(9R)-3,5-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydro-oleandonolide | 714217-39-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (9R)-3,5-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydro-oleandonolide
• CAS: 714217-39-7
• 化学式: C₃₀H₄₆O₆
• 分子量: 502.692
• InChiKey: MMPGAMCBPLIBNB-FYPPDWEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  36.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  85.22
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (9R)-3,5-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydro-oleandonolide 在 甲醇 、 sodium hydroxide 、 camphor-10-sulfonic acid 作用下， 以 正己烷 、 二甲基亚砜 、 苯 为溶剂， 反应 30.0h， 生成 (9R)-3,5:9,11-bis-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydrooleandonolide seco-acid methyl ester
  参考文献：
  名称：

  Computer-assisted design and lactonization of model seco-acid derivatives of lankanolide

  摘要：

  In some cases, seco-acid derivatives (a precursor of macrolactone) did not cyclize to form the corresponding macrolactone. To design easily cyclizable seco-acid derivatives of lanaknolide, the conformation of several model seco-acids was calculated, and lactonization experiments of the seco-acids prepared from oleandomycin were carried out to elucidate the efficiency of the cyclization of the model seco-acid. The easily cyclable seco-acid was designed to be C8 exomethylene derivative of lankanolide seco-acid. On the other hand, seco-acid derivative having tertiary alcohol at C8 was predicted not to cyclize to form macrolactone. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.061
• 作为产物：
  描述：

  (8S)-8,8a-deepoxy-8-hydroxy-8a-iodooleandonolide 在 chromium dichloride 、 sodium tetrahydroborate 、 cerium(III) chloride 、 camphor-10-sulfonic acid 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 13.83h， 生成 (9R)-3,5-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydro-oleandonolide
  参考文献：
  名称：

  Computer-assisted design and lactonization of model seco-acid derivatives of lankanolide

  摘要：

  In some cases, seco-acid derivatives (a precursor of macrolactone) did not cyclize to form the corresponding macrolactone. To design easily cyclizable seco-acid derivatives of lanaknolide, the conformation of several model seco-acids was calculated, and lactonization experiments of the seco-acids prepared from oleandomycin were carried out to elucidate the efficiency of the cyclization of the model seco-acid. The easily cyclable seco-acid was designed to be C8 exomethylene derivative of lankanolide seco-acid. On the other hand, seco-acid derivative having tertiary alcohol at C8 was predicted not to cyclize to form macrolactone. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.061