[(4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol | 130967-61-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• 英文别名: (2S,3S)-2,3-methylethylidenedioxy-1-decanol
• CAS: 130967-61-2
• 化学式: C₁₃H₂₆O₃
• 分子量: 230.348
• InChiKey: TXKJTKYRFLXCCH-VXGBXAGGSA-N

物化性质

• 沸点：
  305.0±17.0 °C(Predicted)
• 密度：
  0.929±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol 在 吡啶 、 盐酸 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (2R,3R)-1,2-epoxy-3-decanol
  参考文献：
  名称：

  First Total Synthesis of Panaxytriol, a Potent Antitumor Agent Isolated from Panax Ginseng

  摘要：

  首次合成了从三七中分离出来的一种强效抗肿瘤药物--三七三醇 1，并确认其立体结构为 (3R,9R,10R)-十七碳-1-烯-4,6-二炔-3,9,10-三醇。

  DOI：

  10.1055/s-1998-1775
• 作为产物：
  描述：

  (2R,3R)-1,2,3-Trihydroxydecane 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 [(4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
  参考文献：
  名称：

  Total Synthesis as a Resource in Drug Discovery:  The First In Vivo Evaluation of Panaxytriol and Its Derivatives

  摘要：

  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.

  DOI：

  10.1021/jo0515475

文献信息

• Syntheses of two diastereoisomers of panaxytriol, a potent antitumor agent isolated from panax ginseng
  作者：Wei Lu、Guangrong Zheng、Daxin Gao、Junchao Cai

  DOI：10.1016/s0040-4020(99)00352-x

  日期：1999.6

  (3R, 9R, 10R) and (3R, 9S, 10S) diastereoisomers (2 and 3) of panaxytriol (1) were synthesized, and the absolute configuration of panaxytriol was confirmed as (3R, 9R, 10R)-heptadec-1-ene-4,6-diyne-3,9,10-triol. (C) 1999 Elsevier Science Ltd. All rights reserved.

  (3R, 9R, 10R) 和 (3R, 9S, 10S) 对映异构体 (2 和 3) 的PA3（panaxytriol）通过合成得到了，并确认了PA3的绝对构型为(3R, 9R, 10R)-heptadec-1-en-4,6-diyne-3,9,10-triol。 © 1999 Elsevier Science Ltd. 保留所有权利。
• First Total Synthesis of Panaxytriol, a Potent Antitumor Agent Isolated from <i>Panax</i> <i>Ginseng</i>
  作者：Wei Lu、Guangrong Zheng、Junchao Cai

  DOI：10.1055/s-1998-1775

  日期：1998.7

  Panaxytriol 1, a potent antitumor agent isolated from Panax ginseng, was first synthesized, and its stereostructure was confirmed to be (3R,9R,10R)-heptadec-1-ene-4,6-diyne-3,9,10-triol.

  首次合成了从三七中分离出来的一种强效抗肿瘤药物--三七三醇 1，并确认其立体结构为 (3R,9R,10R)-十七碳-1-烯-4,6-二炔-3,9,10-三醇。
• Synthesis of a new type of antitumour agent panaxytriol: Synthesis of its four diastereomers
  作者：Mukund K Gurjar、V Sylesh Kumar、B Venkateswara Rao

  DOI：10.1016/s0040-4020(99)00732-2

  日期：1999.10

  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.
• An efficient method for the alkylation of chiral triflates with alkynyllithium reagents. A highly concise total synthesis of (+)-panaxacol
  作者：Hiyoshizo Kotsuki、Isao Kadota、Masamitsu Ochi

  DOI：10.1016/s0040-4039(00)97688-3

  日期：1990.1
• KOTSUKI, HIYOSHIZO;KADOTA, ISAO;OCHI, MASAMITSU, TETRAHEDRON LETT., 31,(1990) N2, C. 4609-4612
  作者：KOTSUKI, HIYOSHIZO、KADOTA, ISAO、OCHI, MASAMITSU

  DOI：——

  日期：——