(R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)propan-1-ol | 1003609-75-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)propan-1-ol
• CAS: 1003609-75-3
• 化学式: C₁₃H₂₄O₅
• 分子量: 260.331
• InChiKey: ZBUCIVUCUWEFIO-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)propan-1-ol 、 甲氧基-三氟甲基苯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以95%的产率得到(R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)propyl (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Synthesis of the EF-Ring of Ciguatoxin 3C Based on the [2,3]-Wittig Rearrangement and Ring-Closing Olefin Metathesis

  摘要：

  The EF-ring segment of ciguatoxin 3C, a causative toxin of ciguatera fish poisoning, was synthesized in three major steps: 1,4-addition for the C20O-C27 bond connection, chirality transferring anti selective [2,3]-Wittig rearrangement for the construction of the anti-2-hydroxyalkyl ether part, and ring-closing olefin metathesis for the F-ring formation.

  DOI：

  10.1021/ol702231j
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以6.2 mg的产率得到(R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)propan-1-ol
  参考文献：
  名称：

  Synthesis of the EF-Ring of Ciguatoxin 3C Based on the [2,3]-Wittig Rearrangement and Ring-Closing Olefin Metathesis

  摘要：

  The EF-ring segment of ciguatoxin 3C, a causative toxin of ciguatera fish poisoning, was synthesized in three major steps: 1,4-addition for the C20O-C27 bond connection, chirality transferring anti selective [2,3]-Wittig rearrangement for the construction of the anti-2-hydroxyalkyl ether part, and ring-closing olefin metathesis for the F-ring formation.

  DOI：

  10.1021/ol702231j

文献信息

• Convergent synthesis of fluorescence-labeled probes of Annonaceous acetogenins and visualization of their cell distribution
  作者：Naoto Kojima、Takekuni Morioka、Daisuke Urabe、Masahiro Yano、Yuki Suga、Naoyoshi Maezaki、Ayako Ohashi-Kobayashi、Yasuyuki Fujimoto、Masatomo Maeda、Takao Yamori、Takehiko Yoshimitsu、Tetsuaki Tanaka

  DOI：10.1016/j.bmc.2010.10.004

  日期：2010.12

  The convergent synthesis of fluorescence-labeled solamin, an antitumor Annonaceous acetogenin, was accomplished by two asymmetric alkynylations of 2,5-diformyl tetrahydrofuran with an alkyne tagged with fluorescent groups and another alkyne with an alpha,beta-unsaturated gamma-lactone. Assay for the growth inhibitory activity against human cancer cell lines revealed that the probe with the fluorescent groups at the end of the hydrocarbon chain may have the same mode of action as natural acetogenins. The merged fluorescence of dansyl-labeled solamin and MitoTracker Red suggests that Annonaceous acetogenins localize in the mitochondria. (C) 2010 Elsevier Ltd. All rights reserved.