(2R,3S)-2-benzyl-3-(chloromethyl)oxirane | 1381874-36-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S)-2-benzyl-3-(chloromethyl)oxirane
• CAS: 1381874-36-7
• 化学式: C₁₀H₁₁ClO
• 分子量: 182.65
• InChiKey: GNPMBYCVBRWOHS-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-benzyl-3-(chloromethyl)oxirane 在 sodium 作用下， 以 乙醚 为溶剂， 反应 6.0h， 以80%的产率得到(R)-1-phenylbut-3-en-2-ol
  参考文献：
  名称：

  Stereoselective synthesis of alpinoid-C and its analogues and study of their cytotoxic activity against cancer cell lines

  摘要：

  A simple, highly efficient and stereoselective synthetic route has been developed for synthesis of alpinoid-C (1) and its analogues (2, 3 and 4) from commercially available starting materials by using Wittig olefination, Sharpless asymmetric epoxidation, Grubbs cross metathesis as key steps. All the compounds showed moderate anti-proliferative activity against human leukemia/carcinoma (U-937, THP-1, COLO-205 and HepG2) and mouse melanoma (B16-F10) cancer cell lines. Compounds 3 and 4 are found to be most potent with an IC50 of 7.53 mu M and 32.26 mu M on THP-1, 11.12 mu M and 7.21 mu M on COLO-205 cell lines, respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.021
• 作为产物：
  描述：

  [(2R,3R)-3-(苯基甲基)环氧乙烷-2-基]甲醇 在 四氯化碳 、 碳酸氢钠 、 三苯基膦 作用下， 反应 2.0h， 以90%的产率得到(2R,3S)-2-benzyl-3-(chloromethyl)oxirane
  参考文献：
  名称：

  Stereoselective synthesis of alpinoid-C and its analogues and study of their cytotoxic activity against cancer cell lines

  摘要：

  A simple, highly efficient and stereoselective synthetic route has been developed for synthesis of alpinoid-C (1) and its analogues (2, 3 and 4) from commercially available starting materials by using Wittig olefination, Sharpless asymmetric epoxidation, Grubbs cross metathesis as key steps. All the compounds showed moderate anti-proliferative activity against human leukemia/carcinoma (U-937, THP-1, COLO-205 and HepG2) and mouse melanoma (B16-F10) cancer cell lines. Compounds 3 and 4 are found to be most potent with an IC50 of 7.53 mu M and 32.26 mu M on THP-1, 11.12 mu M and 7.21 mu M on COLO-205 cell lines, respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.021