(2S*,9R*)-(Z)-2,4-bis(pivaloyloxymethyl)oxon-5-en-3,8-dione | 244055-79-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (2S*,9R*)-(Z)-2,4-bis(pivaloyloxymethyl)oxon-5-en-3,8-dione
• 英文别名: [(2S,5Z,9R)-9-(2,2-dimethylpropanoyloxymethyl)-3,8-dioxo-4,7-dihydrooxonin-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 244055-79-6
• 化学式: C₂₀H₃₀O₇
• 分子量: 382.454
• InChiKey: ZICUNDCFUWIIIP-CMKSSICZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S*,9R*)-(Z)-2,4-bis(pivaloyloxymethyl)oxon-5-en-3,8-dione 在 三乙基硅烷 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到(2S*,3R*,8S*,9R*)-(Z)-2,9-bis(pivaloyloxymethyl)oxon-5-en-3,8-diol
  参考文献：
  名称：

  Enantioselective synthesis of the medium ring ethers, tetrahydrooxepin, oxocane and hexahydrooxonin, of ciguatoxin. Extensive ring-expansion and chemoenzymatic desymmetrization strategy

  摘要：

  The extensive ring-expansion strategy for the synthesis of tetrahydrooxepin, oxocane, and hexahydrooxonin, which correspond to the D(E), I and F rings of ciguatoxin (CTX1B, 1), respectively, has been established. Chemoenzymatic acylation of the meso alcohols using a lipase provides an expeditious entry for the enantiomeric building blocks. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00370-1
• 作为产物：
  描述：

  [(2S,5R)-5-(2,2-dimethylpropanoyloxymethyl)-3,4-dimethylideneoxolan-2-yl]methyl 2,2-dimethylpropanoate 在 三乙烯二胺 、 lead(IV) acetate 、 四氧化锇 、 四丁基氟化铵 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 吡啶 、 甲苯 、 叔丁醇 为溶剂， 反应 176.0h， 生成 (2S*,9R*)-(Z)-2,4-bis(pivaloyloxymethyl)oxon-5-en-3,8-dione
  参考文献：
  名称：

  Enantioselective synthesis of the medium ring ethers, tetrahydrooxepin, oxocane and hexahydrooxonin, of ciguatoxin. Extensive ring-expansion and chemoenzymatic desymmetrization strategy

  摘要：

  The extensive ring-expansion strategy for the synthesis of tetrahydrooxepin, oxocane, and hexahydrooxonin, which correspond to the D(E), I and F rings of ciguatoxin (CTX1B, 1), respectively, has been established. Chemoenzymatic acylation of the meso alcohols using a lipase provides an expeditious entry for the enantiomeric building blocks. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00370-1