(1Z,3E)-3-[iodo(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methylidene]-N-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-benzofuran-1(3H)-imine | 1408314-31-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1Z,3E)-3-[iodo(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methylidene]-N-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-benzofuran-1(3H)-imine
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[(Z)-[(3E)-3-[iodo-[(2S,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methylidene]-2-benzofuran-1-ylidene]amino]oxan-2-yl]methyl acetate
• CAS: 1408314-31-7
• 化学式: C₅₇H₅₈INO₁₅
• 分子量: 1123.99
• InChiKey: LXKDJWHHCCLVOU-JHIUQKFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  74
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  182
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  N-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-2-[(2'',3'',4'',6''-tetra-O-benzyl-α-D-mannopyranosyl)ethyn-2-yl]benzamide 在 碘 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 以94%的产率得到(1Z,3E)-3-[iodo(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methylidene]-N-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-benzofuran-1(3H)-imine
  参考文献：
  名称：

  Additions and corrections published in 2013

  摘要：

  DOI：

  10.1039/c3cc90365f

文献信息

• Iodocyclization of <i>o</i>-Alkynylbenzamides Revisited: Formation of Isobenzofuran-1(3<i>H</i>)-imines and 1<i>H</i>-Isochromen-1-imines Instead of Lactams
  作者：Claudine Schlemmer、Lars Andernach、Dieter Schollmeyer、Bernd F. Straub、Till Opatz

  DOI：10.1021/jo3017378

  日期：2012.11.16

  The iodocyclization of o-allcynylbenzamides with various electrophiles has been reported to yield five- or six-membered lactams by nucleophilic attack of the amide nitrogen onto the triple bond. While the formation of an isobenzofuran-1(3H)-imine with two bulky substituents under Larock conditions was initially attributed to steric hindrance, we found out that cyclization via the amide oxygen is the rule rather than the exception. Thus, the structures of the products reported in the literature need to be revised.