(17E)-{1-[4-(methyloxycarbonyl)phenyl]methylidene}-de-A,B-androstan-8-one | 282724-87-2

• 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: (17E)-{1-[4-(methyloxycarbonyl)phenyl]methylidene}-de-A,B-androstan-8-one
• 英文别名: methyl 4-[(E)-[(3aR,7aS)-7a-methyl-4-oxo-2,3,3a,5,6,7-hexahydroinden-1-ylidene]methyl]benzoate
• CAS: 282724-87-2
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: SWSZQMFFQNZWKN-WJQQLCIQSA-N

物化性质

• 熔点：
  102-103 °C
• 沸点：
  450.7±28.0 °C(predicted)
• 密度：
  1.158±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (17E)-{1-[4-(methyloxycarbonyl)phenyl]methylidene}-de-A,B-androstan-8-one 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 26.75h， 生成 (17E)-1α-20-[4-(dimethylhydroxymethyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D₃
  参考文献：
  名称：

  Synthesis of New Aromatic (C17−C20)-Locked Side-Chain Analogues of Calcitriol (1α,25-Dihydroxyvitamin D₃)^,1

  摘要：

  The synthesis of four new analogues of calcitriol (1 alpha ,25-(OH)(2)-D-3) possessing aromatic and conjugated double bond units at the side chain are described. The triene system is introduced using the Lythgoe-Hoffmann La Roche convergent Wittig-Horner approach. The key steps in the preparation of the requisite upper fragments are the introduction of the side chain with the E-conjugated aromatic system and its photochemical conversion to the Z counterpart.

  DOI：

  10.1021/jo000579j
• 作为产物：
  描述：

  8β-tert-butyldimethylsilyloxy-(17E)-{1-[4-(methyloxycarbonyl)phenyl]methylidene}-de-A,B-androstane 在 重铬酸吡啶 、 氢氟酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 11.0h， 生成 (17E)-{1-[4-(methyloxycarbonyl)phenyl]methylidene}-de-A,B-androstan-8-one
  参考文献：
  名称：

  Synthesis of New Aromatic (C17−C20)-Locked Side-Chain Analogues of Calcitriol (1α,25-Dihydroxyvitamin D₃)^,1

  摘要：

  The synthesis of four new analogues of calcitriol (1 alpha ,25-(OH)(2)-D-3) possessing aromatic and conjugated double bond units at the side chain are described. The triene system is introduced using the Lythgoe-Hoffmann La Roche convergent Wittig-Horner approach. The key steps in the preparation of the requisite upper fragments are the introduction of the side chain with the E-conjugated aromatic system and its photochemical conversion to the Z counterpart.

  DOI：

  10.1021/jo000579j

文献信息

• Synthesis of New Aromatic (C17−C20)-Locked Side-Chain Analogues of Calcitriol (1α,25-Dihydroxyvitamin D₃)^,¹
  作者：Ana Fernández-Gacio、Cristian Vitale、Antonio Mouriño

  DOI：10.1021/jo000579j

  日期：2000.10.1

  The synthesis of four new analogues of calcitriol (1 alpha ,25-(OH)(2)-D-3) possessing aromatic and conjugated double bond units at the side chain are described. The triene system is introduced using the Lythgoe-Hoffmann La Roche convergent Wittig-Horner approach. The key steps in the preparation of the requisite upper fragments are the introduction of the side chain with the E-conjugated aromatic system and its photochemical conversion to the Z counterpart.