3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-(9R)-8,8a-deoxa-9-dihydrooleandonolide | 565220-26-0

• 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: 3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-(9R)-8,8a-deoxa-9-dihydrooleandonolide
• CAS: 565220-26-0
• 化学式: C₃₃H₅₀O₆
• 分子量: 542.756
• InChiKey: CMVZXFUZJBVQKZ-PNXVFXKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.99
• 重原子数：
  39.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-(9R)-8,8a-deoxa-9-dihydrooleandonolide 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以97%的产率得到(9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydrooleandonolide seco-acid
  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：

  oleandonolide 3,5-acetonide 在 chromium dichloride 、 sodium tetrahydroborate 、 cerium(III) chloride 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 18.0h， 生成 3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-(9R)-8,8a-deoxa-9-dihydrooleandonolide
  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

文献信息

• The first stereoselective total synthesis of lankanolide. Part 1: Computer-assisted design and lactonization of model seco-acid derivatives
  作者：Tatsuo Hamada、Yukinari Kobayashi、Mitsugu Kiyokawa、Osamu Yonemitsu

  DOI：10.1016/s0040-4039(03)00954-7

  日期：2003.6

  To design easily cyclizable seco-acid derivatives of lankanolide, the conformation of several model seco-acids was calculated and the lactonization experiments of the seco-acids were carried out to elucidate the efficiency of the cyclization of the model seco-acid. (C) 2003 Published by Elsevier Science Ltd.