6-[(4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl]-1-vinyl-2,4-hexadiynyl alcohol | 405073-76-9

• 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: 6-[(4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl]-1-vinyl-2,4-hexadiynyl alcohol
• 英文别名: 8-[(4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl]oct-1-en-4,6-diyn-3-ol
• CAS: 405073-76-9
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: JVJTWOPEMAGFNK-OMKBGSMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  6-[(4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl]-1-vinyl-2,4-hexadiynyl alcohol 在 吡啶 、 4-二甲氨基吡啶 、 sodium methylate 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-6-((4R,5R)-5-heptyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-vinyl-hexa-2,4-diynyl ester
  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,3R)-1,2-epoxy-3-decanol 在 四甲基乙二胺 、 氧气 、 对甲苯磺酸 、 copper(l) chloride 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 、 丙酮 为溶剂， 反应 13.0h， 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

文献信息

• Synthesis and Absolute Configuration of Panaxytriol.
  作者：Mitsuru SATOH、Naoki TAKEUCHI、Yasuo FUJIMOTO

  DOI：10.1248/cpb.45.1114

  日期：——

  A diastereomeric mixture at C-3 of panaxytriol (1) was synthesized starting from L-(+)-diethyl tartrate, and the absolute configurations at C-9 and C-10 of 1 were confirmed to be 9S and 10S, respectively. The absolute configuration at C-3 of 1 was reconfirmed to be R by the application of Mosher's method.

  以L-(+)-酒石酸二乙酯为原料，合成了人参三醇(1)的C-3位非对映异构体混合物，并证实1的C-9位和C-10位绝对构型分别为9S和10S。应用Mosher方法再次确认1的C-3位点的绝对构型为R。
• 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.