(1S,2R,5R,6R,7S,8R,10S,12S,13S,15S,17R)-7,10-Dihydroxy-10-iodomethyl-2,5,6,8,12,17-hexamethyl-15-(2,4,6-trimethyl-phenyl)-4,14,16-trioxa-bicyclo[11.3.1]heptadecane-3,9-dione | 714217-53-5

• 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: (1S,2R,5R,6R,7S,8R,10S,12S,13S,15S,17R)-7,10-Dihydroxy-10-iodomethyl-2,5,6,8,12,17-hexamethyl-15-(2,4,6-trimethyl-phenyl)-4,14,16-trioxa-bicyclo[11.3.1]heptadecane-3,9-dione
• CAS: 714217-53-5
• 化学式: C₃₀H₄₅IO₇
• 分子量: 644.588
• InChiKey: DVXTYQGHFWCLTG-SFPUXOGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  38.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  102.29
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,5R,6R,7S,8R,10S,12S,13S,15S,17R)-7,10-Dihydroxy-10-iodomethyl-2,5,6,8,12,17-hexamethyl-15-(2,4,6-trimethyl-phenyl)-4,14,16-trioxa-bicyclo[11.3.1]heptadecane-3,9-dione 在 chromium dichloride 、 sodium tetrahydroborate 、 cerium(III) chloride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 7.83h， 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
• 作为产物：
  描述：

  2-(二甲氧基甲基)-1,3,5-三甲基苯 、 (8S)-8,8a-deepoxy-8-hydroxy-8a-iodooleandonolide 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以57%的产率得到(1S,2R,5R,6R,7S,8R,10S,12S,13S,15S,17R)-7,10-Dihydroxy-10-iodomethyl-2,5,6,8,12,17-hexamethyl-15-(2,4,6-trimethyl-phenyl)-4,14,16-trioxa-bicyclo[11.3.1]heptadecane-3,9-dione
  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.