(1S,2S)-2-(3-Methoxy-phenyl)-cyclopropanecarbonyl chloride | 96728-45-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1S,2S)-2-(3-Methoxy-phenyl)-cyclopropanecarbonyl chloride
• CAS: 96728-45-9
• 化学式: C₁₁H₁₁ClO₂
• 分子量: 210.66
• InChiKey: WQXVBFOUVRGRPD-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-(3-Methoxy-phenyl)-cyclopropanecarbonyl chloride 在 硫酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 (1S,2R)-2-(3-methoxyphenyl)cyclopropane-1-carboxylic acid
  参考文献：
  名称：

  N,N-Dialkylated monophenolic trans-2-phenylcyclopropylamines: novel central 5-hydroxytryptamine-receptor agonists

  摘要：

  N,N-Dialkylated monophenolic derivatives of trans-2-phenylcyclopropylamine were synthesized and tested for central 5-hydroxytryptamine (5-HT) and dopamine (DA) receptor stimulating activity by use of a biochemical test method in rats. A hydroxy substituent in the 2- or 3-position of the phenyl ring was required for 5-HT-receptor stimulation. N,N-Diethyl or N,N-di-n-propyl substitution gave the most potent 5-HT-receptor agonists. The 4-hydroxy and 3,4-dihydroxy derivatives of trans-2-phenyl-N,N-di-n-propylcyclopropylamine were inactive at central DA and 5-HT receptors. In contrast, the corresponding 3-hydroxy derivative 18 and some of its derivatives weakly affected both DA and NE synthesis. Two of the most potent 5-HT-receptor agonists, trans-2-(2-hydroxyphenyl)-N,N-di-n-propylcyclopropylamine (8) and the 3-hydroxy isomer 18 were resolved into the enantiomers. The 1R,2S enantiomers of 8 and 18 displayed 5-HT activity, while the 1S,2R enantiomers were inactive. Compound (1R,2S)-18, but not (1R,2S)-8, weakly affected rat brain DA and NE synthesis.

  DOI：

  10.1021/jm00396a014
• 作为产物：
  描述：

  trans-1-(m-methoxyphenyl)-2-acryloylcyclopropane 在 吡啶 、 sodium periodate 、 四氧化锇 、 sodium hydrogensulfide 、 氯化亚砜 作用下， 以 水 、 丙酮 、 苯 为溶剂， 反应 2.17h， 生成 (1S,2S)-2-(3-Methoxy-phenyl)-cyclopropanecarbonyl chloride
  参考文献：
  名称：

  Total synthesis of aromatic steroids

  摘要：

  DOI：

  10.1021/jo00216a034

文献信息

• Picosecond radical kinetics. Rate constants for ring openings of 2-aryl-substituted cyclopropylcarbinyl radicals
  作者：Martin Newcomb、Seung-Yong Choi、Patrick H. Toy

  DOI：10.1139/cjc-77-5-6-1123

  日期：——

  The kinetics of ring openings of a series of eight (trans-2-arylcyclopropyl)methyl radicals (1) were studied by indirect kinetic methods using Barton's PTOC esters as radical precursors and reaction with PhSeH as the competition reaction. The substituents were CF3, F, Me, and OMe located on both the para and meta positions of the aromatic ring. Syntheses of the radical precursors and the products of the radical reactions are described. Kinetics were determined between -43 and 25 degrees C in four cases (CF, and OMe substituents) and at 0 and 25 degrees C in the other four cases. The rate constants at 25 degrees C ranged from 1.0 x 10(11) s(-1) (p-CH3) to 4.1 x 10(11) s(-1) (p-CF,). The relatively large acceleration of the p-CF3 group, ca. 2.5 times as fast as the parent system with Ar = Ph, correlates well with Adam's Delta D substituent parameters but not with other radical substituent parameters. These calibrated radical rearrangements provide a new set of ultrafast reactions that can be applied in mechanistic probe studies.