(Z,1S,2R,6R)-4-(2-chloroethylidene)-1-fluoro-2,6-bis(triisopropylsilyloxy)cyclohexane | 359761-69-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (Z,1S,2R,6R)-4-(2-chloroethylidene)-1-fluoro-2,6-bis(triisopropylsilyloxy)cyclohexane
• CAS: 359761-69-6
• 化学式: C₂₆H₅₂ClFO₂Si₂
• 分子量: 507.32
• InChiKey: WBZXQWSTXZPEGN-PLUOUREKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (Z,1S,2R,6R)-4-(2-chloroethylidene)-1-fluoro-2,6-bis(triisopropylsilyloxy)cyclohexane 在 正丁基锂 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 反应 21.0h， 生成 2α-fluoro-19-nor-1α,3β-bis(triisopropylsilyloxy)-25-(trimethylsilyloxy)-22-oxavitamin D₃
  参考文献：
  名称：

  Catalytic asymmetric synthesis and anticancer effects of the novel non-calcemic analog of vitamin D, 2α-fluoro-19-nor-22-oxa-1α,25-dihydroxyvitamin D3 in metastatic lung carcinoma

  摘要：

  1 alpha,25-Dihydroxyvitamin D-3 (1 alpha,25-D-3) has potent antiproliferative and anti-invasive properties in vitro in cancer cells. However, the major limitation to its clinical use is that it causes hypercalcemia. Therefore, vitamin D analogs with potent cell regulatory effects but with weaker calcemic effects than 1 alpha,25-D-3 are required. Among them, 22-oxa-1 alpha,25-D-3 and 19-nor-1 alpha,25-D-3 have anti-cancer effects with relatively low calcemic effects. Modifications at the C-2ot position of the A-ring also produced analogs with a unique biological profile. Not only the side-chain but also the A-ring modification thus generates a unique analog with potent cell regulatory effects and low calcemic activity as well. We report here that the hybrid 1 alpha,25-D-3 analog, synthesized via the highly regio- and stereo-selective ring opening 2 alpha-fluorination and catalytic asymmetric carbonyl-ene cyclization, with 2 alpha-fluoro, 19-nor, and 22-oxa modification exhibits unique cell regulatory activities against the development of metastatic lung carcinoma. (c) 2007 Published by Elsevier B.V.

  DOI：

  10.1016/j.jfluchem.2007.03.002
• 作为产物：
  描述：

  (Z,1R,2S,3R)-5-[2-(benzyloxy)ethylidene]-2-fluoro-3-triisopropylsilyloxy-1-cyclohexanol 在 2,6-二甲基吡啶 、 N-氯代丁二酰亚胺 、 二甲基硫 、 氨 、 lithium 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 2.75h， 生成 (Z,1S,2R,6R)-4-(2-chloroethylidene)-1-fluoro-2,6-bis(triisopropylsilyloxy)cyclohexane
  参考文献：
  名称：

  Catalytic asymmetric synthesis and anticancer effects of the novel non-calcemic analog of vitamin D, 2α-fluoro-19-nor-22-oxa-1α,25-dihydroxyvitamin D3 in metastatic lung carcinoma

  摘要：

  1 alpha,25-Dihydroxyvitamin D-3 (1 alpha,25-D-3) has potent antiproliferative and anti-invasive properties in vitro in cancer cells. However, the major limitation to its clinical use is that it causes hypercalcemia. Therefore, vitamin D analogs with potent cell regulatory effects but with weaker calcemic effects than 1 alpha,25-D-3 are required. Among them, 22-oxa-1 alpha,25-D-3 and 19-nor-1 alpha,25-D-3 have anti-cancer effects with relatively low calcemic effects. Modifications at the C-2ot position of the A-ring also produced analogs with a unique biological profile. Not only the side-chain but also the A-ring modification thus generates a unique analog with potent cell regulatory effects and low calcemic activity as well. We report here that the hybrid 1 alpha,25-D-3 analog, synthesized via the highly regio- and stereo-selective ring opening 2 alpha-fluorination and catalytic asymmetric carbonyl-ene cyclization, with 2 alpha-fluoro, 19-nor, and 22-oxa modification exhibits unique cell regulatory activities against the development of metastatic lung carcinoma. (c) 2007 Published by Elsevier B.V.

  DOI：

  10.1016/j.jfluchem.2007.03.002