(1S,12R,13S,14R,16S,17R)-3,10-dimethoxy-15-oxahexacyclo[10.5.1.02,11.04,9.013,17.014,16]octadeca-2,4,6,8,10-pentaene-14,16-dicarboxylic acid | 291761-70-1

• 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: (1S,12R,13S,14R,16S,17R)-3,10-dimethoxy-15-oxahexacyclo[10.5.1.02,11.04,9.013,17.014,16]octadeca-2,4,6,8,10-pentaene-14,16-dicarboxylic acid
• CAS: 291761-70-1
• 化学式: C₂₁H₁₈O₇
• 分子量: 382.37
• InChiKey: YORVKHBBXROZFI-SELXWKPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,12R,13S,14R,16S,17R)-3,10-dimethoxy-15-oxahexacyclo[10.5.1.02,11.04,9.013,17.014,16]octadeca-2,4,6,8,10-pentaene-14,16-dicarboxylic acid 在 草酰氯 作用下， 以80%的产率得到(1S,12R,13S,14R,16S,17R)-3,10-dimethoxy-15-oxahexacyclo[10.5.1.02,11.04,9.013,17.014,16]octadeca-2,4,6,8,10-pentaene-14,16-dicarbonyl chloride
  参考文献：
  名称：

  New and improved ‘LEGO’ BLOCK protocols for the direct synthesis of hydrophilic ribbon molecules with acid, ester or peptide functionality

  摘要：

  Hydrophilic ribbon molecules are produced directly from the reaction of cyclobutene epoxide BLOCKs with norbornene dipolarophiles or indirectly by chemical modification of substituents in preformed lipophilic ribbon molecules. The formation of di- and tetra-acid chloride epoxides holds the key to the formation of ester, acid and amide BLOCKs which are active in 1,3-dipolar cycloadditions with norbornene dipolarophiles, thereby delivering a wide range of substituents into the ribbon molecules and opening up combinatorial opportunities at each step. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)00685-7
• 作为产物：
  描述：

  (1S,12R,13S,14R,16S,17R)-3,10-dimethoxy-15-oxahexacyclo[10.5.1.02,11.04,9.013,17.014,16]octadeca-2,4,6,8,10-pentaene-14,16-dicarbonyl chloride 在 叔丁基过氧化氢 、 氢氧化钾 、 potassium tert-butylate 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (1S,12R,13S,14R,16S,17R)-3,10-dimethoxy-15-oxahexacyclo[10.5.1.02,11.04,9.013,17.014,16]octadeca-2,4,6,8,10-pentaene-14,16-dicarboxylic acid
  参考文献：
  名称：

  New and improved ‘LEGO’ BLOCK protocols for the direct synthesis of hydrophilic ribbon molecules with acid, ester or peptide functionality

  摘要：

  Hydrophilic ribbon molecules are produced directly from the reaction of cyclobutene epoxide BLOCKs with norbornene dipolarophiles or indirectly by chemical modification of substituents in preformed lipophilic ribbon molecules. The formation of di- and tetra-acid chloride epoxides holds the key to the formation of ester, acid and amide BLOCKs which are active in 1,3-dipolar cycloadditions with norbornene dipolarophiles, thereby delivering a wide range of substituents into the ribbon molecules and opening up combinatorial opportunities at each step. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)00685-7

文献信息

• Photochemical Cycloaddition Reagents for Rigidly Attaching the 1,4-Dimethoxynaphthalene Chromophore to Scaffold Alkenes
  作者：Davor Margetic、Richard A. Russell、Ronald N. Warrener

  DOI：10.1021/ol006571d

  日期：2000.12.1

  The norbornanecyclobutene epoxides 1a-1c containing a fused 1,4-dimethoxynaphthalene chromophore have been reacted with cyclobutenes, cyclohexenes, norbornenes, 7-isopropylidenenorbornenes, 7-azanorbornenes, and other cyclic or electron-deficient alkenes at room temperature to form 1:1 adducts in stereoselective 1,3-dipolar cycloaddition reactions; alkynes can also participate in this reaction, The ability to form 2:1 adducts has also been demonstrated, thereby opening up opportunities for preparing functionalized products with large chromophore separations.