(4S,7E,10S,13E,15S,16S)-15-hydroxy-4,10,16-trimethyl-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,12-trione | 344614-27-3

• 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: (4S,7E,10S,13E,15S,16S)-15-hydroxy-4,10,16-trimethyl-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,12-trione
• CAS: 344614-27-3
• 化学式: C₁₆H₂₂O₇
• 分子量: 326.346
• InChiKey: LHDGUPDIEZSEGS-PNFBGWSTSA-N

物化性质

• 沸点：
  624.7±55.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4S,7E,10S,13E,15S,16S)-15-hydroxy-4,10,16-trimethyl-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,12-trione 在 偶氮二甲酸二异丙酯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 (+)-macrosphelide C
  参考文献：
  名称：

  First total synthesis of macrosphelides C and F

  摘要：

  Macrosphelides C and F were synthesized by lactonization of 14-oxo seco acids at the O(10)-C(11) bond followed by reduction and Mitsunobu inversion of the resulting hydroxyl group. The seco acids were prepared from the corresponding furans by furan ring-opening with NBS followed by further oxidation of the 4-oxo-2-alkenals with NaClO2. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00285-4
• 作为产物：
  描述：

  (2S,6S)-2-(2-furyl)-6-hydroxy-3-oxa-4-heptanone 在 4-二甲氨基吡啶 、 sodium chlorite 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 2-甲基-2-丁烯 、 camphor-10-sulfonic acid 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 acetate buffer 、 水 、 丙酮 、 甲苯 、 叔丁醇 为溶剂， 反应 34.0h， 生成 (4S,7E,10S,13E,15S,16S)-15-hydroxy-4,10,16-trimethyl-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,12-trione
  参考文献：
  名称：

  First total synthesis of macrosphelides C and F

  摘要：

  Macrosphelides C and F were synthesized by lactonization of 14-oxo seco acids at the O(10)-C(11) bond followed by reduction and Mitsunobu inversion of the resulting hydroxyl group. The seco acids were prepared from the corresponding furans by furan ring-opening with NBS followed by further oxidation of the 4-oxo-2-alkenals with NaClO2. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00285-4

文献信息

• Synthesis of Various Macrosphelides by Oxidative Derivatization of the Macrosphelide Core
  作者：Hideo Nemoto、Yuji Matsuya、Takanori Kawaguchi

  DOI：10.3987/com-03-s26

  日期：——

  The macrosphelide core (4), simple 16-membered trilactone, was subjected to several oxidative conditions to produce various natural macrosphelide analogues, including macrosphelides A and C. This approach provided a new access to diverse macrosphelides for a study on their structure-activity relationships.

  大球体核心 (4)，简单的 16 元三内酯，经受多种氧化条件以产生各种天然大球体类似物，包括大球体 A 和 C。这种方法为研究各种大球体的构效关系提供了新途径.
• A Combinatorial Synthesis of a Macrosphelide Library Utilizing a Palladium-Catalyzed Carbonylation on a Polymer Support
  作者：Takashi Takahashi、Shin-ichi Kusaka、Takayuki Doi、Toshiaki Sunazuka、Satoshi Ōmura

  DOI：10.1002/anie.200352229

  日期：2003.11.3
• First total synthesis of macrosphelides C and F
  作者：Yuichi Kobayashi、Hukum P Acharya

  DOI：10.1016/s0040-4039(01)00285-4

  日期：2001.4

  Macrosphelides C and F were synthesized by lactonization of 14-oxo seco acids at the O(10)-C(11) bond followed by reduction and Mitsunobu inversion of the resulting hydroxyl group. The seco acids were prepared from the corresponding furans by furan ring-opening with NBS followed by further oxidation of the 4-oxo-2-alkenals with NaClO2. (C) 2001 Elsevier Science Ltd. All rights reserved.