(2S,4S,5R,7R,8S)-7-chloro-4,5-dihydroxy-N,N-dimethyl-8-(3-phenylmethoxypropyl)oxocane-2-carboxamide | 934977-05-6

• 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: (2S,4S,5R,7R,8S)-7-chloro-4,5-dihydroxy-N,N-dimethyl-8-(3-phenylmethoxypropyl)oxocane-2-carboxamide
• CAS: 934977-05-6
• 化学式: C₂₀H₃₀ClNO₅
• 分子量: 399.915
• InChiKey: LFUQMQSTOKNKKC-GFEQUFNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R,7R,8S)-7-chloro-4,5-dihydroxy-N,N-dimethyl-8-(3-phenylmethoxypropyl)oxocane-2-carboxamide 在 氢氧化钾 、 L-Selectride 、 sodium hydride 、 二正丁基氧化锡 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 28.5h， 生成 1-[2-(3-benzyloxy-propyl)-6-(4-methoxy-benzyloxy)-3,8-dioxa-bicyclo[5.1.1]non-4-yl]-propan-1-ol
  参考文献：
  名称：

  Asymmetric Total Syntheses of (+)-3-(Z)-Laureatin and (+)-3-(Z)-Isolaureatin by “Lone Pair−Lone Pair Interaction-Controlled” Isomerization

  摘要：

  The first asymmetric total syntheses of the dihalogenated medium-sized dioxabicyclic marine natural products (+)-3-(Z)-isolaureatin (1) and (+)-3-(Z)-laureatin (2) have been accomplished. Notable features of the highly stereo-, regio-, and chemoselective syntheses of these alpha,alpha'-trans-oxocene natural products include an intramolecular amide enolate alkylation to construct the alpha,alpha'-cis-oxocene, novel "lone pair-lone pair interaction-controlled" epimerizations to the alpha,alpha'-trans-oxocenes, various strategies for stereoselective introduction of halogen atoms, and novel olefin cross-metatheses for construction of the (Z)-enyne systems.

  DOI：

  10.1021/ja068346i
• 作为产物：
  描述：

  在 四氧化锇 、 对甲苯磺酸 四氯化碳 、 N-甲基吲哚酮 、 3-甲基-1-环己烯 、 乙醇 、 三辛基膦 、 双(三甲基硅烷基)氨基钾 、 sodium hydride 、 二异丁基氢化铝 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 40.17h， 生成 (2S,4S,5R,7R,8S)-7-chloro-4,5-dihydroxy-N,N-dimethyl-8-(3-phenylmethoxypropyl)oxocane-2-carboxamide
  参考文献：
  名称：

  Asymmetric Total Syntheses of (+)-3-(Z)-Laureatin and (+)-3-(Z)-Isolaureatin by “Lone Pair−Lone Pair Interaction-Controlled” Isomerization

  摘要：

  The first asymmetric total syntheses of the dihalogenated medium-sized dioxabicyclic marine natural products (+)-3-(Z)-isolaureatin (1) and (+)-3-(Z)-laureatin (2) have been accomplished. Notable features of the highly stereo-, regio-, and chemoselective syntheses of these alpha,alpha'-trans-oxocene natural products include an intramolecular amide enolate alkylation to construct the alpha,alpha'-cis-oxocene, novel "lone pair-lone pair interaction-controlled" epimerizations to the alpha,alpha'-trans-oxocenes, various strategies for stereoselective introduction of halogen atoms, and novel olefin cross-metatheses for construction of the (Z)-enyne systems.

  DOI：

  10.1021/ja068346i

文献信息

• Asymmetric Total Syntheses of (+)-3-(<i>Z</i>)-Laureatin and (+)-3-(<i>Z</i>)-Isolaureatin by “Lone Pair−Lone Pair Interaction-Controlled” Isomerization
  作者：Hyoungsu Kim、Hyunjoo Lee、Dongjoo Lee、Sanghee Kim、Deukjoon Kim

  DOI：10.1021/ja068346i

  日期：2007.2.1

  The first asymmetric total syntheses of the dihalogenated medium-sized dioxabicyclic marine natural products (+)-3-(Z)-isolaureatin (1) and (+)-3-(Z)-laureatin (2) have been accomplished. Notable features of the highly stereo-, regio-, and chemoselective syntheses of these alpha,alpha'-trans-oxocene natural products include an intramolecular amide enolate alkylation to construct the alpha,alpha'-cis-oxocene, novel "lone pair-lone pair interaction-controlled" epimerizations to the alpha,alpha'-trans-oxocenes, various strategies for stereoselective introduction of halogen atoms, and novel olefin cross-metatheses for construction of the (Z)-enyne systems.