trans-2-(m-methylphenyl)cyclopropanemethanol | 114095-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-2-(m-methylphenyl)cyclopropanemethanol
• 英文别名: (trans-2-(3-methylphenyl)cyclopropyl)methanol；[(1S,2S)-2-(3-methylphenyl)cyclopropyl]methanol
• CAS: 114095-62-4
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: BVBZFGOPWRCASY-GHMZBOCLSA-N

物化性质

• 沸点：
  273.9±9.0 °C(predicted)
• 密度：
  1.065±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  trans-2-(m-methylphenyl)cyclopropanemethanol 以 吡啶 、 乙腈 为溶剂， 反应 44.0h， 生成 cis-<2-(m-methylphenyl)cyclopronyl>methyl acetate
  参考文献：
  名称：

  Arylcyclopropane photochemistry. Unusual aromatic substituent effects on the photochemical rearrangement of (2-arylcyclopropyl)methyl acetates to 1-arylhomoallyl acetates

  摘要：

  DOI：

  10.1021/ja00219a040
• 作为产物：
  描述：

  ethyl trans-2-(m-methylphenyl)cyclopropane-1-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 6.0h， 生成 trans-2-(m-methylphenyl)cyclopropanemethanol
  参考文献：
  名称：

  Arylcyclopropane photochemistry. Unusual aromatic substituent effects on the photochemical rearrangement of (2-arylcyclopropyl)methyl acetates to 1-arylhomoallyl acetates

  摘要：

  DOI：

  10.1021/ja00219a040

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.
• Chiral recyclable fluorous disulfonamide ligand for catalytic enantioselective cyclopropanation of allylic alcohols
  作者：Yuya Kawashima、Tetsuya Ezawa、Mai Yamamura、Taisuke Harada、Takuya Noguchi、Tsuyoshi Miura、Nobuyuki Imai

  DOI：10.1016/j.tet.2015.09.024

  日期：2015.11

  Allylic alcohols reacted with Et2Zn and CH2I2 in the presence of a catalytic amount of fluorous disulfonamide 3a to afford the corresponding cyclopropylmethanols in 69%-quantitative yields with 49-85% ee. Recovery of the fluorous ligand 3a was readily performed from the reaction mixture by the fluorous solid-phase extraction (FSPE), and the recovered 3a could be reused without a significant loss of the catalytic activity and enantioselectivity. (C) 2015 Elsevier Ltd. All rights reserved.
• US7169797B2
  申请人：——

  公开号：US7169797B2

  公开（公告）日：2007-01-30