(9R)-9-dihydro-3,5:9,11-bis-O-(2,4,6-trimethylbenzylidene)-oleandonolide | 565220-27-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: (9R)-9-dihydro-3,5:9,11-bis-O-(2,4,6-trimethylbenzylidene)-oleandonolide
• CAS: 565220-27-1
• 化学式: C₄₀H₅₆O₇
• 分子量: 648.88
• InChiKey: SPSYFAQASWNLDG-IHAHPTBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.09
• 重原子数：
  47.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  75.75
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (9R)-9-dihydro-3,5:9,11-bis-O-(2,4,6-trimethylbenzylidene)-oleandonolide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以85%的产率得到(2S,3R,4S,5R,6R,8S,10R,11S,12R,13R)-2,4,6,8,10,12-hexamethyl-3,5:9,11-bis-(2,4,6-trimethylbenzylidenedioxy)-tetradecane-1,8,13-triol
  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 sodium tetrahydroborate 、 camphor-10-sulfonic acid 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 异丙醇 为溶剂， 反应 11.58h， 生成 (9R)-9-dihydro-3,5:9,11-bis-O-(2,4,6-trimethylbenzylidene)-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

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.