(4R,5R)-1-dodecyne-4,5-diol | 546084-20-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4R,5R)-1-dodecyne-4,5-diol
• 英文别名: 1-Dodecyne-4,5-diol, (4R,5R)-；(4R,5R)-dodec-1-yne-4,5-diol
• CAS: 546084-20-2
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: GZCFGGVLYVGATN-VXGBXAGGSA-N

物化性质

• 沸点：
  327.1±22.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R,5R)-1-dodecyne-4,5-diol 在 四甲基乙二胺 、 氧气 、 对甲苯磺酸 、 copper(l) chloride 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 6.0h， 生成 6-[(4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl]-1-vinyl-2,4-hexadiynyl alcohol
  参考文献：
  名称：

  Synthesis of a new type of antitumour agent panaxytriol: Synthesis of its four diastereomers

  摘要：

  Synthesis of four diastereomers of panaxytriol has been described. The basic objective is to create two acetylenic precursors followed by cuprous chloride mediated C-C bond coupling reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00732-2
• 作为产物：
  描述：

  (2R,3S)-3-heptyloxirane methanol 在 六甲基磷酰三胺 、 高氯酸 、 水 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 96.5h， 生成 (4R,5R)-1-dodecyne-4,5-diol
  参考文献：
  名称：

  Synthesis of panaxytriol and its stereoisomers as potential antitumor drugs

  摘要：

  DOI：

  10.1016/j.tetasy.2016.03.005

文献信息

• COMPOUNDS, COMPOSITIONS AND METHODS FOR REDUCING TOXICITY AND TREATING OR PREVENTING DISEASES
  申请人：Danishefsky Samuel J.

  公开号：US20110312904A1

  公开（公告）日：2011-12-22

  The present invention provides compounds of Formula (I), compositions comprising an effective amount of a compound of Formula (I), optionally with chemotherapeutic drugs such as a tubulin-binding drug, and methods of their use for reducing the toxicity of cytotoxic agents, treating or preventing cancer or a neuropathic disorder, inducing a chemoprotective phase II enzyme, DNA, or protein synthesis, enhancing the immune system, treating inflammation, improving and enhancing general health or well-being, and methods for making compounds of Formula (I).

  本发明提供了公式(I)的化合物，以及包含公式(I)化合物的有效量的组合物，可选地与化疗药物如微管结合药物一起使用，并用于减少细胞毒性药物的毒性，治疗或预防癌症或神经病理性障碍，诱导化学保护性II期酶、DNA或蛋白质合成，增强免疫系统，治疗炎症，改善和增强整体健康或福祉，以及制备公式(I)化合物的方法。
• COMPOSITIONS AND METHODS FOR TREATING CANCER OR A NEUROTROPHIC DISORDER
  申请人：Danishefsky Samuel J.

  公开号：US20110124690A1

  公开（公告）日：2011-05-26

  The present invention relates to compositions comprising an effective amount of a Panaxytriol Compound and a tubulin-binding drug, methods for treating or preventing cancer or a neurotrophic disorder comprising administering to a subject in need thereof an effective amount of a Panaxytriol Compound and a tubulin-binding drug, and methods for making a Panaxytriol Compound.

  本发明涉及组合物，包括有效量的泛沙三醇化合物和微管结合药物，治疗或预防癌症或神经营养障碍的方法包括向需要的受体中投与有效量的泛沙三醇化合物和微管结合药物，以及制备泛沙三醇化合物的方法。
• Compounds, compositions and methods for reducing toxicity and treating or preventing diseases
  申请人：Danishefsky Samuel J.

  公开号：US08859615B2

  公开（公告）日：2014-10-14

  The present invention provides compounds of Formula (I), compositions comprising an effective amount of a compound of Formula (I), optionally with chemotherapeutic drugs such as a tubulin-binding drug, and methods of their use for reducing the toxicity of cytotoxic agents, treating or preventing cancer or a neuropathic disorder, inducing a chemoprotective phase II enzyme, DNA, or protein synthesis, enhancing the immune system, treating inflammation, improving and enhancing general health or well-being, and methods for making compounds of Formula (I).

  本发明提供公式（I）化合物，包括含有公式（I）化合物的有效量的组合物，可选地与化疗药物如微管结合药物一起使用，并用于降低细胞毒性药剂的毒性，治疗或预防癌症或神经病理性疾病，诱导化学保护期II酶、DNA或蛋白质的合成，增强免疫系统，治疗炎症，改善和增强一般健康或福祉，并提供公式（I）化合物的制备方法。
• Total Synthesis as a Resource in Drug Discovery:  The First In Vivo Evaluation of Panaxytriol and Its Derivatives
  作者：Heedong Yun、Ting-Chao Chou、Huajin Dong、Yuan Tian、Yue-ming Li、Samuel J. Danishefsky

  DOI：10.1021/jo0515475

  日期：2005.12.1

  We have conducted key preliminary studies into the in vitro and in vivo cytotoxicity of panaxytriol. Through total synthesis, we prepared and evaluated several synthetic panaxytriol analogues, each of which exhibited enhanced cytotoxicity relative to the natural product. Consequently, we have begun to chart the first in vitro SAR map for the compound, which suggests that the C-3 hydroxyl functionality is not critical for biological activity and that, in fact, engagement of the C-9-C-10 diol as an acetonide actually leads to notably enhanced cytotoxicity. Furthermore, through in vivo investigations, we demonstrated that panaxytriol and panaxytriol acetonide (12) moderately suppress tumor growth with little or no toxicity. Finally, preliminary in vitro evaluation of panaxytriol indicates that it possesses neurotrophic activity.
• Straightforward Synthesis of Panaxytriol:  An Active Component of Red Ginseng
  作者：Heedong Yun、Samuel J. Danishefsky

  DOI：10.1021/jo0341665

  日期：2003.5.1

  A total synthesis of (3R,9R,10R)-panaxytriol (1) was accomplished enantioselectively (40% overall yield; 30% for the longest sequence). A key step was a Cadiot-Chodkiewicz cross-coupling reaction on two fragments containing, in the aggregate, three unprotected hydroxyl groups. One fragment was synthesized by a highly enantioselective reduction of an enynone. The other arose from a highly enantioselective dihydroxylation of an allylic alcohol.