8β-tert-butyldimethylsilyloxy-(17E)-[1-(4-bromophenyl)methylidene]-de-A,B-androstane | 282724-84-9

• 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: 8β-tert-butyldimethylsilyloxy-(17E)-[1-(4-bromophenyl)methylidene]-de-A,B-androstane
• 英文别名: [(1E,3aR,4S,7aS)-1-[(4-bromophenyl)methylidene]-7a-methyl-3,3a,4,5,6,7-hexahydro-2H-inden-4-yl]oxy-tert-butyl-dimethylsilane
• CAS: 282724-84-9
• 化学式: C₂₃H₃₅BrOSi
• 分子量: 435.52
• InChiKey: KVXPXCFRRLWHBC-GYZPSSCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.82
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8β-tert-butyldimethylsilyloxy-(17E)-[1-(4-bromophenyl)methylidene]-de-A,B-androstane 在 palladium diacetate 重铬酸吡啶 、 1,3-双(二苯基膦)丙烷 、 氢氟酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 乙腈 为溶剂， 反应 24.5h， 生成 (17Z)-{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
• 作为产物：
  描述：

  4-溴苄基亚磷酸二乙酯 、 8β-[(tert-butyldimethylsilyl)oxy]de-A,B-androstan-17β-one 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以13%的产率得到8β-tert-butyldimethylsilyloxy-(17E)-[1-(4-bromophenyl)methylidene]-de-A,B-androstane
  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.