)-4-methoxy-10-methylene-5,7-dioxa-tricyclo[6.2.1.0^2,6]undec-9-yl]-3-oxo-3,3a,4,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene-4-carboxylic acid 、 (3aR,4R,6aR,10aR)-4-[(1R,2S,4S,6R,8S,9R)-2-(Diethyl-isopropyl-silanyloxy)-4-methoxy-10-methylene-5,7-dioxa-tricyclo[6.2.1.0^2,6]undec-9-yl]-3-oxo-3,3a,4,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene-4-carboxylic acid
  参考文献：
  名称：

  Studies Aimed at the Total Synthesis of Azadirachtin. A Modeled Connection of C-8 and C-14 in Azadirachtin

  摘要：

  [GRAPHIC]Studies on the connection between the right and left segments of azadirachtin are described. The Ireland-Claisen rearrangement of Li-enolate of the modeled ester with dichlorodimethylsilane in toluene afforded the desired limonoid framework stereoselectively in good yield.

  DOI：

  10.1021/ol026260y
• 作为产物：
  描述：

  (Z)-8-Hydroxy-3-(4-methoxy-benzyloxymethyl)-oct-2-enoic acid methyl ester 在 4-二甲氨基吡啶 、 正丁基锂 、 三氟甲磺酸三甲基硅酯 、 2,6-二叔丁基-4-甲基苯酚 、 (R)-(+)-1-苯基乙醇 、 氢氟酸 、 戴斯-马丁氧化剂 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 179.5h， 生成 (3aS,4R,6aR,10aR)-3-Oxo-3,3a,4,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene-4-carboxylic acid (1R,2S,4S,6R,8S)-2-(diethyl-isopropyl-silanyloxy)-4-methoxy-5,7-dioxa-tricyclo[6.2.1.0^2,6]undec-9-en-10-ylmethyl ester
  参考文献：
  名称：

  Studies Aimed at the Total Synthesis of Azadirachtin. A Modeled Connection of C-8 and C-14 in Azadirachtin

  摘要：

  [GRAPHIC]Studies on the connection between the right and left segments of azadirachtin are described. The Ireland-Claisen rearrangement of Li-enolate of the modeled ester with dichlorodimethylsilane in toluene afforded the desired limonoid framework stereoselectively in good yield.

  DOI：

  10.1021/ol026260y

文献信息

• Studies Aimed at the Total Synthesis of Azadirachtin. A Modeled Connection of C-8 and C-14 in Azadirachtin
  作者：Takehiro Fukuzaki、Satoshi Kobayashi、Takamasa Hibi、Yohei Ikuma、Jun Ishihara、Naoki Kanoh、Akio Murai

  DOI：10.1021/ol026260y

  日期：2002.8.1

  [GRAPHIC]Studies on the connection between the right and left segments of azadirachtin are described. The Ireland-Claisen rearrangement of Li-enolate of the modeled ester with dichlorodimethylsilane in toluene afforded the desired limonoid framework stereoselectively in good yield.