(1S)[1-(2′-bromoethyl)-1,5-dimethylhex-4-enyloxy]tert-butyldimethylsilane | 1528767-71-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S)[1-(2′-bromoethyl)-1,5-dimethylhex-4-enyloxy]tert-butyldimethylsilane
• 英文别名: [(3S)-1-bromo-3,7-dimethyloct-6-en-3-yl]oxy-tert-butyl-dimethylsilane
• CAS: 1528767-71-6
• 化学式: C₁₆H₃₃BrOSi
• 分子量: 349.427
• InChiKey: QBXFGGNUZNKNGZ-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  (1S)[1-(2′-bromoethyl)-1,5-dimethylhex-4-enyloxy]tert-butyldimethylsilane 在 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 20.0~80.0 ℃ 、540.01 kPa 条件下， 反应 28.08h， 生成 (S)-(+)-xanthoangelol J
  参考文献：
  名称：

  Total synthesis and assignment of the absolute stereochemistry of xanthoangelol J: development of a highly efficient method for Claisen–Schmidt condensation

  摘要：

  The first total synthesis of cancer chemopreventive terpenyl hydroxychalcone xanthoangelol J isolated from Angelica keiskei was accomplished with asymmetric epoxidation, aromatic C-alkylation and Claisen-Schmidt condensation via enol mode as key steps. The crucial Claisen-Schmidt condensation has been accomplished by a novel green method using KHSO4-SiO2 as a recyclable catalyst under microwave activation. The absolute configuration of the molecule was also determined. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.106
• 作为产物：
  描述：

  (S)-3,7-dimethyloct-6-ene-1,3-diol 在 2,6-二甲基吡啶 、 四溴化碳 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.67h， 生成 (1S)[1-(2′-bromoethyl)-1,5-dimethylhex-4-enyloxy]tert-butyldimethylsilane
  参考文献：
  名称：

  Total synthesis and assignment of the absolute stereochemistry of xanthoangelol J: development of a highly efficient method for Claisen–Schmidt condensation

  摘要：

  The first total synthesis of cancer chemopreventive terpenyl hydroxychalcone xanthoangelol J isolated from Angelica keiskei was accomplished with asymmetric epoxidation, aromatic C-alkylation and Claisen-Schmidt condensation via enol mode as key steps. The crucial Claisen-Schmidt condensation has been accomplished by a novel green method using KHSO4-SiO2 as a recyclable catalyst under microwave activation. The absolute configuration of the molecule was also determined. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.106

文献信息

• Total synthesis and assignment of the absolute stereochemistry of xanthoangelol J: development of a highly efficient method for Claisen–Schmidt condensation
  作者：Dwipen Kakati、Nabin C. Barua

  DOI：10.1016/j.tet.2013.11.106

  日期：2014.1

  The first total synthesis of cancer chemopreventive terpenyl hydroxychalcone xanthoangelol J isolated from Angelica keiskei was accomplished with asymmetric epoxidation, aromatic C-alkylation and Claisen-Schmidt condensation via enol mode as key steps. The crucial Claisen-Schmidt condensation has been accomplished by a novel green method using KHSO4-SiO2 as a recyclable catalyst under microwave activation. The absolute configuration of the molecule was also determined. (C) 2013 Elsevier Ltd. All rights reserved.