(S)-{4-(tert-butyl-dimethyl-silanyloxy)-2-[2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)-acetyl]-phenyl}-carbamic acid tert-butyl ester | 229032-21-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-{4-(tert-butyl-dimethyl-silanyloxy)-2-[2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)-acetyl]-phenyl}-carbamic acid tert-butyl ester
• 英文别名: (S)-{4-(tert-butyldimethylsilanyloxy)-2-[2-(2,2-dimethyl-5-oxo[1,3]dioxolan-4-yl)acetyl]phenyl}carbamic acid tert-butyl ester
• CAS: 229032-21-7
• 化学式: C₂₄H₃₇NO₇Si
• 分子量: 479.646
• InChiKey: GVOFKBFGUSKAHZ-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  100.16
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-{4-(tert-butyl-dimethyl-silanyloxy)-2-[2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)-acetyl]-phenyl}-carbamic acid tert-butyl ester 在 吡啶 、 氟化氢吡啶 、 苯甲醚 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 9.0h， 生成 (S)-2-(biphenyl-4-yl)-N-{2-[2-(2,2-dimethyl-5-oxo[1,3]dioxolan-4-yl)acetyl]-4-hydroxyphenyl}acetamide
  参考文献：
  名称：

  Synthesis of fluorescent molecular probes specific for the receptor of blepharismone, a mating-inducing pheromone of the ciliate Blepharisma japonicum

  摘要：

  Blepharismone (gamone 2) is a mating-inducing pheromone of the ciliate Blepharisma japonicum. N-Pyrenylbutyryl-blepharismone and N-biphenylacetyl-blepharismone, which are fluorescent derivatives of blepharismone, were synthesized as molecular probes for the gamone 2 receptor. Further, we proved that they have inhibitory activities against the blepharismone-induced monotypic pairing of B. japonicum. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2006.12.021
• 作为产物：
  描述：

  (S)-[2,2-二甲基-5-氧代二氧戊环-4-基]乙酸 在 草酰氯 、 叔丁基锂 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 反应 4.83h， 生成 (S)-{4-(tert-butyl-dimethyl-silanyloxy)-2-[2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)-acetyl]-phenyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Practical synthesis of blepharismone, a mating inducing pheromone of Blepharisma japonicum

  摘要：

  Both enantiomers of blepharismone, a mating inducing pheromone produced by type II cells of Blepharisma japonicum, were synthesized via the Stille cross-coupling. reaction of [4-(tert-butyl-dimethyl-silanyloxy)-2-trimethylstannanyl-phenyl]-carbamic acid tert-butyl ester with an acid chloride derived from (S)- and (R)-malic acid as a key reaction. The mating inducing activity of synthetic (S)-blepharismone was as effective as that of the natural one. The enantiomer (R)-blepharismone showed no mating inducing activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.005