(S)-{2-[2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)-acetyl]-4-hydroxy-phenyl}-carbamic acid tert-butyl ester | 229032-22-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-{2-[2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)-acetyl]-4-hydroxy-phenyl}-carbamic acid tert-butyl ester
• CAS: 229032-22-8
• 化学式: C₁₈H₂₃NO₇
• 分子量: 365.383
• InChiKey: XLZBUGMVAKOXRO-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  111.16
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-{2-[2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)-acetyl]-4-hydroxy-phenyl}-carbamic acid tert-butyl ester 、 甲酸 在 乙酸酐 作用下， 反应 1.5h， 生成 (2S)-4-(2-formamido-5-hydroxyphenyl)-2-hydroxy-4-oxobutanoic acid
  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
• 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 、 氟化氢吡啶 、 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 6.83h， 生成 (S)-{2-[2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)-acetyl]-4-hydroxy-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

文献信息

• Practical synthesis of blepharismone, a mating inducing pheromone of Blepharisma japonicum
  作者：Hisashi Takihiro、Yoshiyuki Uruma、Yoshinosuke Usuki、Akio Miyake、Hideo Iio

  DOI：10.1016/j.tetasy.2006.09.005

  日期：2006.9

  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.