(2E)-3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-acrylic acid methyl ester | 503560-07-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E)-3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-acrylic acid methyl ester
• 英文别名: methyl (E)-3-[(4S,5S)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-phenyl-4,5-dihydro-1,3-oxazol-5-yl]prop-2-enoate
• CAS: 503560-07-4
• 化学式: C₂₀H₂₉NO₄Si
• 分子量: 375.54
• InChiKey: FBLYOJXLPLXDKX-CPQFKCLQSA-N

物化性质

• 沸点：
  434.8±30.0 °C(predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E)-3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-acrylic acid methyl ester 在 红铝 、 仲丁醇 、 copper(I) bromide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以82.4%的产率得到3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of (+)-spectaline

  摘要：

  Our synthesis of (+)-spectaline revealed that the methodology involving diastereoselective palladium(0)-catalyzed oxazoline formation and intramolecular reductive amination by catalytic hydrogenation of an oxazoline is an effective method for the asymmetric synthesis of natural products possessing complex functionalized piperidine cores. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00794-2
• 作为产物：
  描述：

  (4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazoline 在 臭氧 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.0h， 生成 (2E)-3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-acrylic acid methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of (+)-spectaline

  摘要：

  Our synthesis of (+)-spectaline revealed that the methodology involving diastereoselective palladium(0)-catalyzed oxazoline formation and intramolecular reductive amination by catalytic hydrogenation of an oxazoline is an effective method for the asymmetric synthesis of natural products possessing complex functionalized piperidine cores. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00794-2

文献信息

• Stereoselective synthesis of (+)-spectaline
  作者：Yiu-Suk Lee、Yong-Ho Shin、Yong-Hyun Kim、Kee-Young Lee、Chang-Young Oh、Sung-Jae Pyun、Hyun-Ju Park、Jin-Hyun Jeong、Won-Hun Ham

  DOI：10.1016/s0957-4166(02)00794-2

  日期：2003.1

  Our synthesis of (+)-spectaline revealed that the methodology involving diastereoselective palladium(0)-catalyzed oxazoline formation and intramolecular reductive amination by catalytic hydrogenation of an oxazoline is an effective method for the asymmetric synthesis of natural products possessing complex functionalized piperidine cores. (C) 2003 Elsevier Science Ltd. All rights reserved.