[(2S,4aS)-6-methoxy-1,4a-dimethyl-3,4,9,10-tetrahydro-2H-phenanthren-2-yl]oxy-(bromomethyl)-dimethylsilane | 197156-92-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: [(2S,4aS)-6-methoxy-1,4a-dimethyl-3,4,9,10-tetrahydro-2H-phenanthren-2-yl]oxy-(bromomethyl)-dimethylsilane
• CAS: 197156-92-6
• 化学式: C₂₀H₂₉BrO₂Si
• 分子量: 409.439
• InChiKey: BYEKDDUFXOSDAO-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.53
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(2S,4aS)-6-methoxy-1,4a-dimethyl-3,4,9,10-tetrahydro-2H-phenanthren-2-yl]oxy-(bromomethyl)-dimethylsilane 在 咪唑 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三丁基氯化锡 、 双氧水 、 sodium cyanoborohydride 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 30.0h， 生成 Imidazole-1-carbothioic acid O-[(1S,2S,4aS,10aR)-1-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-2-yl] ester
  参考文献：
  名称：

  A general asymmetric access to the podocarpane diterpenoids

  摘要：

  An efficient and enantiocontrolled total synthesis of (+)-O-methylpodocarpic acid 2 has been accomplished by employing a combined strategy of the lipase-mediated kinetic resolution of the tricyclic allyl alcohol (+/-)-7 and a highly diastereoselective silylmethyl radical cyclization of 5 leading to the tetracyclic silyl ether 4. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00347-9
• 作为产物：
  描述：

  1,4a-dimethyl-6-methoxy-4,4a,9,10-tetrahydro-2(3H)-phenanthrenone 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 [(2S,4aS)-6-methoxy-1,4a-dimethyl-3,4,9,10-tetrahydro-2H-phenanthren-2-yl]oxy-(bromomethyl)-dimethylsilane
  参考文献：
  名称：

  A general asymmetric access to the podocarpane diterpenoids

  摘要：

  An efficient and enantiocontrolled total synthesis of (+)-O-methylpodocarpic acid 2 has been accomplished by employing a combined strategy of the lipase-mediated kinetic resolution of the tricyclic allyl alcohol (+/-)-7 and a highly diastereoselective silylmethyl radical cyclization of 5 leading to the tetracyclic silyl ether 4. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00347-9

文献信息

• A general asymmetric access to the podocarpane diterpenoids
  作者：Yoko Fujiwara、Toshihiro Yamato、Toshikazu Bando、Kozo Shishido

  DOI：10.1016/s0957-4166(97)00347-9

  日期：1997.8

  An efficient and enantiocontrolled total synthesis of (+)-O-methylpodocarpic acid 2 has been accomplished by employing a combined strategy of the lipase-mediated kinetic resolution of the tricyclic allyl alcohol (+/-)-7 and a highly diastereoselective silylmethyl radical cyclization of 5 leading to the tetracyclic silyl ether 4. (C) 1997 Published by Elsevier Science Ltd.