(2S,3S,4Z)-2,3-(isopropylidenedioxy)-dodeca-4,11-dien-1-ol | 864863-33-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4Z)-2,3-(isopropylidenedioxy)-dodeca-4,11-dien-1-ol
• CAS: 864863-33-2
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: VHGDOBNCDPFCPD-VSERSJBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4Z)-2,3-(isopropylidenedioxy)-dodeca-4,11-dien-1-ol 在 三苯基膦 作用下， 以 四氯化碳 为溶剂， 反应 16.0h， 以91%的产率得到(2R,3S,4Z)-1-chloro-2,3-(isopropylidenedioxy)-dodeca-4,11-diene
  参考文献：
  名称：

  The first total synthesis of naturally occurring (+)-gymnasterkoreayne F and its enantiomer

  摘要：

  The first total synthesis of naturally occurring (+)-gymnasterkoreayne F and its enantiomer is reported. The seven-step route to these two polyacetylenes in enantiomerically pure form involves the use of (+)-2,3-O-isopropylidene-L-threitol and (-)-2,3-O-isopropylidene-D-threitol, respectively, as the starting material and a Cadiot-Chodkiewicz reaction as a key step. The absolute configuration of (+)-gymnasterkoreayne F has been confirmed to be (2E,8S,Z). The natural product and its enantiomer have been found to exhibit modest cytotoxicity against the 60 human tumor cell lines of the National Cancer Institute. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.015
• 作为产物：
  描述：

  8-溴-1-辛烯 在 potassium tert-butylate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 157.0h， 生成 (2S,3S,4Z)-2,3-(isopropylidenedioxy)-dodeca-4,11-dien-1-ol
  参考文献：
  名称：

  The first total synthesis of naturally occurring (+)-gymnasterkoreayne F and its enantiomer

  摘要：

  The first total synthesis of naturally occurring (+)-gymnasterkoreayne F and its enantiomer is reported. The seven-step route to these two polyacetylenes in enantiomerically pure form involves the use of (+)-2,3-O-isopropylidene-L-threitol and (-)-2,3-O-isopropylidene-D-threitol, respectively, as the starting material and a Cadiot-Chodkiewicz reaction as a key step. The absolute configuration of (+)-gymnasterkoreayne F has been confirmed to be (2E,8S,Z). The natural product and its enantiomer have been found to exhibit modest cytotoxicity against the 60 human tumor cell lines of the National Cancer Institute. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.015

文献信息

• The first total synthesis of naturally occurring (+)-gymnasterkoreayne F and its enantiomer
  作者：Adriano Carpita、Silvia Braconi、Renzo Rossi

  DOI：10.1016/j.tetasy.2005.06.015

  日期：2005.7

  The first total synthesis of naturally occurring (+)-gymnasterkoreayne F and its enantiomer is reported. The seven-step route to these two polyacetylenes in enantiomerically pure form involves the use of (+)-2,3-O-isopropylidene-L-threitol and (-)-2,3-O-isopropylidene-D-threitol, respectively, as the starting material and a Cadiot-Chodkiewicz reaction as a key step. The absolute configuration of (+)-gymnasterkoreayne F has been confirmed to be (2E,8S,Z). The natural product and its enantiomer have been found to exhibit modest cytotoxicity against the 60 human tumor cell lines of the National Cancer Institute. (C) 2005 Elsevier Ltd. All rights reserved.