17,17-ethylenedioxy-3-methylenehydroxy-estra-1,3,5(10)-triene | 165609-56-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 17,17-ethylenedioxy-3-methylenehydroxy-estra-1,3,5(10)-triene
• CAS: 165609-56-3
• 化学式: C₂₁H₂₈O₃
• 分子量: 328.452
• InChiKey: JOFDQFQHICGIHP-ZRNYENFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  17,17-ethylenedioxy-3-methylenehydroxy-estra-1,3,5(10)-triene 在 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以95%的产率得到3-hydroxymethylestra-1,3,5-(10)-triene-17-one
  参考文献：
  名称：

  Estrone sulfate analogs as estrone sulfatase inhibitors

  摘要：

  The high serum concentration of estrone sulfate and the presence of estrone sulfatase in breast tumors constitute an important mechanism of local synthesis of estrogens in the tissue. Thus, inhibitors of estrone sulfatase may be effective in the treatment of estrogen-dependent breast cancer. In this study, we synthesized several isostructural analogs of estrone sulfate (estrone-3-methylsulfonate, estrone phosphate, 3-desoxyestradiol-3-methylenesulfonate, and 3-desoxyestrone-3-methylenesulfonate) and tested them on human placental sterylsulfatase. The results were (i) The K-i of 3-desoxyestrone-3-methylenesulfonate 12 and 3-desoxyestradiol-3-methylenesulfonate 7 are more than 100-fold higher than the K-i or K-M estrone sulfate, (ii) As compared to estrone sulfate, the K-i value for estrone-3-methylsulfonate 2 is about 30-fold higher, while estrone phosphate 3 is bound by the sulfatase with roughly the same affinity as estrone sulfate. The results shed some light on the electronical and sterical requirements for high affinity binding to the enzyme.

  DOI：

  10.1016/0039-128x(94)00048-h
• 作为产物：
  描述：

  estrone triflate 在 bis(triphenylphosphine) palladium (Il) acetate lithium aluminium tetrahydride 、 1,3-双(二苯基膦)丙烷 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 41.0h， 生成 17,17-ethylenedioxy-3-methylenehydroxy-estra-1,3,5(10)-triene
  参考文献：
  名称：

  Estrone sulfate analogs as estrone sulfatase inhibitors

  摘要：

  The high serum concentration of estrone sulfate and the presence of estrone sulfatase in breast tumors constitute an important mechanism of local synthesis of estrogens in the tissue. Thus, inhibitors of estrone sulfatase may be effective in the treatment of estrogen-dependent breast cancer. In this study, we synthesized several isostructural analogs of estrone sulfate (estrone-3-methylsulfonate, estrone phosphate, 3-desoxyestradiol-3-methylenesulfonate, and 3-desoxyestrone-3-methylenesulfonate) and tested them on human placental sterylsulfatase. The results were (i) The K-i of 3-desoxyestrone-3-methylenesulfonate 12 and 3-desoxyestradiol-3-methylenesulfonate 7 are more than 100-fold higher than the K-i or K-M estrone sulfate, (ii) As compared to estrone sulfate, the K-i value for estrone-3-methylsulfonate 2 is about 30-fold higher, while estrone phosphate 3 is bound by the sulfatase with roughly the same affinity as estrone sulfate. The results shed some light on the electronical and sterical requirements for high affinity binding to the enzyme.

  DOI：

  10.1016/0039-128x(94)00048-h

文献信息

• Rhodium‐Catalyzed Enantioselective Formal [4+1] Cyclization of Benzyl Alcohols and Benzaldimines: Facile Access to Silicon‐Stereogenic Heterocycles
  作者：Bingxue Shen、Deng Pan、Wanying Xie、Xiao‐Xi Li、Songjie Yu、Genping Huang、Xingwei Li

  DOI：10.1002/anie.202315230

  日期：2024.1.2

  A rhodium-catalyzed enantioselective formal [4+1] annulation of benzyl alcohols and benzaldimines with secondary silanes has been achieved in excellent enantioselectivity to afford a range of sila-O- and sila-N-heterocycles with silicon-stereogenic centers, where the rhodium catalyst plays a dual role in the O/N-Si and C-Si coupling.

  铑催化的苯甲醇和苯甲醛亚胺与仲硅烷的对映选择性形式[4+1]环化反应具有优异的对映选择性，可得到一系列具有硅立构中心的sila- O-和sila- N-杂环，其中铑催化剂在O/N-Si和C-Si耦合中发挥双重作用。