(Z)-2-(1-hydroxydiphenylmethyl)-3-dimethylphenylsilylpropenal

• 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: (Z)-2-(1-hydroxydiphenylmethyl)-3-dimethylphenylsilylpropenal
• 英文别名: (Z)-3-[dimethyl(phenyl)silyl]-2-[hydroxy(diphenyl)methyl]prop-2-enal
• 化学式: C₂₄H₂₄O₂Si
• 分子量: 372.539
• InChiKey: QLPUWMTTWOUCBH-ZBJSNUHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  一氧化碳 、 二甲基苯基硅烷 、 1,1-二苯基-2-丙炔-1-醇 在 dodecacarbonyltetrarhodium(0) 作用下， 以 苯 为溶剂， 100.0 ℃ 、2.03 MPa 条件下， 反应 8.0h， 以56%的产率得到2-(dimethylphenylsilylmethyl)-3,3-diphenylpropenal
  参考文献：
  名称：

  Rhodium-catalyzed transformation of propargyl alcohol derivatives to 2-silylmethyl-2-alkenals

  摘要：

  Propargyl-type alcohols (6) and the corresponding esters of carbonic acid (4) or acetic acid (5) react with two equivalents of Me2PhSiH in the presence of catalytic amounts of Rh-4(CO)(12) under CO pressure at 100 degrees C to give 2-(dimethylphenylsiIylmethyl)-2-alkenals (3), whereas 2-substituted-3-(dimethylphenylsilyl)propenals (7, 8 and 9) are also isolated with the concomitant formation of 3 when a similar reaction is operated with shortage of Me2PhSiH or with lowering of reaction temperature. The isolated 9 is selectively converted to 3 by the Rh-4(CO)(12) catalyzed reaction with Me2PhSiH under CO pressure. This fact suggests that the transformation of 4, 5 or 6 to 3 is accomplished by either a one-pot procedure or a stepwise procedure relayed by 7, 8 or 9. Usefulness of this protocol is demonstrated by the synthesis of 18 in which ethisterone (17) is directly converted by a one-pot procedure. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(98)00933-4

文献信息

• Rhodium-catalyzed transformation of propargyl alcohol derivatives to 2-silylmethyl-2-alkenals
  作者：Isamu Matsuda、Nakayoshi Niikawa、Rika Kuwabara、Hirofumi Inoue、Hideo Nagashima、Kenji Itoh

  DOI：10.1016/s0022-328x(98)00933-4

  日期：1999.2

  Propargyl-type alcohols (6) and the corresponding esters of carbonic acid (4) or acetic acid (5) react with two equivalents of Me2PhSiH in the presence of catalytic amounts of Rh-4(CO)(12) under CO pressure at 100 degrees C to give 2-(dimethylphenylsiIylmethyl)-2-alkenals (3), whereas 2-substituted-3-(dimethylphenylsilyl)propenals (7, 8 and 9) are also isolated with the concomitant formation of 3 when a similar reaction is operated with shortage of Me2PhSiH or with lowering of reaction temperature. The isolated 9 is selectively converted to 3 by the Rh-4(CO)(12) catalyzed reaction with Me2PhSiH under CO pressure. This fact suggests that the transformation of 4, 5 or 6 to 3 is accomplished by either a one-pot procedure or a stepwise procedure relayed by 7, 8 or 9. Usefulness of this protocol is demonstrated by the synthesis of 18 in which ethisterone (17) is directly converted by a one-pot procedure. (C) 1999 Elsevier Science S.A. All rights reserved.