(2R)-trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene | 86782-19-6

• 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: (2R)-trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene
• 英文别名: trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]-cyclohexa-4,6-diene；5,6-diacetoxy-1-benzoyloxymethyl-1,3-cyclohexadiene；[(5R,6R)-5,6-diacetyloxycyclohexa-1,3-dien-1-yl]methyl benzoate
• CAS: 86782-19-6
• 化学式: C₁₈H₁₈O₆
• 分子量: 330.337
• InChiKey: QKUQVZOCGPQPCS-IAGOWNOFSA-N

物化性质

• 沸点：
  450.4±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R)-trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene 在 对甲苯磺酸 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 (2R)-trans-2-acetoxy-3-<(E)-cinnamoyloxy>-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene
  参考文献：
  名称：

  (±)-Zeylena 的全合成

  摘要：

  Zeylena，从 Uvaria zeylanica L.（番荔枝科）的根中分离出来，已通过 DL-trans-2,3-dihydroxy-1-(benzoyloxymethyl)cyclohexa-4,6 的分子内环加成反应合成为外消旋修饰-二烯3-(E)-肉桂酸酯或其乙酸酯。

  DOI：

  10.1246/bcsj.59.655
• 作为产物：
  描述：

  [(3R,4R,5R,6R)-6-acetyloxy-5-[tert-butyl(dimethyl)silyl]oxy-3,4-dihydroxycyclohexen-1-yl]methyl benzoate 在 四丁基氟化铵 、 N,N'-硫羰基二咪唑 、 三甲氧基磷 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 (2R)-trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene
  参考文献：
  名称：

  Enantiospecific Syntheses of (+)-Crotepoxide, (+)-Boesenoxide, (+)-β-Senepoxide, (+)-Pipoxide Acetate, (−)-iso-Crotepoxide, (−)-Senepoxide, and (−)-Tingtanoxide from (−)-Quinic Acid¹

  摘要：

  A convenient strategy that is ideally suited for the construction of all the naturally occurring cyclohexane diepoxides and cyclohexene epoxides is described. The key intermediate 12, a 1,3-cyclohexadiene, has been prepared from (-)-quinic acid in 11 steps with 18% overall yield. Singlet oxygen photooxygenation of the 1,3-cyclohexadiene followed by rearrangement of the resultant endoperoxides with either cobalt-meso-tetraphenylporphyrin or trimethyl phosphite afforded enantiopure (+)-crotepoxide, (+)-boesenoxide, and (-)-iso-crotepoxide or (-)-senepoxide, (+)-beta-senepoxide,(+)-pipoxide acetate, and (-)-tingtanoxide, respectively.

  DOI：

  10.1021/jo970907o

文献信息

• Total synthesis of (+)-pipoxide and (+)-.beta.-senepoxide and their diene precursors
  作者：Seiichiro Ogawa、Tohei Takagaki

  DOI：10.1021/jo00213a030

  日期：1985.6
• Structures of β-senepoxide, tingtanoxide, and their diene precursors. Constituents of Uvaria ferruginea
  作者：Montree Kodpinid、Chirawat Sadavongvivad、Chachanat Thebtaranonth、Yodhathai Thebtaranonth

  DOI：10.1016/s0040-4039(00)81832-8

  日期：1983.1
• Enantiospecific Syntheses of (+)-Crotepoxide, (+)-Boesenoxide, (+)-β-Senepoxide, (+)-Pipoxide Acetate, (−)-<i>iso</i>-Crotepoxide, (−)-Senepoxide, and (−)-Tingtanoxide from (−)-Quinic Acid¹
  作者：Tony K. M. Shing、Eric K. W. Tam

  DOI：10.1021/jo970907o

  日期：1998.3.1

  A convenient strategy that is ideally suited for the construction of all the naturally occurring cyclohexane diepoxides and cyclohexene epoxides is described. The key intermediate 12, a 1,3-cyclohexadiene, has been prepared from (-)-quinic acid in 11 steps with 18% overall yield. Singlet oxygen photooxygenation of the 1,3-cyclohexadiene followed by rearrangement of the resultant endoperoxides with either cobalt-meso-tetraphenylporphyrin or trimethyl phosphite afforded enantiopure (+)-crotepoxide, (+)-boesenoxide, and (-)-iso-crotepoxide or (-)-senepoxide, (+)-beta-senepoxide,(+)-pipoxide acetate, and (-)-tingtanoxide, respectively.
• Total Synthesis of (±)-Zeylena
  作者：Seiichiro Ogawa、Tohei Takagaki

  DOI：10.1246/bcsj.59.655

  日期：1986.2

  Zeylena, isolated from the roots of Uvaria zeylanica L. (Annonaceae), has been synthesized as a racemic modification by an intramolecular cyclo-addition reaction of DL-trans-2,3-dihydroxy-1-(benzoyloxymethyl)cyclohexa-4,6-diene 3-(E)-cinnamate or its acetate.

  Zeylena，从 Uvaria zeylanica L.（番荔枝科）的根中分离出来，已通过 DL-trans-2,3-dihydroxy-1-(benzoyloxymethyl)cyclohexa-4,6 的分子内环加成反应合成为外消旋修饰-二烯3-(E)-肉桂酸酯或其乙酸酯。